Saltar al contenido
MilliporeSigma
Todas las fotos(2)

Key Documents

View All Documentation

513210

Sigma-Aldrich

(S)-(−)-2-Methyl-2-propanesulfinamide

97%

Sinónimos:

(S)-(-)-tert-Butanesulfinamide, (S)-(-)-tert-Butyl sulfinamide, (S)-2-Methyl-2-propanesulfinamide, (S)-tert-Butanesulfinamide, (S)-tert-Butylsulfinamide

Iniciar sesiónpara Ver la Fijación de precios por contrato y de la organización
Todas las fotos(2)

About This Item

Fórmula lineal:
(CH3)3CS(O)NH2
Número de CAS:
343338-28-3
Peso molecular:
121.20
MDL number:
MFCD05861480
UNSPSC Code:
12352111
PubChem Substance ID:
24873681
NACRES:
NA.22

Quality Level

100

assay

97%

optical activity

[α]20/D −4.5°, c = 1 in chloroform

mp

97-101 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)(C)S(N)=O

InChI

1S/C4H11NOS/c1-4(2,3)7(5)6/h5H2,1-3H3/t7-/m0/s1

InChI key

CESUXLKAADQNTB-ZETCQYMHSA-N

Application

Ellman′s Sulfinamides
(S)-(-)-2-Methyl-2-propanesulfinamide may be used to develop benzofuran-based farnesyltransferase inhibitors as anti-cancer agents. It may also be used to prepare (20E)-N-[t-butyl-(S)-sulfinyl]-3β-(t-butyldimethylsilyloxy)-pregn-5-en-20-imine, an intermediate for the preparation of androgen receptor antagonists.
Can be readily transformed into P,N-sulfinyl imine ligands through condensation with aldehydes and ketones, which can undergo iridium-catalyzed asymmetric hydrogenation of olefins.
Chiral auxiliary used in an asymmetric preparation of trifluoroethylamines by conversion of trifluoroacetaldehyde to a chiral imine followed by treatment with an aryl lithium and acidic methanolysis.
Useful reagent for synthesizing chiral amines.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Elija entre una de las versiones más recientes:

Certificados de análisis (COA)

Lot/Batch Number
MKCQ1917
MKCK8329
MKCC8950
MKCB1775V
MKBZ2676V

¿No ve la versión correcta?

Si necesita una versión concreta, puede buscar un certificado específico por el número de lote.

Busque por un COA

¿Ya tiene este producto?

Encuentre la documentación para los productos que ha comprado recientemente en la Biblioteca de documentos.

Visite la Librería de documentos

Vouy Linh Truong et al.
Organic letters, 9(4), 683-685 (2007-01-30)
Condensation of N-tert-butanesulfinamide (S)-1 with trifluoroacetaldehyde hydrate 2a afforded 2-methyl-N-(2,2,2-trifluoroethylidene)propane-2-sulfinamide 3. Without isolation and purification, imine 3 was added to various aryllithium reagents to give highly diastereomerically enriched adducts 5a-g. Acidic methanolysis of 5a-g provided the desired 1-aryl-2,2,2-trifluoroethylamine hydrochloride compounds
20-Aminosteroids as a novel class of selