Arylaldehydes - Sigma-Aldrich
Transcript of Arylaldehydes - Sigma-Aldrich
NO
PO
STA
GE
NE
CE
SS
AR
Y IF
MA
ILED
IN T
HE
UN
ITE
D S
TATE
S
BU
SIN
ES
S R
EP
LY M
AIL
FIR
ST
-CLA
SS
MA
IL PE
RM
IT N
O.3038 S
T.LOU
IS, M
O
PO
STA
GE
WILL B
E PA
ID B
Y A
DD
RE
SS
EE
SIG
MA
P.O.B
OX
14508S
T.LOU
IS, M
O, U
SA
63178-9916
NewArylaldehydes
Global Bulk
Manufacturing
❖
Combikits™
(Vials or
Titerplates)
❖
Arylaldehyde
Resins
for SPOS
❖
Over 80 New
Products!
Organic SynthesisBuilding Blocks for
TO ORDER
PHONE
FAX
800-558-9160 (USA)or 414-273-3850
800-962-9591 (USA)or 414-273-4979
Aldrich Chemical CompanyP.O. Box 2060Milwaukee, WI 53201
ArgentinaSigma-Aldrich de Argentina, S.ATel: 54 11 4807 0321Fax: 54 11 4807 0346E-mail: [email protected]
AustraliaSigma-Aldrich Pty., LimitedFree Tel: 1-800-800-097Free Fax: 1-800-800-096Tel: 61-2-9841-0555Fax: 61-2-9841-0500E-mail: [email protected]
AustriaSigma-Aldrich Handels GmbHTel: 43 1 605 8110Fax: 43 1 605 8120E-mail: [email protected]
BelgiumSigma-Aldrich nv/saFree Tel: 0800-147.47Free Fax: 0800-147.45Tel: 03 899.13.01Fax: 03 899.13.11E-mail: [email protected]
BrazilSigma-Aldrich Química Brasil Ltda.Tel: 55-11-231-1866Fax: 55-11-257-9079E-mail: [email protected]
CanadaSigma-Aldrich Canada Ltd.Free Tel: 800-565-1400Free Fax: 800-265-3858Tel: 905-829-9500Fax: 905-829-9292E-mail: [email protected]
Czech RepublicSigma-Aldrich s.r.o.Tel: 00-420-2-2176 1300Fax: 00-420-2-2176 3300E-mail:[email protected]
DenmarkSigma-Aldrich Denmark A/STel: +45 43 56 59 10Fax: +45 43 56 59 05E-mail: [email protected]
EireSigma-Aldrich Ireland Ltd.Free Tel: 1 800 200 888Free Fax: 1 800 600 222Tel: 01 404 1900Fax: 01 404 1910E-mail: [email protected]
FinlandSigma-Aldrich FinlandTel: (09) 350-9250Fax: (09) 350-92555E-mail: [email protected]
FranceSigma-Aldrich Chimie S.a.r.lTel Numero Vert: 0800 21 14 08Fax Numero Vert: 0800 03 10 52E-mail: [email protected]
Germany(also SE Europe, the Baltics, Africa and theMiddle East)Sigma-Aldrich Chemie GmbHFreecall Tel: 0800-5155 000Freecall Fax: 0800-6490 000Tel: +49(0)89-6513-0Fax: +49(0)89-6513-1169E-mail: [email protected] Slovakia, Africa, Middle East and other European countries:Tel: +49(0)89-6513-1807Fax: +49(0)89-6513-1877
GreeceSigma-Aldrich (o.m) Ltd.Tel: 30-1-9948010Fax: 30-1-9943831E-mail: [email protected]
HungarySigma-Aldrich KftTel: 06-1-269-6474Fax: 06-1-235-9050E-mail: [email protected]
IndiaSigma-Aldrich CorporationBangalore location:Phone: 91 80 851 8797Fax: 91 80 851 8358
New Delhi location:Phone: (011) 689 9826Fax: (011) 689 9827E-mail: [email protected]
IsraelSigma Israel Chemicals Ltd.Toll Free Tel: 1-800-70-2222Tel: 972-8-948-4222Fax: 972-8-948-4200E-mail: [email protected]
ItalySigma-Aldrich S.r.l.Numero Verde: 800-827018Tel: 02-33417.310Fax: 02-38010.737E-mail: [email protected]
JapanSigma-Aldrich Japan K.K.Tel: 81-3-5821-3111Fax: 81-3-5821-3170
KoreaSigma-Aldrich KoreaToll Free Tel: 080-023-7111Toll Free Fax: 080-023-8111Tel: 82-2-783-5211Fax: 82-2-783-5011E-mail: [email protected]
MalaysiaSigma-Aldrich (M) Sdn BhdTel: 03-7824181, 03-7808140Fax: 03-7824067E-mail: [email protected]
MexicoSigma-Aldrich Química, S.A. de C.V.Tel Gratis: 91-800-0075300Tel: (72) 76 1600Fax: (72) 76 1601E-mail: [email protected]
NetherlandsSigma-Aldrich Chemie BVTel Gratis: 0800 022 9088Fax Gratis: 0800 022 9089Tel: 078-620 54 11Fax: 078-620 54 21E-mail: [email protected]
NorwaySigma-Aldrich Norway ASTel: 47 23 176 000Fax: 47 23 176 010E-mail: [email protected]
PolandSigma-Aldrich Sp.zo.oTel: (48-61) 823-24-81Fax: (48-61) 823-27-81E-mail: [email protected]
PortugalSigma-Aldrich Quimica S.A.Free Tel: 0800-202180Free Fax: 0800-202178E-mail, encomendas:[email protected]
RussiaSigma-Aldrich RussiaTel: 7-095-975-3321Fax: 7-095-975-4792E-mail: [email protected]
SingaporeSigma-Aldrich Pte., Ltd.Tel: (65) 271 1089Fax: (65) 271 1571E-mail: [email protected]
South AfricaSigma-Aldrich South Africa (Pty) Ltd.Tel: (011) 397 8886Fax: (011) 397 8859E-mail: [email protected]
SpainSigma-Aldrich Química S.A.Free Tel: 900-101376Free Fax: 900-102028Tel: 91-6619977Fax: 91-6619642E-mail, pedidos:[email protected]
SwedenSigma-Aldrich Sweden ABTel: 020-35 05 10Fax: 020-35 25 22Outside Sweden Tel: 46-8-742 4200Outside Sweden Fax: 46-8-742 4243E-mail: [email protected]
SwitzerlandAldrich ChemieA division of Fluka Chemie AGTel: 081-755 27 23Fax: 081-755 28 40Swiss Free Call: 0800 80 00 80E-mail: [email protected]
United KingdomSigma-Aldrich Company Ltd.Free Tel: 0800 717181Free Fax: 0800 378538Tel: 01202 733114Fax: 01202 715460E-mail: [email protected]
United StatesAldrich Chemical Company, Inc.Toll Free Tel: 1-800-558-9160Toll Free Fax: 1-800-962-9591Tel: 414-273-3850Fax: 414-273-4979E-mail: [email protected]
Sigma Chemical CompanyToll Free Tel: 1-800-521-8956Toll Free Fax: 1-800-325-5052Tel: 314-771-5765Fax: 314-771-5757E-mail: [email protected]
© 2000 Sigma-Aldrich Co. Printed in USA. Aldrich brand products are sold through Sigma-Aldrich, Inc. Sigma-Aldrich, Inc. warrants that its products conform to the information contained in thisand other Sigma-Aldrich publications. Purchaser must determine the suitability of the product(s) for their particular use. Additional terms and conditions may apply. Please see reverse side of theinvoice or packing slip. Aldrich is a registered trademark of Sigma-Aldrich. Riedel-de Haën®: trademark under license from Riedel-de Haën GmbH.
World Headquarters: 1001 W. St. Paul Ave., Milwaukee,WI 53233 USA • (001) 414-273-3850 • www.sigma-aldrich.com
Biochemicals and Reagents for Life Science Research
Specialty Chemicalsand Analytical
Reagents for Research
Laboratory Chemicalsand Reagents for
Research and Analysis
Chromatography Products for Analysis
and Purification
Organics and Inorganics for
Chemical Synthesis
The SIGMA-ALDRICHFamily
DUG
For Development/Manufacturing Quantities For Quantity Pricing/Standing OrdersContact your local Sigma-Aldrich office Contact your local Sigma-Aldrich officeand ask for Sigma-Aldrich Fine Chemicals
P.O. Box 355Milwaukee, WI 53201USA
Return Service Requested
Sigma-Aldrich Worldwide Locations
Mas
terc
ard
, Vis
a, a
nd
Am
eric
an E
xpre
ss a
ccep
ted
. N
O m
inim
um
ord
er O
R c
on
firm
ing
pu
rch
ase
ord
er r
equ
ired
.
ChemFiles Vol. 1, No. 2 • 2001Dess–Martin Periodinane
is widely used for the mild
oxidation of alcohols to
aldehydes and ketones.1
This reagent is especially useful
for substrates containing sensitive
functional groups and offers an
alternative to other mild
reagents (e.g. TPAP). Other
advantages such as selectivity,
rapid rates, avoiding the use of
toxic (i.e. chromium-based)
chemicals, using stoichiometric
amounts of reagent, and ease of
work up make the Dess–Martin
periodinane a reliable and easy-to-
use oxidizer in organic synthesis.
Dess–Martin PeriodinaneDess–Martin Periodinane
1. Useful in the preparation of epimerization-sensitive optically active N-protected α-amino aldehydes with high enantiomeric excess.2
2. Oximes and tosylhydrazones are converted to their corresponding carbonyl compounds under mild conditionswithout overoxidation of the final product.3
3. Oxidation of sugar hydroxyls in good yields with periodinane avoids the use of ruthenium dioxide.4
4. A highly unstable dialdehyde was prepared by oxidation with periodinane and trapped in situ with a pre-formed Wittig ylide.5
5. A convenient route to the preparation of highly reactive acyl nitroso compounds. These products can be trapped by dienes to form cycloadducts.6
6. Rapid production of complex and diverse natural product-like polycycles. A proposed mechanism starts with an ortho-oxidation followed by an intramolecular hetero Diels–Alder reaction.7
7. Neutral and mild work-up conditions avoid the formation of dehydrofluorinated by-products in the oxidation of polyfluorinated primary alcohols to aldehydes.8
27,462-3 Dess-Martin periodinane, 97% 1g; 5g[1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one]
Preparation of ArylaldehydesPreparation of ArylaldehydesVarious routes are available for the formation of arylaldehydes, including classical aromatic formylation viaVilsmeier, Gatterman, or Reimer–Tiemann reactions. Other methods include reduction of carboxylic acid derivatives,especially the reduction of esters with DIBAH9, and the oxidation of alcohols, typically with chromium reagents but accomplished under mild conditions with TPAP10 or Dess-Martin periodinane (see above).
33,074-4 Tetrapropylammonium perruthenate, 97% (TPAP) 250mg; 1g25,681-1 Diisobutylaluminum hydride (DIBAH) 100g; 1kg19,014-4 Pyridinium chlorochromate, 98% (PCC) 25g; 100g; 500g21,469-8 Pyridinium dichromate, 98% (PDC) 5g; 100g 500g
References: (1) Dess, D.B; Martin, J. C. J. Org. Chem. 1983, 48, 4155. (2) Myers, A.G. et al. Tetrahedron Lett. 2000, 41, 1359. (3) Bose, D.S.; Narsaiah, A. V. Synth. Commun.1999, 29, 937. (4) Rao, H. S. P. et al. Indian J. Chem., Sect. B. 1997, 36B, 816. (5) Barrett, A. G.M. et al. J. Org. Chem. 1997, 62, 9376. (6) Jenkins, N. E. et al. Synth. Commun.2000, 30, 947. (7) Nicolaou, K.C. et al. Angew. Chem., Int. Ed. Engl. 2000, 39, 622. (8) Lévêque, L. et al. Tetrahedron Lett. 1998. 39, 8857. (9) Winterfeldt, E. Synthesis1975, 617. (10) Ley, S.V. et al. ibid. 1994, 639.
NO
PO
STA
GE
NE
CE
SS
AR
Y IF
MA
ILED
IN T
HE
UN
ITE
D S
TATE
S
BU
SIN
ES
S R
EP
LY M
AIL
FIR
ST
-CLA
SS
MA
IL PE
RM
IT N
O.3038 S
T.LOU
IS, M
O
PO
STA
GE
WILL B
E PA
ID B
Y A
DD
RE
SS
EE
SIG
MA
P.O.B
OX
14508S
T.LOU
IS, M
O, U
SA
63178-9916
NewArylaldehydes
Global Bulk
Manufacturing
❖
Combikits™
(Vials or
Titerplates)
❖
Arylaldehyde
Resins
for SPOS
❖
Over 80 New
Products!
Organic SynthesisBuilding Blocks for
TO ORDER
PHONE
FAX
800-558-9160 (USA)or 414-273-3850
800-962-9591 (USA)or 414-273-4979
Aldrich Chemical CompanyP.O. Box 2060Milwaukee, WI 53201
ArgentinaSigma-Aldrich de Argentina, S.ATel: 54 11 4807 0321Fax: 54 11 4807 0346E-mail: [email protected]
AustraliaSigma-Aldrich Pty., LimitedFree Tel: 1-800-800-097Free Fax: 1-800-800-096Tel: 61-2-9841-0555Fax: 61-2-9841-0500E-mail: [email protected]
AustriaSigma-Aldrich Handels GmbHTel: 43 1 605 8110Fax: 43 1 605 8120E-mail: [email protected]
BelgiumSigma-Aldrich nv/saFree Tel: 0800-147.47Free Fax: 0800-147.45Tel: 03 899.13.01Fax: 03 899.13.11E-mail: [email protected]
BrazilSigma-Aldrich Química Brasil Ltda.Tel: 55-11-231-1866Fax: 55-11-257-9079E-mail: [email protected]
CanadaSigma-Aldrich Canada Ltd.Free Tel: 800-565-1400Free Fax: 800-265-3858Tel: 905-829-9500Fax: 905-829-9292E-mail: [email protected]
Czech RepublicSigma-Aldrich s.r.o.Tel: 00-420-2-2176 1300Fax: 00-420-2-2176 3300E-mail:[email protected]
DenmarkSigma-Aldrich Denmark A/STel: +45 43 56 59 10Fax: +45 43 56 59 05E-mail: [email protected]
EireSigma-Aldrich Ireland Ltd.Free Tel: 1 800 200 888Free Fax: 1 800 600 222Tel: 01 404 1900Fax: 01 404 1910E-mail: [email protected]
FinlandSigma-Aldrich FinlandTel: (09) 350-9250Fax: (09) 350-92555E-mail: [email protected]
FranceSigma-Aldrich Chimie S.a.r.lTel Numero Vert: 0800 21 14 08Fax Numero Vert: 0800 03 10 52E-mail: [email protected]
Germany(also SE Europe, the Baltics, Africa and theMiddle East)Sigma-Aldrich Chemie GmbHFreecall Tel: 0800-5155 000Freecall Fax: 0800-6490 000Tel: +49(0)89-6513-0Fax: +49(0)89-6513-1169E-mail: [email protected] Slovakia, Africa, Middle East and other European countries:Tel: +49(0)89-6513-1807Fax: +49(0)89-6513-1877
GreeceSigma-Aldrich (o.m) Ltd.Tel: 30-1-9948010Fax: 30-1-9943831E-mail: [email protected]
HungarySigma-Aldrich KftTel: 06-1-269-6474Fax: 06-1-235-9050E-mail: [email protected]
IndiaSigma-Aldrich CorporationBangalore location:Phone: 91 80 851 8797Fax: 91 80 851 8358
New Delhi location:Phone: (011) 689 9826Fax: (011) 689 9827E-mail: [email protected]
IsraelSigma Israel Chemicals Ltd.Toll Free Tel: 1-800-70-2222Tel: 972-8-948-4222Fax: 972-8-948-4200E-mail: [email protected]
ItalySigma-Aldrich S.r.l.Numero Verde: 800-827018Tel: 02-33417.310Fax: 02-38010.737E-mail: [email protected]
JapanSigma-Aldrich Japan K.K.Tel: 81-3-5821-3111Fax: 81-3-5821-3170
KoreaSigma-Aldrich KoreaToll Free Tel: 080-023-7111Toll Free Fax: 080-023-8111Tel: 82-2-783-5211Fax: 82-2-783-5011E-mail: [email protected]
MalaysiaSigma-Aldrich (M) Sdn BhdTel: 03-7824181, 03-7808140Fax: 03-7824067E-mail: [email protected]
MexicoSigma-Aldrich Química, S.A. de C.V.Tel Gratis: 91-800-0075300Tel: (72) 76 1600Fax: (72) 76 1601E-mail: [email protected]
NetherlandsSigma-Aldrich Chemie BVTel Gratis: 0800 022 9088Fax Gratis: 0800 022 9089Tel: 078-620 54 11Fax: 078-620 54 21E-mail: [email protected]
NorwaySigma-Aldrich Norway ASTel: 47 23 176 000Fax: 47 23 176 010E-mail: [email protected]
PolandSigma-Aldrich Sp.zo.oTel: (48-61) 823-24-81Fax: (48-61) 823-27-81E-mail: [email protected]
PortugalSigma-Aldrich Quimica S.A.Free Tel: 0800-202180Free Fax: 0800-202178E-mail, encomendas:[email protected]
RussiaSigma-Aldrich RussiaTel: 7-095-975-3321Fax: 7-095-975-4792E-mail: [email protected]
SingaporeSigma-Aldrich Pte., Ltd.Tel: (65) 271 1089Fax: (65) 271 1571E-mail: [email protected]
South AfricaSigma-Aldrich South Africa (Pty) Ltd.Tel: (011) 397 8886Fax: (011) 397 8859E-mail: [email protected]
SpainSigma-Aldrich Química S.A.Free Tel: 900-101376Free Fax: 900-102028Tel: 91-6619977Fax: 91-6619642E-mail, pedidos:[email protected]
SwedenSigma-Aldrich Sweden ABTel: 020-35 05 10Fax: 020-35 25 22Outside Sweden Tel: 46-8-742 4200Outside Sweden Fax: 46-8-742 4243E-mail: [email protected]
SwitzerlandAldrich ChemieA division of Fluka Chemie AGTel: 081-755 27 23Fax: 081-755 28 40Swiss Free Call: 0800 80 00 80E-mail: [email protected]
United KingdomSigma-Aldrich Company Ltd.Free Tel: 0800 717181Free Fax: 0800 378538Tel: 01202 733114Fax: 01202 715460E-mail: [email protected]
United StatesAldrich Chemical Company, Inc.Toll Free Tel: 1-800-558-9160Toll Free Fax: 1-800-962-9591Tel: 414-273-3850Fax: 414-273-4979E-mail: [email protected]
Sigma Chemical CompanyToll Free Tel: 1-800-521-8956Toll Free Fax: 1-800-325-5052Tel: 314-771-5765Fax: 314-771-5757E-mail: [email protected]
© 2000 Sigma-Aldrich Co. Printed in USA. Aldrich brand products are sold through Sigma-Aldrich, Inc. Sigma-Aldrich, Inc. warrants that its products conform to the information contained in thisand other Sigma-Aldrich publications. Purchaser must determine the suitability of the product(s) for their particular use. Additional terms and conditions may apply. Please see reverse side of theinvoice or packing slip. Aldrich is a registered trademark of Sigma-Aldrich. Riedel-de Haën®: trademark under license from Riedel-de Haën GmbH.
World Headquarters: 1001 W. St. Paul Ave., Milwaukee,WI 53233 USA • (001) 414-273-3850 • www.sigma-aldrich.com
Biochemicals and Reagents for Life Science Research
Specialty Chemicalsand Analytical
Reagents for Research
Laboratory Chemicalsand Reagents for
Research and Analysis
Chromatography Products for Analysis
and Purification
Organics and Inorganics for
Chemical Synthesis
The SIGMA-ALDRICHFamily
DUG
For Development/Manufacturing Quantities For Quantity Pricing/Standing OrdersContact your local Sigma-Aldrich office Contact your local Sigma-Aldrich officeand ask for Sigma-Aldrich Fine Chemicals
P.O. Box 355Milwaukee, WI 53201USA
Return Service Requested
Sigma-Aldrich Worldwide Locations
Mas
terc
ard
, Vis
a, a
nd
Am
eric
an E
xpre
ss a
ccep
ted
. N
O m
inim
um
ord
er O
R c
on
firm
ing
pu
rch
ase
ord
er r
equ
ired
.
ChemFiles Vol. 1, No. 2 • 2001Dess–Martin Periodinane
is widely used for the mild
oxidation of alcohols to
aldehydes and ketones.1
This reagent is especially useful
for substrates containing sensitive
functional groups and offers an
alternative to other mild
reagents (e.g. TPAP). Other
advantages such as selectivity,
rapid rates, avoiding the use of
toxic (i.e. chromium-based)
chemicals, using stoichiometric
amounts of reagent, and ease of
work up make the Dess–Martin
periodinane a reliable and easy-to-
use oxidizer in organic synthesis.
Dess–Martin PeriodinaneDess–Martin Periodinane
1. Useful in the preparation of epimerization-sensitive optically active N-protected α-amino aldehydes with high enantiomeric excess.2
2. Oximes and tosylhydrazones are converted to their corresponding carbonyl compounds under mild conditionswithout overoxidation of the final product.3
3. Oxidation of sugar hydroxyls in good yields with periodinane avoids the use of ruthenium dioxide.4
4. A highly unstable dialdehyde was prepared by oxidation with periodinane and trapped in situ with a pre-formed Wittig ylide.5
5. A convenient route to the preparation of highly reactive acyl nitroso compounds. These products can be trapped by dienes to form cycloadducts.6
6. Rapid production of complex and diverse natural product-like polycycles. A proposed mechanism starts with an ortho-oxidation followed by an intramolecular hetero Diels–Alder reaction.7
7. Neutral and mild work-up conditions avoid the formation of dehydrofluorinated by-products in the oxidation of polyfluorinated primary alcohols to aldehydes.8
27,462-3 Dess-Martin periodinane, 97% 1g; 5g[1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one]
Preparation of ArylaldehydesPreparation of ArylaldehydesVarious routes are available for the formation of arylaldehydes, including classical aromatic formylation viaVilsmeier, Gatterman, or Reimer–Tiemann reactions. Other methods include reduction of carboxylic acid derivatives,especially the reduction of esters with DIBAH9, and the oxidation of alcohols, typically with chromium reagents but accomplished under mild conditions with TPAP10 or Dess-Martin periodinane (see above).
33,074-4 Tetrapropylammonium perruthenate, 97% (TPAP) 250mg; 1g25,681-1 Diisobutylaluminum hydride (DIBAH) 100g; 1kg19,014-4 Pyridinium chlorochromate, 98% (PCC) 25g; 100g; 500g21,469-8 Pyridinium dichromate, 98% (PDC) 5g; 100g 500g
References: (1) Dess, D.B; Martin, J. C. J. Org. Chem. 1983, 48, 4155. (2) Myers, A.G. et al. Tetrahedron Lett. 2000, 41, 1359. (3) Bose, D.S.; Narsaiah, A. V. Synth. Commun.1999, 29, 937. (4) Rao, H. S. P. et al. Indian J. Chem., Sect. B. 1997, 36B, 816. (5) Barrett, A. G.M. et al. J. Org. Chem. 1997, 62, 9376. (6) Jenkins, N. E. et al. Synth. Commun.2000, 30, 947. (7) Nicolaou, K.C. et al. Angew. Chem., Int. Ed. Engl. 2000, 39, 622. (8) Lévêque, L. et al. Tetrahedron Lett. 1998. 39, 8857. (9) Winterfeldt, E. Synthesis1975, 617. (10) Ley, S.V. et al. ibid. 1994, 639.
Arylaldehydes
54,264-4 Mol. Wt.C8H7FO2 154.14
1g5g
O
H
F
O
52,681-9 Mol. Wt.C8H7FO3 170.14
1g
O
HO
F
HO
51,513-2 Mol. Wt.C8H7FO 138.14
5g
O
H
F
51,832-8 Mol. Wt.C8H7NO3 165.15
1g
O
H
NO2
52,898-6 Mol. Wt.C8H7FO2 154.14
25g
O
H
O F
51,576-0 Mol. Wt.C8H7NO4 181.15
5g
O
H
O
O2N
52,662-2 Mol. Wt.C8H6ClFO 172.58
1g5g
O
H
F
Cl
53,673-3 Mol. Wt.C8H7FO2 154.14
1g5g
O
H
F
O
51,642-2 Mol. Wt.C8H7NO4 181.15
5g
O
H
O
NO2
51,383-0 Mol. Wt.C9H7NO 145.16
5g
NH
O
H
52,661-4 Mol. Wt.C8H6ClFO 172.58
1g5g
O
H
Cl
F
52,310-0 Mol. Wt.C8H7FO2 154.14
1g5g
O
H
O
F
52,311-9 Mol. Wt.C8H8OS 152.22
5g
O
H
S
52,306-2 Mol. Wt.C9H8O 132.16
5g
O
H
52,923-0 Mol. Wt.C8H6F2O2 172.12
5g
O
H
OCF2H
52,314-3 Mol. Wt.C8H7FO 138.14
5g
O
H
F
51,286-9 Mol. Wt.C8H9BO4 179.97
5g25g
O
H
B(OH)2
O
51,874-3 Mol. Wt.C9H6BrNO 224.06
5g
NH
O
HBr
34,854-6 Mol. Wt.C9H9FO3 184.16
1g
O
H
O
O
F
51,806-9 Mol. Wt.C9H10O 134.18
1g5g
O
H
51,805-0 Mol. Wt.
C9H10O 134.18
5g
O
H
52,640-1 Mol. Wt.C9H4F6O 242.12
1g5g
O
H
CF3F3C
53,307-6 Mol. Wt.C9H6ClNO 179.60
5g
NH
O
HCl
51,575-2 Mol. Wt.C9H9BrO2 229.08
5g
O
H
O
Br
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
51,515-9 Mol. Wt.C9H10O 134.18
5g
O
H
51,535-3 Mol. Wt.C9H10O 134.18
1g5g
O
H
49,385-6 Mol. Wt.C9H10O 134.18
1g5g
O
H
54,382-9 Mol. Wt.C10H4FNO5 237.14
1g
O
O
H
O
F
NO2
51,631-7 Mol. Wt.C9H10O2 150.18
1g5g
O
H
O
54,372-1 Mol. Wt.C10H6ClFO2 212.60
1g
O
O
H
Cl
F
54,362-4 Mol. Wt.C10H5FO3 192.15
1g
O
O
H
O
F
51,632-5 Mol. Wt.C9H10O2 150.18
5g
Arylaldehyde chemistry has led to a wealth of diverse products, so naturally Aldrich is determined to offer thewidest possible breadth of substitution patterns. Target molecules prepared from groups of arylaldehydes haveincluded aminoindenes,1 quinolines,2 arylglycines,3 and homoallylic alcohols.4 With over 400 arylaldehydes amongthe more than 80,000 products in stock at Sigma-Aldrich, chances are you’ll find what you’re looking for!
(1) Katritzky, A. R. et al. J. Org. Chem. 2000, 65, 8066. (2) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977. (3) Beller, M. et al. J. Org. Chem. 1998, 63,5658. (4) Curran, D.P.; Zhiyong, L. Med. Chem. Res. 1998, 8, 261. 1. What type of chemistry do you routinely perform?
❍ General Organic Chemistry [ORGS] ❍ Organometallics [ORGM]❍ Organic Combinatorial [COCH] ❍ Polymer Chemistry [POLY]❍ Chiral Chemistry [CHIR] ❍ Drug Discovery [DRUG]
2. Please check any of the following FREE catalog and literature piecesthat you would like to receive.❍ Aldrich Handbook [002]❍ Sigma General Catalog [001]❍ Fluka/Riedel-de-Haën® Catalog [003]❍ Aldrichimica Acta [032]❍ Resins for Combichem [DLW]❍ Combikits™/Small Sample Service [CBJ]❍ Polymer Products CD [DGQ]❍ New Fluorinated Products [DEO]❍ Products for Suzuki Coupling [DTK]
3. What other specialized grouping would be of interest to you?❍ Oxidizing agents [3AA] ❍ Terminal alkenes [3AE]❍ Reducing agents [3AB] ❍ Sulfonyl chlorides [3AF]❍ Oximes [3AC] ❍ Nitriles [3AG]❍ Terminal alkynes [3AD] ❍ Other _____________________
4. ❍ I would like to receive a FREE CD-ROM with product listingsfrom the Sigma-Aldrich Library of Rare Chemicals. [DDH]
Fluka/Riedel-de-Haën and Combikits are a registered trademark and trademark, respectively, of Sigma-Aldrich Co.
Purpald®, an aminotriazole, continues to be useful as a complexation reagent for the spectrophotomeric determination of aldehydes, e.g., in drug concentrationanalyses and in determining airborne formaldehyde.Ketones, esters, formic acid, amides, hydroxylamines,quinones, uric acid, hydrazines and aminophenols do not react with Purpald® to yield purple products.1-2
For properties, procedure for detecting aldehydes, applications, and references of Purpald®, please contact our Technical Services department at 800-231-8327(USA)or your local office and request Aldrich Technical Bulletin#AL-145; or visit our Web site, www.sigma-aldrich.com/aldrichand click on Technical Bulletins.
16,289-2 Purpald®, 99+%(4-amino-3-hydrazino-5-mercapto-1,2,4-triazole)
5g; 25g; 100g
53,145-6 Mol. Wt.C5H3ClO2 130.53
1g
OCl
O
H
49,990-0 Mol. Wt.C5H5BO3S 155.97
1g5g
S
O
H
B(OH)2
51,405-5 Mol. Wt.C5H5BO3S 155.97
1g5g
S(HO)2B
H
O
49,991-9 Mol. Wt.C5H5BO3S 155.97
1g5g
S
O
H
B(OH)2
52,642-8 Mol. Wt.C7H3ClF2O 176.55
1g5g
O
H
F
Cl
F
52,391-7 Mol. Wt.C7H4Cl2O 175.01
5g
O
H
Cl
Cl
52,919-2 Mol. Wt.C7H3F3O 160.10
1mL5mL
O
H
F
F
F
54,331-4 Mol. Wt.C7H4FIO 250.01
1g
O
H
F
I
52,917-6 Mol. Wt.C7H3F3O 160.10
5mL
O
H
F
F
F
53,724-1 Mol. Wt.C7H4ClFO 158.56
1g5g
O
H
Cl
F
52,742-4 Mol. Wt.C7H5NO4 167.12
1g5g
O
H
OH
NO2
49,386-4 Mol. Wt.C7H6O4 154.12
1g
O
H
OHHO
HO
53,306-8 Mol. Wt.C7H7NO2 137.14
5g
N
O
H
O
52,918-4 Mol. Wt.C7H3F3O 160.10
1g5g
O
HF
F F
52,660-6 Mol. Wt.C7H4ClFO 158.56
1g5g
O
H
Cl
F
52,627-4 Mol. Wt.C7H5FO2 140.11
1g
O
H
OH
F
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
52,569-3 Mol. Wt.C6H4BrNO 186.01
1g10g
NBr
O
H
52,659-2 Mol. Wt.C7H3ClF2O 176.55
1g5g
O
H
Cl
F
F
51,830-1 Mol. Wt.C7H4FNO3 169.11
1g
O
H
NO2
F
51,677-5 Mol. Wt.C7H5BrO2 201.02
5g
O
H
Br
HO
52,887-0 Mol. Wt.C7H4BrFO 203.01
25g
O
HBr
F
52,663-0 Mol. Wt.C8H3ClF4O 226.56
1g5g
O
H
Cl
F
F3C
52,664-9 Mol. Wt.C8H3ClF4O 226.56
1g5g
O
H
Cl
F
CF3
52,897-8 Mol. Wt.C7H4BrFO 203.01
1g5g
O
HF
Br
52,921-4 Mol. Wt.C8H4F4O 192.10
1g5g
O
H
FF3C
52,914-1 Mol. Wt.C8H5F3OS 206.17
5g
O
H
SF3C
52,920-6 Mol. Wt.C8H4F4O 192.10
1g5g
O
HF3C
F
51,574-4 Mol. Wt.C8H6Br2O2 293.95
5g
O
H
O
Br
Br
52,916-8 Mol. Wt.C8H5F3O2 190.11
1g5g
O
H
O
CF3
52,922-2 Mol. Wt.C8H4F4O 192.10
1mL10mL
52,667-3 Mol. Wt.C11H8O2 172.18
1g5g
O
O
H
52,386-0 Mol. Wt.C11H12N2O 188.23
25g
O
H
N
CN
E540-9 Mol. Wt.C10H12O3 180.20
5g
O
H
O
O
51,804-2 Mol. Wt.C11H14O 162.23
5g
O
H
53,565-6 Mol. Wt.C11H8ClNO 205.64
1g
N
O
H
Cl
51,678-3 Mol. Wt.C11H14O3 194.23
5g
O
H
O
O
13,413-9 Mol. Wt.C10H9NO 159.19
1g5g
NH
O
H
53,564-8 Mol. Wt.C11H8ClNO 205.64
5g
N
O
H
Cl
51,630-9 Mol. Wt.C11H14O3 194.23
5g
O
H
OO
54,332-2 Mol. Wt.C15H11NO 221.26
1g5g
NH
O
H
51,112-9 Mol. Wt.C10H9NO 159.19
5g
N
O
H
49,399-6 Mol. Wt.C11H8ClNO2 221.65
5g
N
O
H
Cl
O
52,648-7 Mol. Wt.C12H10O 170.21
1g10g
OH
40,587-6 Mol. Wt.C15H12N2O2 252.27
1g5g
NNH
O
HO
52,645-2 Mol. Wt.C10H12O2 148.21
1g10g
O
H
51,640-6 Mol. Wt.C10H12O3 180.21
5g
53,308-4 Mol. Wt.C12H10O2 186.21
5g
O
H
O
49,974-9 Mol. Wt.C14H12O2 212.25
10mL50mL
O
H
O
52,338-0 Mol. Wt.C12H14OSi 202.33
5g
O
H
TMSi
54,981-9 Mol. Wt.C15H10FNO 239.24
1g5g
NH
O
H
F
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
49,387-2 Mol. Wt.C16H16O2 240.30
1g
O
H
O
51,577-9 Mol. Wt.C16H24O2 248.37
5g
O
H
O
52,665-7 Mol. Wt.C13H10O 182.22
5g
OH
54,333-0 Mol. Wt.C14H11BrO2 291.14
1g10g
O
H
O
Br
ArylaldehydesArylaldehydes
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
Arylaldehyde Resins for SPOS
Scavenger Resins5
for Aldehydes
References: (1) Wilson, T.W. et al. Tetrahedron Lett. 1997,38, 7151. (2) Sarantakis, D. et al. Tetrahedron Lett. 1997,38, 7325. (3) Bilodeau, M.T. et al. J. Org. Chem. 1998, 63,2800. (4) Estep, K.G. et al. J. Org. Chem. 1998, 63, 5300. (5) Kaldor, S.W. et al. Tetrahedron Lett. 1996, 40, 7193.
The following resins are useful for thesolid phase preparation of secondarysulfonamides, amides, ureas, and carbamates, and feature dilute-acid-labile linkers.1-4
Base resin
51,644-9AMEBA resin, 100-200 mesh, 1% cross-linked, 1.0-1.5 mmol/g
1g; 5g53,821-34-Benzyloxy-2,6-dimethoxybenz-aldehyde, polymer-bound, 100-200 mesh, 1% cross-linked
1g; 5g; 25g
51,627-93-Formyl-1-indoleacetic acid, polymer-bound
1g; 5g; 25g
53,240-1Formylpolystyrene, 100-200 mesh, 1% cross-linked, 0.7-1.5 mmol/g
1g; 5g; 25g
47,978-0Diethylenetriamine, polymer-bound, 2.5-3.0 mmol N/g
5g; 25g47,209-3Ethylenediamine, polymer-bound,1% cross-linked, 2.5-3.0 mmol N/g
5g; 25g
53,233-9p-Toluenesulfonyl hydrazide, polymer-bound, 1% cross-linked, 100-200 mesh, ~1.5 mmol N/g
1g; 5g; 25g
Please call us at 800-336-9719 (USA) or 314-534-4900, contact your localSigma-Aldrich office, or visit us at
www.sigma-aldrich.com/safc.
Sigma-Aldrich Fine Chemicals is readyto provide a competitive bulk quote
on any of our products includingthose listed in this publication.
✔ Prompt delivery of the broadestrange of chemicals from stock.
✔ Extensive custom processdevelopment and scaleup.
✔ New large scale & cGMP manufacturing facilities worldwide.
✔ Custom packaging.
✔ Analytical services & regulatory support.
We offer:
Name _____________________________________________________________
Company __________________________________________________________
Department____________________________ Mail Stop__________________
Address _______________________________________ Bldg/Rm # _________
City_______________ State____ Country___________ Postal Code________
Phone________________ Fax _________________ E-mail_________________
Tell Us About YourselfTell Us About Yourself
A reagent thatturns aldehydespurple!
Purpald®
References: (1) Hopps, H.B. Aldrichimica Acta 2000, 33, 28. (2) Dickinson, R.G.; Jacobsen, N.W. Chem Commun. 1970, 1719.Purpald is a registered trademark of Sigma-Aldrich Co.
O
H
F
F3C
O
H
O
O
H
O
O
The emerging importance of combinatorial and high-throughput methods in chemistryhas resulted in a need for specialized kits of chemicals. We are able to provide a variety of these kits by combining Aldrich’s vast chemical inventory and our customizedweighing process. Some of our more popular kits have included carboxylic acids, arylboronic acids, amines, and alcohols, and we are now pleased to add isocyanates tothis list. Please contact us. We can create a kit tailored to your specific requirements.
Key Features Include:Flexibility
❖ Ideal for high-throughput or combinatorial chemistry; available in vials or titerplates
No Minimum Order❖ Service as diverse as your needs
Reduces Waste❖ Little or no unused product to store or dispose
Saves Time❖ Less time weighing reagents, more time doing research
For more information on this unique service, please call us at800-333-7306 (USA) or e-mail us at [email protected].
In Europe, e-mail us at [email protected].
Aldrich Offers CombiKits™
CombiKits™ is a trademark of Sigma-Aldrich Co.
CGM
For a complete listing of all of our arylaldehydes, please visit our Web site at www.sigma-aldrich.com/aldrich, go to the Organics area, and click on Specialty Areas; or contact our Technical Services department by phone, 800-231-8327 (USA),
fax, 414-287-4079, or e-mail, [email protected]. As always, new product suggestions are welcome and appreciated.
Essential Tools for Today’s Synthetic Chemist
Arylaldehydes
54,264-4 Mol. Wt.C8H7FO2 154.14
1g5g
O
H
F
O
52,681-9 Mol. Wt.C8H7FO3 170.14
1g
O
HO
F
HO
51,513-2 Mol. Wt.C8H7FO 138.14
5g
O
H
F
51,832-8 Mol. Wt.C8H7NO3 165.15
1g
O
H
NO2
52,898-6 Mol. Wt.C8H7FO2 154.14
25g
O
H
O F
51,576-0 Mol. Wt.C8H7NO4 181.15
5g
O
H
O
O2N
52,662-2 Mol. Wt.C8H6ClFO 172.58
1g5g
O
H
F
Cl
53,673-3 Mol. Wt.C8H7FO2 154.14
1g5g
O
H
F
O
51,642-2 Mol. Wt.C8H7NO4 181.15
5g
O
H
O
NO2
51,383-0 Mol. Wt.C9H7NO 145.16
5g
NH
O
H
52,661-4 Mol. Wt.C8H6ClFO 172.58
1g5g
O
H
Cl
F
52,310-0 Mol. Wt.C8H7FO2 154.14
1g5g
O
H
O
F
52,311-9 Mol. Wt.C8H8OS 152.22
5g
O
H
S
52,306-2 Mol. Wt.C9H8O 132.16
5g
O
H
52,923-0 Mol. Wt.C8H6F2O2 172.12
5g
O
H
OCF2H
52,314-3 Mol. Wt.C8H7FO 138.14
5g
O
H
F
51,286-9 Mol. Wt.C8H9BO4 179.97
5g25g
O
H
B(OH)2
O
51,874-3 Mol. Wt.C9H6BrNO 224.06
5g
NH
O
HBr
34,854-6 Mol. Wt.C9H9FO3 184.16
1g
O
H
O
O
F
51,806-9 Mol. Wt.C9H10O 134.18
1g5g
O
H
51,805-0 Mol. Wt.
C9H10O 134.18
5g
O
H
52,640-1 Mol. Wt.C9H4F6O 242.12
1g5g
O
H
CF3F3C
53,307-6 Mol. Wt.C9H6ClNO 179.60
5g
NH
O
HCl
51,575-2 Mol. Wt.C9H9BrO2 229.08
5g
O
H
O
Br
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
51,515-9 Mol. Wt.C9H10O 134.18
5g
O
H
51,535-3 Mol. Wt.C9H10O 134.18
1g5g
O
H
49,385-6 Mol. Wt.C9H10O 134.18
1g5g
O
H
54,382-9 Mol. Wt.C10H4FNO5 237.14
1g
O
O
H
O
F
NO2
51,631-7 Mol. Wt.C9H10O2 150.18
1g5g
O
H
O
54,372-1 Mol. Wt.C10H6ClFO2 212.60
1g
O
O
H
Cl
F
54,362-4 Mol. Wt.C10H5FO3 192.15
1g
O
O
H
O
F
51,632-5 Mol. Wt.C9H10O2 150.18
5g
Arylaldehyde chemistry has led to a wealth of diverse products, so naturally Aldrich is determined to offer thewidest possible breadth of substitution patterns. Target molecules prepared from groups of arylaldehydes haveincluded aminoindenes,1 quinolines,2 arylglycines,3 and homoallylic alcohols.4 With over 400 arylaldehydes amongthe more than 80,000 products in stock at Sigma-Aldrich, chances are you’ll find what you’re looking for!
(1) Katritzky, A. R. et al. J. Org. Chem. 2000, 65, 8066. (2) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977. (3) Beller, M. et al. J. Org. Chem. 1998, 63,5658. (4) Curran, D.P.; Zhiyong, L. Med. Chem. Res. 1998, 8, 261. 1. What type of chemistry do you routinely perform?
❍ General Organic Chemistry [ORGS] ❍ Organometallics [ORGM]❍ Organic Combinatorial [COCH] ❍ Polymer Chemistry [POLY]❍ Chiral Chemistry [CHIR] ❍ Drug Discovery [DRUG]
2. Please check any of the following FREE catalog and literature piecesthat you would like to receive.❍ Aldrich Handbook [002]❍ Sigma General Catalog [001]❍ Fluka/Riedel-de-Haën® Catalog [003]❍ Aldrichimica Acta [032]❍ Resins for Combichem [DLW]❍ Combikits™/Small Sample Service [CBJ]❍ Polymer Products CD [DGQ]❍ New Fluorinated Products [DEO]❍ Products for Suzuki Coupling [DTK]
3. What other specialized grouping would be of interest to you?❍ Oxidizing agents [3AA] ❍ Terminal alkenes [3AE]❍ Reducing agents [3AB] ❍ Sulfonyl chlorides [3AF]❍ Oximes [3AC] ❍ Nitriles [3AG]❍ Terminal alkynes [3AD] ❍ Other _____________________
4. ❍ I would like to receive a FREE CD-ROM with product listingsfrom the Sigma-Aldrich Library of Rare Chemicals. [DDH]
Fluka/Riedel-de-Haën and Combikits are a registered trademark and trademark, respectively, of Sigma-Aldrich Co.
Purpald®, an aminotriazole, continues to be useful as a complexation reagent for the spectrophotomeric determination of aldehydes, e.g., in drug concentrationanalyses and in determining airborne formaldehyde.Ketones, esters, formic acid, amides, hydroxylamines,quinones, uric acid, hydrazines and aminophenols do not react with Purpald® to yield purple products.1-2
For properties, procedure for detecting aldehydes, applications, and references of Purpald®, please contact our Technical Services department at 800-231-8327(USA)or your local office and request Aldrich Technical Bulletin#AL-145; or visit our Web site, www.sigma-aldrich.com/aldrichand click on Technical Bulletins.
16,289-2 Purpald®, 99+%(4-amino-3-hydrazino-5-mercapto-1,2,4-triazole)
5g; 25g; 100g
53,145-6 Mol. Wt.C5H3ClO2 130.53
1g
OCl
O
H
49,990-0 Mol. Wt.C5H5BO3S 155.97
1g5g
S
O
H
B(OH)2
51,405-5 Mol. Wt.C5H5BO3S 155.97
1g5g
S(HO)2B
H
O
49,991-9 Mol. Wt.C5H5BO3S 155.97
1g5g
S
O
H
B(OH)2
52,642-8 Mol. Wt.C7H3ClF2O 176.55
1g5g
O
H
F
Cl
F
52,391-7 Mol. Wt.C7H4Cl2O 175.01
5g
O
H
Cl
Cl
52,919-2 Mol. Wt.C7H3F3O 160.10
1mL5mL
O
H
F
F
F
54,331-4 Mol. Wt.C7H4FIO 250.01
1g
O
H
F
I
52,917-6 Mol. Wt.C7H3F3O 160.10
5mL
O
H
F
F
F
53,724-1 Mol. Wt.C7H4ClFO 158.56
1g5g
O
H
Cl
F
52,742-4 Mol. Wt.C7H5NO4 167.12
1g5g
O
H
OH
NO2
49,386-4 Mol. Wt.C7H6O4 154.12
1g
O
H
OHHO
HO
53,306-8 Mol. Wt.C7H7NO2 137.14
5g
N
O
H
O
52,918-4 Mol. Wt.C7H3F3O 160.10
1g5g
O
HF
F F
52,660-6 Mol. Wt.C7H4ClFO 158.56
1g5g
O
H
Cl
F
52,627-4 Mol. Wt.C7H5FO2 140.11
1g
O
H
OH
F
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
52,569-3 Mol. Wt.C6H4BrNO 186.01
1g10g
NBr
O
H
52,659-2 Mol. Wt.C7H3ClF2O 176.55
1g5g
O
H
Cl
F
F
51,830-1 Mol. Wt.C7H4FNO3 169.11
1g
O
H
NO2
F
51,677-5 Mol. Wt.C7H5BrO2 201.02
5g
O
H
Br
HO
52,887-0 Mol. Wt.C7H4BrFO 203.01
25g
O
HBr
F
52,663-0 Mol. Wt.C8H3ClF4O 226.56
1g5g
O
H
Cl
F
F3C
52,664-9 Mol. Wt.C8H3ClF4O 226.56
1g5g
O
H
Cl
F
CF3
52,897-8 Mol. Wt.C7H4BrFO 203.01
1g5g
O
HF
Br
52,921-4 Mol. Wt.C8H4F4O 192.10
1g5g
O
H
FF3C
52,914-1 Mol. Wt.C8H5F3OS 206.17
5g
O
H
SF3C
52,920-6 Mol. Wt.C8H4F4O 192.10
1g5g
O
HF3C
F
51,574-4 Mol. Wt.C8H6Br2O2 293.95
5g
O
H
O
Br
Br
52,916-8 Mol. Wt.C8H5F3O2 190.11
1g5g
O
H
O
CF3
52,922-2 Mol. Wt.C8H4F4O 192.10
1mL10mL
52,667-3 Mol. Wt.C11H8O2 172.18
1g5g
O
O
H
52,386-0 Mol. Wt.C11H12N2O 188.23
25g
O
H
N
CN
E540-9 Mol. Wt.C10H12O3 180.20
5g
O
H
O
O
51,804-2 Mol. Wt.C11H14O 162.23
5g
O
H
53,565-6 Mol. Wt.C11H8ClNO 205.64
1g
N
O
H
Cl
51,678-3 Mol. Wt.C11H14O3 194.23
5g
O
H
O
O
13,413-9 Mol. Wt.C10H9NO 159.19
1g5g
NH
O
H
53,564-8 Mol. Wt.C11H8ClNO 205.64
5g
N
O
H
Cl
51,630-9 Mol. Wt.C11H14O3 194.23
5g
O
H
OO
54,332-2 Mol. Wt.C15H11NO 221.26
1g5g
NH
O
H
51,112-9 Mol. Wt.C10H9NO 159.19
5g
N
O
H
49,399-6 Mol. Wt.C11H8ClNO2 221.65
5g
N
O
H
Cl
O
52,648-7 Mol. Wt.C12H10O 170.21
1g10g
OH
40,587-6 Mol. Wt.C15H12N2O2 252.27
1g5g
NNH
O
HO
52,645-2 Mol. Wt.C10H12O2 148.21
1g10g
O
H
51,640-6 Mol. Wt.C10H12O3 180.21
5g
53,308-4 Mol. Wt.C12H10O2 186.21
5g
O
H
O
49,974-9 Mol. Wt.C14H12O2 212.25
10mL50mL
O
H
O
52,338-0 Mol. Wt.C12H14OSi 202.33
5g
O
H
TMSi
54,981-9 Mol. Wt.C15H10FNO 239.24
1g5g
NH
O
H
F
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
49,387-2 Mol. Wt.C16H16O2 240.30
1g
O
H
O
51,577-9 Mol. Wt.C16H24O2 248.37
5g
O
H
O
52,665-7 Mol. Wt.C13H10O 182.22
5g
OH
54,333-0 Mol. Wt.C14H11BrO2 291.14
1g10g
O
H
O
Br
ArylaldehydesArylaldehydes
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
Arylaldehyde Resins for SPOS
Scavenger Resins5
for Aldehydes
References: (1) Wilson, T.W. et al. Tetrahedron Lett. 1997,38, 7151. (2) Sarantakis, D. et al. Tetrahedron Lett. 1997,38, 7325. (3) Bilodeau, M.T. et al. J. Org. Chem. 1998, 63,2800. (4) Estep, K.G. et al. J. Org. Chem. 1998, 63, 5300. (5) Kaldor, S.W. et al. Tetrahedron Lett. 1996, 40, 7193.
The following resins are useful for thesolid phase preparation of secondarysulfonamides, amides, ureas, and carbamates, and feature dilute-acid-labile linkers.1-4
Base resin
51,644-9AMEBA resin, 100-200 mesh, 1% cross-linked, 1.0-1.5 mmol/g
1g; 5g53,821-34-Benzyloxy-2,6-dimethoxybenz-aldehyde, polymer-bound, 100-200 mesh, 1% cross-linked
1g; 5g; 25g
51,627-93-Formyl-1-indoleacetic acid, polymer-bound
1g; 5g; 25g
53,240-1Formylpolystyrene, 100-200 mesh, 1% cross-linked, 0.7-1.5 mmol/g
1g; 5g; 25g
47,978-0Diethylenetriamine, polymer-bound, 2.5-3.0 mmol N/g
5g; 25g47,209-3Ethylenediamine, polymer-bound,1% cross-linked, 2.5-3.0 mmol N/g
5g; 25g
53,233-9p-Toluenesulfonyl hydrazide, polymer-bound, 1% cross-linked, 100-200 mesh, ~1.5 mmol N/g
1g; 5g; 25g
Please call us at 800-336-9719 (USA) or 314-534-4900, contact your localSigma-Aldrich office, or visit us at
www.sigma-aldrich.com/safc.
Sigma-Aldrich Fine Chemicals is readyto provide a competitive bulk quote
on any of our products includingthose listed in this publication.
✔ Prompt delivery of the broadestrange of chemicals from stock.
✔ Extensive custom processdevelopment and scaleup.
✔ New large scale & cGMP manufacturing facilities worldwide.
✔ Custom packaging.
✔ Analytical services & regulatory support.
We offer:
Name _____________________________________________________________
Company __________________________________________________________
Department____________________________ Mail Stop__________________
Address _______________________________________ Bldg/Rm # _________
City_______________ State____ Country___________ Postal Code________
Phone________________ Fax _________________ E-mail_________________
Tell Us About YourselfTell Us About Yourself
A reagent thatturns aldehydespurple!
Purpald®
References: (1) Hopps, H.B. Aldrichimica Acta 2000, 33, 28. (2) Dickinson, R.G.; Jacobsen, N.W. Chem Commun. 1970, 1719.Purpald is a registered trademark of Sigma-Aldrich Co.
O
H
F
F3C
O
H
O
O
H
O
O
The emerging importance of combinatorial and high-throughput methods in chemistryhas resulted in a need for specialized kits of chemicals. We are able to provide a variety of these kits by combining Aldrich’s vast chemical inventory and our customizedweighing process. Some of our more popular kits have included carboxylic acids, arylboronic acids, amines, and alcohols, and we are now pleased to add isocyanates tothis list. Please contact us. We can create a kit tailored to your specific requirements.
Key Features Include:Flexibility
❖ Ideal for high-throughput or combinatorial chemistry; available in vials or titerplates
No Minimum Order❖ Service as diverse as your needs
Reduces Waste❖ Little or no unused product to store or dispose
Saves Time❖ Less time weighing reagents, more time doing research
For more information on this unique service, please call us at800-333-7306 (USA) or e-mail us at [email protected].
In Europe, e-mail us at [email protected].
Aldrich Offers CombiKits™
CombiKits™ is a trademark of Sigma-Aldrich Co.
CGM
For a complete listing of all of our arylaldehydes, please visit our Web site at www.sigma-aldrich.com/aldrich, go to the Organics area, and click on Specialty Areas; or contact our Technical Services department by phone, 800-231-8327 (USA),
fax, 414-287-4079, or e-mail, [email protected]. As always, new product suggestions are welcome and appreciated.
Essential Tools for Today’s Synthetic Chemist
Arylaldehydes
54,264-4 Mol. Wt.C8H7FO2 154.14
1g5g
O
H
F
O
52,681-9 Mol. Wt.C8H7FO3 170.14
1g
O
HO
F
HO
51,513-2 Mol. Wt.C8H7FO 138.14
5g
O
H
F
51,832-8 Mol. Wt.C8H7NO3 165.15
1g
O
H
NO2
52,898-6 Mol. Wt.C8H7FO2 154.14
25g
O
H
O F
51,576-0 Mol. Wt.C8H7NO4 181.15
5g
O
H
O
O2N
52,662-2 Mol. Wt.C8H6ClFO 172.58
1g5g
O
H
F
Cl
53,673-3 Mol. Wt.C8H7FO2 154.14
1g5g
O
H
F
O
51,642-2 Mol. Wt.C8H7NO4 181.15
5g
O
H
O
NO2
51,383-0 Mol. Wt.C9H7NO 145.16
5g
NH
O
H
52,661-4 Mol. Wt.C8H6ClFO 172.58
1g5g
O
H
Cl
F
52,310-0 Mol. Wt.C8H7FO2 154.14
1g5g
O
H
O
F
52,311-9 Mol. Wt.C8H8OS 152.22
5g
O
H
S
52,306-2 Mol. Wt.C9H8O 132.16
5g
O
H
52,923-0 Mol. Wt.C8H6F2O2 172.12
5g
O
H
OCF2H
52,314-3 Mol. Wt.C8H7FO 138.14
5g
O
H
F
51,286-9 Mol. Wt.C8H9BO4 179.97
5g25g
O
H
B(OH)2
O
51,874-3 Mol. Wt.C9H6BrNO 224.06
5g
NH
O
HBr
34,854-6 Mol. Wt.C9H9FO3 184.16
1g
O
H
O
O
F
51,806-9 Mol. Wt.C9H10O 134.18
1g5g
O
H
51,805-0 Mol. Wt.
C9H10O 134.18
5g
O
H
52,640-1 Mol. Wt.C9H4F6O 242.12
1g5g
O
H
CF3F3C
53,307-6 Mol. Wt.C9H6ClNO 179.60
5g
NH
O
HCl
51,575-2 Mol. Wt.C9H9BrO2 229.08
5g
O
H
O
Br
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
51,515-9 Mol. Wt.C9H10O 134.18
5g
O
H
51,535-3 Mol. Wt.C9H10O 134.18
1g5g
O
H
49,385-6 Mol. Wt.C9H10O 134.18
1g5g
O
H
54,382-9 Mol. Wt.C10H4FNO5 237.14
1g
O
O
H
O
F
NO2
51,631-7 Mol. Wt.C9H10O2 150.18
1g5g
O
H
O
54,372-1 Mol. Wt.C10H6ClFO2 212.60
1g
O
O
H
Cl
F
54,362-4 Mol. Wt.C10H5FO3 192.15
1g
O
O
H
O
F
51,632-5 Mol. Wt.C9H10O2 150.18
5g
Arylaldehyde chemistry has led to a wealth of diverse products, so naturally Aldrich is determined to offer thewidest possible breadth of substitution patterns. Target molecules prepared from groups of arylaldehydes haveincluded aminoindenes,1 quinolines,2 arylglycines,3 and homoallylic alcohols.4 With over 400 arylaldehydes amongthe more than 80,000 products in stock at Sigma-Aldrich, chances are you’ll find what you’re looking for!
(1) Katritzky, A. R. et al. J. Org. Chem. 2000, 65, 8066. (2) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977. (3) Beller, M. et al. J. Org. Chem. 1998, 63,5658. (4) Curran, D.P.; Zhiyong, L. Med. Chem. Res. 1998, 8, 261. 1. What type of chemistry do you routinely perform?
❍ General Organic Chemistry [ORGS] ❍ Organometallics [ORGM]❍ Organic Combinatorial [COCH] ❍ Polymer Chemistry [POLY]❍ Chiral Chemistry [CHIR] ❍ Drug Discovery [DRUG]
2. Please check any of the following FREE catalog and literature piecesthat you would like to receive.❍ Aldrich Handbook [002]❍ Sigma General Catalog [001]❍ Fluka/Riedel-de-Haën® Catalog [003]❍ Aldrichimica Acta [032]❍ Resins for Combichem [DLW]❍ Combikits™/Small Sample Service [CBJ]❍ Polymer Products CD [DGQ]❍ New Fluorinated Products [DEO]❍ Products for Suzuki Coupling [DTK]
3. What other specialized grouping would be of interest to you?❍ Oxidizing agents [3AA] ❍ Terminal alkenes [3AE]❍ Reducing agents [3AB] ❍ Sulfonyl chlorides [3AF]❍ Oximes [3AC] ❍ Nitriles [3AG]❍ Terminal alkynes [3AD] ❍ Other _____________________
4. ❍ I would like to receive a FREE CD-ROM with product listingsfrom the Sigma-Aldrich Library of Rare Chemicals. [DDH]
Fluka/Riedel-de-Haën and Combikits are a registered trademark and trademark, respectively, of Sigma-Aldrich Co.
Purpald®, an aminotriazole, continues to be useful as a complexation reagent for the spectrophotomeric determination of aldehydes, e.g., in drug concentrationanalyses and in determining airborne formaldehyde.Ketones, esters, formic acid, amides, hydroxylamines,quinones, uric acid, hydrazines and aminophenols do not react with Purpald® to yield purple products.1-2
For properties, procedure for detecting aldehydes, applications, and references of Purpald®, please contact our Technical Services department at 800-231-8327(USA)or your local office and request Aldrich Technical Bulletin#AL-145; or visit our Web site, www.sigma-aldrich.com/aldrichand click on Technical Bulletins.
16,289-2 Purpald®, 99+%(4-amino-3-hydrazino-5-mercapto-1,2,4-triazole)
5g; 25g; 100g
53,145-6 Mol. Wt.C5H3ClO2 130.53
1g
OCl
O
H
49,990-0 Mol. Wt.C5H5BO3S 155.97
1g5g
S
O
H
B(OH)2
51,405-5 Mol. Wt.C5H5BO3S 155.97
1g5g
S(HO)2B
H
O
49,991-9 Mol. Wt.C5H5BO3S 155.97
1g5g
S
O
H
B(OH)2
52,642-8 Mol. Wt.C7H3ClF2O 176.55
1g5g
O
H
F
Cl
F
52,391-7 Mol. Wt.C7H4Cl2O 175.01
5g
O
H
Cl
Cl
52,919-2 Mol. Wt.C7H3F3O 160.10
1mL5mL
O
H
F
F
F
54,331-4 Mol. Wt.C7H4FIO 250.01
1g
O
H
F
I
52,917-6 Mol. Wt.C7H3F3O 160.10
5mL
O
H
F
F
F
53,724-1 Mol. Wt.C7H4ClFO 158.56
1g5g
O
H
Cl
F
52,742-4 Mol. Wt.C7H5NO4 167.12
1g5g
O
H
OH
NO2
49,386-4 Mol. Wt.C7H6O4 154.12
1g
O
H
OHHO
HO
53,306-8 Mol. Wt.C7H7NO2 137.14
5g
N
O
H
O
52,918-4 Mol. Wt.C7H3F3O 160.10
1g5g
O
HF
F F
52,660-6 Mol. Wt.C7H4ClFO 158.56
1g5g
O
H
Cl
F
52,627-4 Mol. Wt.C7H5FO2 140.11
1g
O
H
OH
F
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
52,569-3 Mol. Wt.C6H4BrNO 186.01
1g10g
NBr
O
H
52,659-2 Mol. Wt.C7H3ClF2O 176.55
1g5g
O
H
Cl
F
F
51,830-1 Mol. Wt.C7H4FNO3 169.11
1g
O
H
NO2
F
51,677-5 Mol. Wt.C7H5BrO2 201.02
5g
O
H
Br
HO
52,887-0 Mol. Wt.C7H4BrFO 203.01
25g
O
HBr
F
52,663-0 Mol. Wt.C8H3ClF4O 226.56
1g5g
O
H
Cl
F
F3C
52,664-9 Mol. Wt.C8H3ClF4O 226.56
1g5g
O
H
Cl
F
CF3
52,897-8 Mol. Wt.C7H4BrFO 203.01
1g5g
O
HF
Br
52,921-4 Mol. Wt.C8H4F4O 192.10
1g5g
O
H
FF3C
52,914-1 Mol. Wt.C8H5F3OS 206.17
5g
O
H
SF3C
52,920-6 Mol. Wt.C8H4F4O 192.10
1g5g
O
HF3C
F
51,574-4 Mol. Wt.C8H6Br2O2 293.95
5g
O
H
O
Br
Br
52,916-8 Mol. Wt.C8H5F3O2 190.11
1g5g
O
H
O
CF3
52,922-2 Mol. Wt.C8H4F4O 192.10
1mL10mL
52,667-3 Mol. Wt.C11H8O2 172.18
1g5g
O
O
H
52,386-0 Mol. Wt.C11H12N2O 188.23
25g
O
H
N
CN
E540-9 Mol. Wt.C10H12O3 180.20
5g
O
H
O
O
51,804-2 Mol. Wt.C11H14O 162.23
5g
O
H
53,565-6 Mol. Wt.C11H8ClNO 205.64
1g
N
O
H
Cl
51,678-3 Mol. Wt.C11H14O3 194.23
5g
O
H
O
O
13,413-9 Mol. Wt.C10H9NO 159.19
1g5g
NH
O
H
53,564-8 Mol. Wt.C11H8ClNO 205.64
5g
N
O
H
Cl
51,630-9 Mol. Wt.C11H14O3 194.23
5g
O
H
OO
54,332-2 Mol. Wt.C15H11NO 221.26
1g5g
NH
O
H
51,112-9 Mol. Wt.C10H9NO 159.19
5g
N
O
H
49,399-6 Mol. Wt.C11H8ClNO2 221.65
5g
N
O
H
Cl
O
52,648-7 Mol. Wt.C12H10O 170.21
1g10g
OH
40,587-6 Mol. Wt.C15H12N2O2 252.27
1g5g
NNH
O
HO
52,645-2 Mol. Wt.C10H12O2 148.21
1g10g
O
H
51,640-6 Mol. Wt.C10H12O3 180.21
5g
53,308-4 Mol. Wt.C12H10O2 186.21
5g
O
H
O
49,974-9 Mol. Wt.C14H12O2 212.25
10mL50mL
O
H
O
52,338-0 Mol. Wt.C12H14OSi 202.33
5g
O
H
TMSi
54,981-9 Mol. Wt.C15H10FNO 239.24
1g5g
NH
O
H
F
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
49,387-2 Mol. Wt.C16H16O2 240.30
1g
O
H
O
51,577-9 Mol. Wt.C16H24O2 248.37
5g
O
H
O
52,665-7 Mol. Wt.C13H10O 182.22
5g
OH
54,333-0 Mol. Wt.C14H11BrO2 291.14
1g10g
O
H
O
Br
ArylaldehydesArylaldehydes
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
Arylaldehyde Resins for SPOS
Scavenger Resins5
for Aldehydes
References: (1) Wilson, T.W. et al. Tetrahedron Lett. 1997,38, 7151. (2) Sarantakis, D. et al. Tetrahedron Lett. 1997,38, 7325. (3) Bilodeau, M.T. et al. J. Org. Chem. 1998, 63,2800. (4) Estep, K.G. et al. J. Org. Chem. 1998, 63, 5300. (5) Kaldor, S.W. et al. Tetrahedron Lett. 1996, 40, 7193.
The following resins are useful for thesolid phase preparation of secondarysulfonamides, amides, ureas, and carbamates, and feature dilute-acid-labile linkers.1-4
Base resin
51,644-9AMEBA resin, 100-200 mesh, 1% cross-linked, 1.0-1.5 mmol/g
1g; 5g53,821-34-Benzyloxy-2,6-dimethoxybenz-aldehyde, polymer-bound, 100-200 mesh, 1% cross-linked
1g; 5g; 25g
51,627-93-Formyl-1-indoleacetic acid, polymer-bound
1g; 5g; 25g
53,240-1Formylpolystyrene, 100-200 mesh, 1% cross-linked, 0.7-1.5 mmol/g
1g; 5g; 25g
47,978-0Diethylenetriamine, polymer-bound, 2.5-3.0 mmol N/g
5g; 25g47,209-3Ethylenediamine, polymer-bound,1% cross-linked, 2.5-3.0 mmol N/g
5g; 25g
53,233-9p-Toluenesulfonyl hydrazide, polymer-bound, 1% cross-linked, 100-200 mesh, ~1.5 mmol N/g
1g; 5g; 25g
Please call us at 800-336-9719 (USA) or 314-534-4900, contact your localSigma-Aldrich office, or visit us at
www.sigma-aldrich.com/safc.
Sigma-Aldrich Fine Chemicals is readyto provide a competitive bulk quote
on any of our products includingthose listed in this publication.
✔ Prompt delivery of the broadestrange of chemicals from stock.
✔ Extensive custom processdevelopment and scaleup.
✔ New large scale & cGMP manufacturing facilities worldwide.
✔ Custom packaging.
✔ Analytical services & regulatory support.
We offer:
Name _____________________________________________________________
Company __________________________________________________________
Department____________________________ Mail Stop__________________
Address _______________________________________ Bldg/Rm # _________
City_______________ State____ Country___________ Postal Code________
Phone________________ Fax _________________ E-mail_________________
Tell Us About YourselfTell Us About Yourself
A reagent thatturns aldehydespurple!
Purpald®
References: (1) Hopps, H.B. Aldrichimica Acta 2000, 33, 28. (2) Dickinson, R.G.; Jacobsen, N.W. Chem Commun. 1970, 1719.Purpald is a registered trademark of Sigma-Aldrich Co.
O
H
F
F3C
O
H
O
O
H
O
O
The emerging importance of combinatorial and high-throughput methods in chemistryhas resulted in a need for specialized kits of chemicals. We are able to provide a variety of these kits by combining Aldrich’s vast chemical inventory and our customizedweighing process. Some of our more popular kits have included carboxylic acids, arylboronic acids, amines, and alcohols, and we are now pleased to add isocyanates tothis list. Please contact us. We can create a kit tailored to your specific requirements.
Key Features Include:Flexibility
❖ Ideal for high-throughput or combinatorial chemistry; available in vials or titerplates
No Minimum Order❖ Service as diverse as your needs
Reduces Waste❖ Little or no unused product to store or dispose
Saves Time❖ Less time weighing reagents, more time doing research
For more information on this unique service, please call us at800-333-7306 (USA) or e-mail us at [email protected].
In Europe, e-mail us at [email protected].
Aldrich Offers CombiKits™
CombiKits™ is a trademark of Sigma-Aldrich Co.
CGM
For a complete listing of all of our arylaldehydes, please visit our Web site at www.sigma-aldrich.com/aldrich, go to the Organics area, and click on Specialty Areas; or contact our Technical Services department by phone, 800-231-8327 (USA),
fax, 414-287-4079, or e-mail, [email protected]. As always, new product suggestions are welcome and appreciated.
Essential Tools for Today’s Synthetic Chemist
Arylaldehydes
54,264-4 Mol. Wt.C8H7FO2 154.14
1g5g
O
H
F
O
52,681-9 Mol. Wt.C8H7FO3 170.14
1g
O
HO
F
HO
51,513-2 Mol. Wt.C8H7FO 138.14
5g
O
H
F
51,832-8 Mol. Wt.C8H7NO3 165.15
1g
O
H
NO2
52,898-6 Mol. Wt.C8H7FO2 154.14
25g
O
H
O F
51,576-0 Mol. Wt.C8H7NO4 181.15
5g
O
H
O
O2N
52,662-2 Mol. Wt.C8H6ClFO 172.58
1g5g
O
H
F
Cl
53,673-3 Mol. Wt.C8H7FO2 154.14
1g5g
O
H
F
O
51,642-2 Mol. Wt.C8H7NO4 181.15
5g
O
H
O
NO2
51,383-0 Mol. Wt.C9H7NO 145.16
5g
NH
O
H
52,661-4 Mol. Wt.C8H6ClFO 172.58
1g5g
O
H
Cl
F
52,310-0 Mol. Wt.C8H7FO2 154.14
1g5g
O
H
O
F
52,311-9 Mol. Wt.C8H8OS 152.22
5g
O
H
S
52,306-2 Mol. Wt.C9H8O 132.16
5g
O
H
52,923-0 Mol. Wt.C8H6F2O2 172.12
5g
O
H
OCF2H
52,314-3 Mol. Wt.C8H7FO 138.14
5g
O
H
F
51,286-9 Mol. Wt.C8H9BO4 179.97
5g25g
O
H
B(OH)2
O
51,874-3 Mol. Wt.C9H6BrNO 224.06
5g
NH
O
HBr
34,854-6 Mol. Wt.C9H9FO3 184.16
1g
O
H
O
O
F
51,806-9 Mol. Wt.C9H10O 134.18
1g5g
O
H
51,805-0 Mol. Wt.
C9H10O 134.18
5g
O
H
52,640-1 Mol. Wt.C9H4F6O 242.12
1g5g
O
H
CF3F3C
53,307-6 Mol. Wt.C9H6ClNO 179.60
5g
NH
O
HCl
51,575-2 Mol. Wt.C9H9BrO2 229.08
5g
O
H
O
Br
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
51,515-9 Mol. Wt.C9H10O 134.18
5g
O
H
51,535-3 Mol. Wt.C9H10O 134.18
1g5g
O
H
49,385-6 Mol. Wt.C9H10O 134.18
1g5g
O
H
54,382-9 Mol. Wt.C10H4FNO5 237.14
1g
O
O
H
O
F
NO2
51,631-7 Mol. Wt.C9H10O2 150.18
1g5g
O
H
O
54,372-1 Mol. Wt.C10H6ClFO2 212.60
1g
O
O
H
Cl
F
54,362-4 Mol. Wt.C10H5FO3 192.15
1g
O
O
H
O
F
51,632-5 Mol. Wt.C9H10O2 150.18
5g
Arylaldehyde chemistry has led to a wealth of diverse products, so naturally Aldrich is determined to offer thewidest possible breadth of substitution patterns. Target molecules prepared from groups of arylaldehydes haveincluded aminoindenes,1 quinolines,2 arylglycines,3 and homoallylic alcohols.4 With over 400 arylaldehydes amongthe more than 80,000 products in stock at Sigma-Aldrich, chances are you’ll find what you’re looking for!
(1) Katritzky, A. R. et al. J. Org. Chem. 2000, 65, 8066. (2) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977. (3) Beller, M. et al. J. Org. Chem. 1998, 63,5658. (4) Curran, D.P.; Zhiyong, L. Med. Chem. Res. 1998, 8, 261. 1. What type of chemistry do you routinely perform?
❍ General Organic Chemistry [ORGS] ❍ Organometallics [ORGM]❍ Organic Combinatorial [COCH] ❍ Polymer Chemistry [POLY]❍ Chiral Chemistry [CHIR] ❍ Drug Discovery [DRUG]
2. Please check any of the following FREE catalog and literature piecesthat you would like to receive.❍ Aldrich Handbook [002]❍ Sigma General Catalog [001]❍ Fluka/Riedel-de-Haën® Catalog [003]❍ Aldrichimica Acta [032]❍ Resins for Combichem [DLW]❍ Combikits™/Small Sample Service [CBJ]❍ Polymer Products CD [DGQ]❍ New Fluorinated Products [DEO]❍ Products for Suzuki Coupling [DTK]
3. What other specialized grouping would be of interest to you?❍ Oxidizing agents [3AA] ❍ Terminal alkenes [3AE]❍ Reducing agents [3AB] ❍ Sulfonyl chlorides [3AF]❍ Oximes [3AC] ❍ Nitriles [3AG]❍ Terminal alkynes [3AD] ❍ Other _____________________
4. ❍ I would like to receive a FREE CD-ROM with product listingsfrom the Sigma-Aldrich Library of Rare Chemicals. [DDH]
Fluka/Riedel-de-Haën and Combikits are a registered trademark and trademark, respectively, of Sigma-Aldrich Co.
Purpald®, an aminotriazole, continues to be useful as a complexation reagent for the spectrophotomeric determination of aldehydes, e.g., in drug concentrationanalyses and in determining airborne formaldehyde.Ketones, esters, formic acid, amides, hydroxylamines,quinones, uric acid, hydrazines and aminophenols do not react with Purpald® to yield purple products.1-2
For properties, procedure for detecting aldehydes, applications, and references of Purpald®, please contact our Technical Services department at 800-231-8327(USA)or your local office and request Aldrich Technical Bulletin#AL-145; or visit our Web site, www.sigma-aldrich.com/aldrichand click on Technical Bulletins.
16,289-2 Purpald®, 99+%(4-amino-3-hydrazino-5-mercapto-1,2,4-triazole)
5g; 25g; 100g
53,145-6 Mol. Wt.C5H3ClO2 130.53
1g
OCl
O
H
49,990-0 Mol. Wt.C5H5BO3S 155.97
1g5g
S
O
H
B(OH)2
51,405-5 Mol. Wt.C5H5BO3S 155.97
1g5g
S(HO)2B
H
O
49,991-9 Mol. Wt.C5H5BO3S 155.97
1g5g
S
O
H
B(OH)2
52,642-8 Mol. Wt.C7H3ClF2O 176.55
1g5g
O
H
F
Cl
F
52,391-7 Mol. Wt.C7H4Cl2O 175.01
5g
O
H
Cl
Cl
52,919-2 Mol. Wt.C7H3F3O 160.10
1mL5mL
O
H
F
F
F
54,331-4 Mol. Wt.C7H4FIO 250.01
1g
O
H
F
I
52,917-6 Mol. Wt.C7H3F3O 160.10
5mL
O
H
F
F
F
53,724-1 Mol. Wt.C7H4ClFO 158.56
1g5g
O
H
Cl
F
52,742-4 Mol. Wt.C7H5NO4 167.12
1g5g
O
H
OH
NO2
49,386-4 Mol. Wt.C7H6O4 154.12
1g
O
H
OHHO
HO
53,306-8 Mol. Wt.C7H7NO2 137.14
5g
N
O
H
O
52,918-4 Mol. Wt.C7H3F3O 160.10
1g5g
O
HF
F F
52,660-6 Mol. Wt.C7H4ClFO 158.56
1g5g
O
H
Cl
F
52,627-4 Mol. Wt.C7H5FO2 140.11
1g
O
H
OH
F
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
52,569-3 Mol. Wt.C6H4BrNO 186.01
1g10g
NBr
O
H
52,659-2 Mol. Wt.C7H3ClF2O 176.55
1g5g
O
H
Cl
F
F
51,830-1 Mol. Wt.C7H4FNO3 169.11
1g
O
H
NO2
F
51,677-5 Mol. Wt.C7H5BrO2 201.02
5g
O
H
Br
HO
52,887-0 Mol. Wt.C7H4BrFO 203.01
25g
O
HBr
F
52,663-0 Mol. Wt.C8H3ClF4O 226.56
1g5g
O
H
Cl
F
F3C
52,664-9 Mol. Wt.C8H3ClF4O 226.56
1g5g
O
H
Cl
F
CF3
52,897-8 Mol. Wt.C7H4BrFO 203.01
1g5g
O
HF
Br
52,921-4 Mol. Wt.C8H4F4O 192.10
1g5g
O
H
FF3C
52,914-1 Mol. Wt.C8H5F3OS 206.17
5g
O
H
SF3C
52,920-6 Mol. Wt.C8H4F4O 192.10
1g5g
O
HF3C
F
51,574-4 Mol. Wt.C8H6Br2O2 293.95
5g
O
H
O
Br
Br
52,916-8 Mol. Wt.C8H5F3O2 190.11
1g5g
O
H
O
CF3
52,922-2 Mol. Wt.C8H4F4O 192.10
1mL10mL
52,667-3 Mol. Wt.C11H8O2 172.18
1g5g
O
O
H
52,386-0 Mol. Wt.C11H12N2O 188.23
25g
O
H
N
CN
E540-9 Mol. Wt.C10H12O3 180.20
5g
O
H
O
O
51,804-2 Mol. Wt.C11H14O 162.23
5g
O
H
53,565-6 Mol. Wt.C11H8ClNO 205.64
1g
N
O
H
Cl
51,678-3 Mol. Wt.C11H14O3 194.23
5g
O
H
O
O
13,413-9 Mol. Wt.C10H9NO 159.19
1g5g
NH
O
H
53,564-8 Mol. Wt.C11H8ClNO 205.64
5g
N
O
H
Cl
51,630-9 Mol. Wt.C11H14O3 194.23
5g
O
H
OO
54,332-2 Mol. Wt.C15H11NO 221.26
1g5g
NH
O
H
51,112-9 Mol. Wt.C10H9NO 159.19
5g
N
O
H
49,399-6 Mol. Wt.C11H8ClNO2 221.65
5g
N
O
H
Cl
O
52,648-7 Mol. Wt.C12H10O 170.21
1g10g
OH
40,587-6 Mol. Wt.C15H12N2O2 252.27
1g5g
NNH
O
HO
52,645-2 Mol. Wt.C10H12O2 148.21
1g10g
O
H
51,640-6 Mol. Wt.C10H12O3 180.21
5g
53,308-4 Mol. Wt.C12H10O2 186.21
5g
O
H
O
49,974-9 Mol. Wt.C14H12O2 212.25
10mL50mL
O
H
O
52,338-0 Mol. Wt.C12H14OSi 202.33
5g
O
H
TMSi
54,981-9 Mol. Wt.C15H10FNO 239.24
1g5g
NH
O
H
F
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
49,387-2 Mol. Wt.C16H16O2 240.30
1g
O
H
O
51,577-9 Mol. Wt.C16H24O2 248.37
5g
O
H
O
52,665-7 Mol. Wt.C13H10O 182.22
5g
OH
54,333-0 Mol. Wt.C14H11BrO2 291.14
1g10g
O
H
O
Br
ArylaldehydesArylaldehydes
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com
Arylaldehyde Resins for SPOS
Scavenger Resins5
for Aldehydes
References: (1) Wilson, T.W. et al. Tetrahedron Lett. 1997,38, 7151. (2) Sarantakis, D. et al. Tetrahedron Lett. 1997,38, 7325. (3) Bilodeau, M.T. et al. J. Org. Chem. 1998, 63,2800. (4) Estep, K.G. et al. J. Org. Chem. 1998, 63, 5300. (5) Kaldor, S.W. et al. Tetrahedron Lett. 1996, 40, 7193.
The following resins are useful for thesolid phase preparation of secondarysulfonamides, amides, ureas, and carbamates, and feature dilute-acid-labile linkers.1-4
Base resin
51,644-9AMEBA resin, 100-200 mesh, 1% cross-linked, 1.0-1.5 mmol/g
1g; 5g53,821-34-Benzyloxy-2,6-dimethoxybenz-aldehyde, polymer-bound, 100-200 mesh, 1% cross-linked
1g; 5g; 25g
51,627-93-Formyl-1-indoleacetic acid, polymer-bound
1g; 5g; 25g
53,240-1Formylpolystyrene, 100-200 mesh, 1% cross-linked, 0.7-1.5 mmol/g
1g; 5g; 25g
47,978-0Diethylenetriamine, polymer-bound, 2.5-3.0 mmol N/g
5g; 25g47,209-3Ethylenediamine, polymer-bound,1% cross-linked, 2.5-3.0 mmol N/g
5g; 25g
53,233-9p-Toluenesulfonyl hydrazide, polymer-bound, 1% cross-linked, 100-200 mesh, ~1.5 mmol N/g
1g; 5g; 25g
Please call us at 800-336-9719 (USA) or 314-534-4900, contact your localSigma-Aldrich office, or visit us at
www.sigma-aldrich.com/safc.
Sigma-Aldrich Fine Chemicals is readyto provide a competitive bulk quote
on any of our products includingthose listed in this publication.
✔ Prompt delivery of the broadestrange of chemicals from stock.
✔ Extensive custom processdevelopment and scaleup.
✔ New large scale & cGMP manufacturing facilities worldwide.
✔ Custom packaging.
✔ Analytical services & regulatory support.
We offer:
Name _____________________________________________________________
Company __________________________________________________________
Department____________________________ Mail Stop__________________
Address _______________________________________ Bldg/Rm # _________
City_______________ State____ Country___________ Postal Code________
Phone________________ Fax _________________ E-mail_________________
Tell Us About YourselfTell Us About Yourself
A reagent thatturns aldehydespurple!
Purpald®
References: (1) Hopps, H.B. Aldrichimica Acta 2000, 33, 28. (2) Dickinson, R.G.; Jacobsen, N.W. Chem Commun. 1970, 1719.Purpald is a registered trademark of Sigma-Aldrich Co.
O
H
F
F3C
O
H
O
O
H
O
O
The emerging importance of combinatorial and high-throughput methods in chemistryhas resulted in a need for specialized kits of chemicals. We are able to provide a variety of these kits by combining Aldrich’s vast chemical inventory and our customizedweighing process. Some of our more popular kits have included carboxylic acids, arylboronic acids, amines, and alcohols, and we are now pleased to add isocyanates tothis list. Please contact us. We can create a kit tailored to your specific requirements.
Key Features Include:Flexibility
❖ Ideal for high-throughput or combinatorial chemistry; available in vials or titerplates
No Minimum Order❖ Service as diverse as your needs
Reduces Waste❖ Little or no unused product to store or dispose
Saves Time❖ Less time weighing reagents, more time doing research
For more information on this unique service, please call us at800-333-7306 (USA) or e-mail us at [email protected].
In Europe, e-mail us at [email protected].
Aldrich Offers CombiKits™
CombiKits™ is a trademark of Sigma-Aldrich Co.
CGM
For a complete listing of all of our arylaldehydes, please visit our Web site at www.sigma-aldrich.com/aldrich, go to the Organics area, and click on Specialty Areas; or contact our Technical Services department by phone, 800-231-8327 (USA),
fax, 414-287-4079, or e-mail, [email protected]. As always, new product suggestions are welcome and appreciated.
Essential Tools for Today’s Synthetic Chemist
NO
PO
STA
GE
NE
CE
SS
AR
Y IF
MA
ILED
IN T
HE
UN
ITE
D S
TATE
S
BU
SIN
ES
S R
EP
LY M
AIL
FIR
ST
-CLA
SS
MA
IL PE
RM
IT N
O.3038 S
T.LOU
IS, M
O
PO
STA
GE
WILL B
E PA
ID B
Y A
DD
RE
SS
EE
SIG
MA
P.O.B
OX
14508S
T.LOU
IS, M
O, U
SA
63178-9916
NewArylaldehydes
Global Bulk
Manufacturing
❖
Combikits™
(Vials or
Titerplates)
❖
Arylaldehyde
Resins
for SPOS
❖
Over 80 New
Products!
Organic SynthesisBuilding Blocks for
TO ORDER
PHONE
FAX
800-558-9160 (USA)or 414-273-3850
800-962-9591 (USA)or 414-273-4979
Aldrich Chemical CompanyP.O. Box 2060Milwaukee, WI 53201
ArgentinaSigma-Aldrich de Argentina, S.ATel: 54 11 4807 0321Fax: 54 11 4807 0346E-mail: [email protected]
AustraliaSigma-Aldrich Pty., LimitedFree Tel: 1-800-800-097Free Fax: 1-800-800-096Tel: 61-2-9841-0555Fax: 61-2-9841-0500E-mail: [email protected]
AustriaSigma-Aldrich Handels GmbHTel: 43 1 605 8110Fax: 43 1 605 8120E-mail: [email protected]
BelgiumSigma-Aldrich nv/saFree Tel: 0800-147.47Free Fax: 0800-147.45Tel: 03 899.13.01Fax: 03 899.13.11E-mail: [email protected]
BrazilSigma-Aldrich Química Brasil Ltda.Tel: 55-11-231-1866Fax: 55-11-257-9079E-mail: [email protected]
CanadaSigma-Aldrich Canada Ltd.Free Tel: 800-565-1400Free Fax: 800-265-3858Tel: 905-829-9500Fax: 905-829-9292E-mail: [email protected]
Czech RepublicSigma-Aldrich s.r.o.Tel: 00-420-2-2176 1300Fax: 00-420-2-2176 3300E-mail:[email protected]
DenmarkSigma-Aldrich Denmark A/STel: +45 43 56 59 10Fax: +45 43 56 59 05E-mail: [email protected]
EireSigma-Aldrich Ireland Ltd.Free Tel: 1 800 200 888Free Fax: 1 800 600 222Tel: 01 404 1900Fax: 01 404 1910E-mail: [email protected]
FinlandSigma-Aldrich FinlandTel: (09) 350-9250Fax: (09) 350-92555E-mail: [email protected]
FranceSigma-Aldrich Chimie S.a.r.lTel Numero Vert: 0800 21 14 08Fax Numero Vert: 0800 03 10 52E-mail: [email protected]
Germany(also SE Europe, the Baltics, Africa and theMiddle East)Sigma-Aldrich Chemie GmbHFreecall Tel: 0800-5155 000Freecall Fax: 0800-6490 000Tel: +49(0)89-6513-0Fax: +49(0)89-6513-1169E-mail: [email protected] Slovakia, Africa, Middle East and other European countries:Tel: +49(0)89-6513-1807Fax: +49(0)89-6513-1877
GreeceSigma-Aldrich (o.m) Ltd.Tel: 30-1-9948010Fax: 30-1-9943831E-mail: [email protected]
HungarySigma-Aldrich KftTel: 06-1-269-6474Fax: 06-1-235-9050E-mail: [email protected]
IndiaSigma-Aldrich CorporationBangalore location:Phone: 91 80 851 8797Fax: 91 80 851 8358
New Delhi location:Phone: (011) 689 9826Fax: (011) 689 9827E-mail: [email protected]
IsraelSigma Israel Chemicals Ltd.Toll Free Tel: 1-800-70-2222Tel: 972-8-948-4222Fax: 972-8-948-4200E-mail: [email protected]
ItalySigma-Aldrich S.r.l.Numero Verde: 800-827018Tel: 02-33417.310Fax: 02-38010.737E-mail: [email protected]
JapanSigma-Aldrich Japan K.K.Tel: 81-3-5821-3111Fax: 81-3-5821-3170
KoreaSigma-Aldrich KoreaToll Free Tel: 080-023-7111Toll Free Fax: 080-023-8111Tel: 82-2-783-5211Fax: 82-2-783-5011E-mail: [email protected]
MalaysiaSigma-Aldrich (M) Sdn BhdTel: 03-7824181, 03-7808140Fax: 03-7824067E-mail: [email protected]
MexicoSigma-Aldrich Química, S.A. de C.V.Tel Gratis: 91-800-0075300Tel: (72) 76 1600Fax: (72) 76 1601E-mail: [email protected]
NetherlandsSigma-Aldrich Chemie BVTel Gratis: 0800 022 9088Fax Gratis: 0800 022 9089Tel: 078-620 54 11Fax: 078-620 54 21E-mail: [email protected]
NorwaySigma-Aldrich Norway ASTel: 47 23 176 000Fax: 47 23 176 010E-mail: [email protected]
PolandSigma-Aldrich Sp.zo.oTel: (48-61) 823-24-81Fax: (48-61) 823-27-81E-mail: [email protected]
PortugalSigma-Aldrich Quimica S.A.Free Tel: 0800-202180Free Fax: 0800-202178E-mail, encomendas:[email protected]
RussiaSigma-Aldrich RussiaTel: 7-095-975-3321Fax: 7-095-975-4792E-mail: [email protected]
SingaporeSigma-Aldrich Pte., Ltd.Tel: (65) 271 1089Fax: (65) 271 1571E-mail: [email protected]
South AfricaSigma-Aldrich South Africa (Pty) Ltd.Tel: (011) 397 8886Fax: (011) 397 8859E-mail: [email protected]
SpainSigma-Aldrich Química S.A.Free Tel: 900-101376Free Fax: 900-102028Tel: 91-6619977Fax: 91-6619642E-mail, pedidos:[email protected]
SwedenSigma-Aldrich Sweden ABTel: 020-35 05 10Fax: 020-35 25 22Outside Sweden Tel: 46-8-742 4200Outside Sweden Fax: 46-8-742 4243E-mail: [email protected]
SwitzerlandAldrich ChemieA division of Fluka Chemie AGTel: 081-755 27 23Fax: 081-755 28 40Swiss Free Call: 0800 80 00 80E-mail: [email protected]
United KingdomSigma-Aldrich Company Ltd.Free Tel: 0800 717181Free Fax: 0800 378538Tel: 01202 733114Fax: 01202 715460E-mail: [email protected]
United StatesAldrich Chemical Company, Inc.Toll Free Tel: 1-800-558-9160Toll Free Fax: 1-800-962-9591Tel: 414-273-3850Fax: 414-273-4979E-mail: [email protected]
Sigma Chemical CompanyToll Free Tel: 1-800-521-8956Toll Free Fax: 1-800-325-5052Tel: 314-771-5765Fax: 314-771-5757E-mail: [email protected]
© 2000 Sigma-Aldrich Co. Printed in USA. Aldrich brand products are sold through Sigma-Aldrich, Inc. Sigma-Aldrich, Inc. warrants that its products conform to the information contained in thisand other Sigma-Aldrich publications. Purchaser must determine the suitability of the product(s) for their particular use. Additional terms and conditions may apply. Please see reverse side of theinvoice or packing slip. Aldrich is a registered trademark of Sigma-Aldrich. Riedel-de Haën®: trademark under license from Riedel-de Haën GmbH.
World Headquarters: 1001 W. St. Paul Ave., Milwaukee,WI 53233 USA • (001) 414-273-3850 • www.sigma-aldrich.com
Biochemicals and Reagents for Life Science Research
Specialty Chemicalsand Analytical
Reagents for Research
Laboratory Chemicalsand Reagents for
Research and Analysis
Chromatography Products for Analysis
and Purification
Organics and Inorganics for
Chemical Synthesis
The SIGMA-ALDRICHFamily
DUG
For Development/Manufacturing Quantities For Quantity Pricing/Standing OrdersContact your local Sigma-Aldrich office Contact your local Sigma-Aldrich officeand ask for Sigma-Aldrich Fine Chemicals
P.O. Box 355Milwaukee, WI 53201USA
Return Service Requested
Sigma-Aldrich Worldwide Locations
Mas
terc
ard
, Vis
a, a
nd
Am
eric
an E
xpre
ss a
ccep
ted
. N
O m
inim
um
ord
er O
R c
on
firm
ing
pu
rch
ase
ord
er r
equ
ired
.
ChemFiles Vol. 1, No. 2 • 2001Dess–Martin Periodinane
is widely used for the mild
oxidation of alcohols to
aldehydes and ketones.1
This reagent is especially useful
for substrates containing sensitive
functional groups and offers an
alternative to other mild
reagents (e.g. TPAP). Other
advantages such as selectivity,
rapid rates, avoiding the use of
toxic (i.e. chromium-based)
chemicals, using stoichiometric
amounts of reagent, and ease of
work up make the Dess–Martin
periodinane a reliable and easy-to-
use oxidizer in organic synthesis.
Dess–Martin PeriodinaneDess–Martin Periodinane
1. Useful in the preparation of epimerization-sensitive optically active N-protected α-amino aldehydes with high enantiomeric excess.2
2. Oximes and tosylhydrazones are converted to their corresponding carbonyl compounds under mild conditionswithout overoxidation of the final product.3
3. Oxidation of sugar hydroxyls in good yields with periodinane avoids the use of ruthenium dioxide.4
4. A highly unstable dialdehyde was prepared by oxidation with periodinane and trapped in situ with a pre-formed Wittig ylide.5
5. A convenient route to the preparation of highly reactive acyl nitroso compounds. These products can be trapped by dienes to form cycloadducts.6
6. Rapid production of complex and diverse natural product-like polycycles. A proposed mechanism starts with an ortho-oxidation followed by an intramolecular hetero Diels–Alder reaction.7
7. Neutral and mild work-up conditions avoid the formation of dehydrofluorinated by-products in the oxidation of polyfluorinated primary alcohols to aldehydes.8
27,462-3 Dess-Martin periodinane, 97% 1g; 5g[1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one]
Preparation of ArylaldehydesPreparation of ArylaldehydesVarious routes are available for the formation of arylaldehydes, including classical aromatic formylation viaVilsmeier, Gatterman, or Reimer–Tiemann reactions. Other methods include reduction of carboxylic acid derivatives,especially the reduction of esters with DIBAH9, and the oxidation of alcohols, typically with chromium reagents but accomplished under mild conditions with TPAP10 or Dess-Martin periodinane (see above).
33,074-4 Tetrapropylammonium perruthenate, 97% (TPAP) 250mg; 1g25,681-1 Diisobutylaluminum hydride (DIBAH) 100g; 1kg19,014-4 Pyridinium chlorochromate, 98% (PCC) 25g; 100g; 500g21,469-8 Pyridinium dichromate, 98% (PDC) 5g; 100g 500g
References: (1) Dess, D.B; Martin, J. C. J. Org. Chem. 1983, 48, 4155. (2) Myers, A.G. et al. Tetrahedron Lett. 2000, 41, 1359. (3) Bose, D.S.; Narsaiah, A. V. Synth. Commun.1999, 29, 937. (4) Rao, H. S. P. et al. Indian J. Chem., Sect. B. 1997, 36B, 816. (5) Barrett, A. G.M. et al. J. Org. Chem. 1997, 62, 9376. (6) Jenkins, N. E. et al. Synth. Commun.2000, 30, 947. (7) Nicolaou, K.C. et al. Angew. Chem., Int. Ed. Engl. 2000, 39, 622. (8) Lévêque, L. et al. Tetrahedron Lett. 1998. 39, 8857. (9) Winterfeldt, E. Synthesis1975, 617. (10) Ley, S.V. et al. ibid. 1994, 639.
NO
PO
STA
GE
NE
CE
SS
AR
Y IF
MA
ILED
IN T
HE
UN
ITE
D S
TATE
S
BU
SIN
ES
S R
EP
LY M
AIL
FIR
ST
-CLA
SS
MA
IL PE
RM
IT N
O.3038 S
T.LOU
IS, M
O
PO
STA
GE
WILL B
E PA
ID B
Y A
DD
RE
SS
EE
SIG
MA
P.O.B
OX
14508S
T.LOU
IS, M
O, U
SA
63178-9916
NewArylaldehydes
Global Bulk
Manufacturing
❖
Combikits™
(Vials or
Titerplates)
❖
Arylaldehyde
Resins
for SPOS
❖
Over 80 New
Products!
Organic SynthesisBuilding Blocks for
TO ORDER
PHONE
FAX
800-558-9160 (USA)or 414-273-3850
800-962-9591 (USA)or 414-273-4979
Aldrich Chemical CompanyP.O. Box 2060Milwaukee, WI 53201
ArgentinaSigma-Aldrich de Argentina, S.ATel: 54 11 4807 0321Fax: 54 11 4807 0346E-mail: [email protected]
AustraliaSigma-Aldrich Pty., LimitedFree Tel: 1-800-800-097Free Fax: 1-800-800-096Tel: 61-2-9841-0555Fax: 61-2-9841-0500E-mail: [email protected]
AustriaSigma-Aldrich Handels GmbHTel: 43 1 605 8110Fax: 43 1 605 8120E-mail: [email protected]
BelgiumSigma-Aldrich nv/saFree Tel: 0800-147.47Free Fax: 0800-147.45Tel: 03 899.13.01Fax: 03 899.13.11E-mail: [email protected]
BrazilSigma-Aldrich Química Brasil Ltda.Tel: 55-11-231-1866Fax: 55-11-257-9079E-mail: [email protected]
CanadaSigma-Aldrich Canada Ltd.Free Tel: 800-565-1400Free Fax: 800-265-3858Tel: 905-829-9500Fax: 905-829-9292E-mail: [email protected]
Czech RepublicSigma-Aldrich s.r.o.Tel: 00-420-2-2176 1300Fax: 00-420-2-2176 3300E-mail:[email protected]
DenmarkSigma-Aldrich Denmark A/STel: +45 43 56 59 10Fax: +45 43 56 59 05E-mail: [email protected]
EireSigma-Aldrich Ireland Ltd.Free Tel: 1 800 200 888Free Fax: 1 800 600 222Tel: 01 404 1900Fax: 01 404 1910E-mail: [email protected]
FinlandSigma-Aldrich FinlandTel: (09) 350-9250Fax: (09) 350-92555E-mail: [email protected]
FranceSigma-Aldrich Chimie S.a.r.lTel Numero Vert: 0800 21 14 08Fax Numero Vert: 0800 03 10 52E-mail: [email protected]
Germany(also SE Europe, the Baltics, Africa and theMiddle East)Sigma-Aldrich Chemie GmbHFreecall Tel: 0800-5155 000Freecall Fax: 0800-6490 000Tel: +49(0)89-6513-0Fax: +49(0)89-6513-1169E-mail: [email protected] Slovakia, Africa, Middle East and other European countries:Tel: +49(0)89-6513-1807Fax: +49(0)89-6513-1877
GreeceSigma-Aldrich (o.m) Ltd.Tel: 30-1-9948010Fax: 30-1-9943831E-mail: [email protected]
HungarySigma-Aldrich KftTel: 06-1-269-6474Fax: 06-1-235-9050E-mail: [email protected]
IndiaSigma-Aldrich CorporationBangalore location:Phone: 91 80 851 8797Fax: 91 80 851 8358
New Delhi location:Phone: (011) 689 9826Fax: (011) 689 9827E-mail: [email protected]
IsraelSigma Israel Chemicals Ltd.Toll Free Tel: 1-800-70-2222Tel: 972-8-948-4222Fax: 972-8-948-4200E-mail: [email protected]
ItalySigma-Aldrich S.r.l.Numero Verde: 800-827018Tel: 02-33417.310Fax: 02-38010.737E-mail: [email protected]
JapanSigma-Aldrich Japan K.K.Tel: 81-3-5821-3111Fax: 81-3-5821-3170
KoreaSigma-Aldrich KoreaToll Free Tel: 080-023-7111Toll Free Fax: 080-023-8111Tel: 82-2-783-5211Fax: 82-2-783-5011E-mail: [email protected]
MalaysiaSigma-Aldrich (M) Sdn BhdTel: 03-7824181, 03-7808140Fax: 03-7824067E-mail: [email protected]
MexicoSigma-Aldrich Química, S.A. de C.V.Tel Gratis: 91-800-0075300Tel: (72) 76 1600Fax: (72) 76 1601E-mail: [email protected]
NetherlandsSigma-Aldrich Chemie BVTel Gratis: 0800 022 9088Fax Gratis: 0800 022 9089Tel: 078-620 54 11Fax: 078-620 54 21E-mail: [email protected]
NorwaySigma-Aldrich Norway ASTel: 47 23 176 000Fax: 47 23 176 010E-mail: [email protected]
PolandSigma-Aldrich Sp.zo.oTel: (48-61) 823-24-81Fax: (48-61) 823-27-81E-mail: [email protected]
PortugalSigma-Aldrich Quimica S.A.Free Tel: 0800-202180Free Fax: 0800-202178E-mail, encomendas:[email protected]
RussiaSigma-Aldrich RussiaTel: 7-095-975-3321Fax: 7-095-975-4792E-mail: [email protected]
SingaporeSigma-Aldrich Pte., Ltd.Tel: (65) 271 1089Fax: (65) 271 1571E-mail: [email protected]
South AfricaSigma-Aldrich South Africa (Pty) Ltd.Tel: (011) 397 8886Fax: (011) 397 8859E-mail: [email protected]
SpainSigma-Aldrich Química S.A.Free Tel: 900-101376Free Fax: 900-102028Tel: 91-6619977Fax: 91-6619642E-mail, pedidos:[email protected]
SwedenSigma-Aldrich Sweden ABTel: 020-35 05 10Fax: 020-35 25 22Outside Sweden Tel: 46-8-742 4200Outside Sweden Fax: 46-8-742 4243E-mail: [email protected]
SwitzerlandAldrich ChemieA division of Fluka Chemie AGTel: 081-755 27 23Fax: 081-755 28 40Swiss Free Call: 0800 80 00 80E-mail: [email protected]
United KingdomSigma-Aldrich Company Ltd.Free Tel: 0800 717181Free Fax: 0800 378538Tel: 01202 733114Fax: 01202 715460E-mail: [email protected]
United StatesAldrich Chemical Company, Inc.Toll Free Tel: 1-800-558-9160Toll Free Fax: 1-800-962-9591Tel: 414-273-3850Fax: 414-273-4979E-mail: [email protected]
Sigma Chemical CompanyToll Free Tel: 1-800-521-8956Toll Free Fax: 1-800-325-5052Tel: 314-771-5765Fax: 314-771-5757E-mail: [email protected]
© 2000 Sigma-Aldrich Co. Printed in USA. Aldrich brand products are sold through Sigma-Aldrich, Inc. Sigma-Aldrich, Inc. warrants that its products conform to the information contained in thisand other Sigma-Aldrich publications. Purchaser must determine the suitability of the product(s) for their particular use. Additional terms and conditions may apply. Please see reverse side of theinvoice or packing slip. Aldrich is a registered trademark of Sigma-Aldrich. Riedel-de Haën®: trademark under license from Riedel-de Haën GmbH.
World Headquarters: 1001 W. St. Paul Ave., Milwaukee,WI 53233 USA • (001) 414-273-3850 • www.sigma-aldrich.com
Biochemicals and Reagents for Life Science Research
Specialty Chemicalsand Analytical
Reagents for Research
Laboratory Chemicalsand Reagents for
Research and Analysis
Chromatography Products for Analysis
and Purification
Organics and Inorganics for
Chemical Synthesis
The SIGMA-ALDRICHFamily
DUG
For Development/Manufacturing Quantities For Quantity Pricing/Standing OrdersContact your local Sigma-Aldrich office Contact your local Sigma-Aldrich officeand ask for Sigma-Aldrich Fine Chemicals
P.O. Box 355Milwaukee, WI 53201USA
Return Service Requested
Sigma-Aldrich Worldwide Locations
Mas
terc
ard
, Vis
a, a
nd
Am
eric
an E
xpre
ss a
ccep
ted
. N
O m
inim
um
ord
er O
R c
on
firm
ing
pu
rch
ase
ord
er r
equ
ired
.
ChemFiles Vol. 1, No. 2 • 2001Dess–Martin Periodinane
is widely used for the mild
oxidation of alcohols to
aldehydes and ketones.1
This reagent is especially useful
for substrates containing sensitive
functional groups and offers an
alternative to other mild
reagents (e.g. TPAP). Other
advantages such as selectivity,
rapid rates, avoiding the use of
toxic (i.e. chromium-based)
chemicals, using stoichiometric
amounts of reagent, and ease of
work up make the Dess–Martin
periodinane a reliable and easy-to-
use oxidizer in organic synthesis.
Dess–Martin PeriodinaneDess–Martin Periodinane
1. Useful in the preparation of epimerization-sensitive optically active N-protected α-amino aldehydes with high enantiomeric excess.2
2. Oximes and tosylhydrazones are converted to their corresponding carbonyl compounds under mild conditionswithout overoxidation of the final product.3
3. Oxidation of sugar hydroxyls in good yields with periodinane avoids the use of ruthenium dioxide.4
4. A highly unstable dialdehyde was prepared by oxidation with periodinane and trapped in situ with a pre-formed Wittig ylide.5
5. A convenient route to the preparation of highly reactive acyl nitroso compounds. These products can be trapped by dienes to form cycloadducts.6
6. Rapid production of complex and diverse natural product-like polycycles. A proposed mechanism starts with an ortho-oxidation followed by an intramolecular hetero Diels–Alder reaction.7
7. Neutral and mild work-up conditions avoid the formation of dehydrofluorinated by-products in the oxidation of polyfluorinated primary alcohols to aldehydes.8
27,462-3 Dess-Martin periodinane, 97% 1g; 5g[1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one]
Preparation of ArylaldehydesPreparation of ArylaldehydesVarious routes are available for the formation of arylaldehydes, including classical aromatic formylation viaVilsmeier, Gatterman, or Reimer–Tiemann reactions. Other methods include reduction of carboxylic acid derivatives,especially the reduction of esters with DIBAH9, and the oxidation of alcohols, typically with chromium reagents but accomplished under mild conditions with TPAP10 or Dess-Martin periodinane (see above).
33,074-4 Tetrapropylammonium perruthenate, 97% (TPAP) 250mg; 1g25,681-1 Diisobutylaluminum hydride (DIBAH) 100g; 1kg19,014-4 Pyridinium chlorochromate, 98% (PCC) 25g; 100g; 500g21,469-8 Pyridinium dichromate, 98% (PDC) 5g; 100g 500g
References: (1) Dess, D.B; Martin, J. C. J. Org. Chem. 1983, 48, 4155. (2) Myers, A.G. et al. Tetrahedron Lett. 2000, 41, 1359. (3) Bose, D.S.; Narsaiah, A. V. Synth. Commun.1999, 29, 937. (4) Rao, H. S. P. et al. Indian J. Chem., Sect. B. 1997, 36B, 816. (5) Barrett, A. G.M. et al. J. Org. Chem. 1997, 62, 9376. (6) Jenkins, N. E. et al. Synth. Commun.2000, 30, 947. (7) Nicolaou, K.C. et al. Angew. Chem., Int. Ed. Engl. 2000, 39, 622. (8) Lévêque, L. et al. Tetrahedron Lett. 1998. 39, 8857. (9) Winterfeldt, E. Synthesis1975, 617. (10) Ley, S.V. et al. ibid. 1994, 639.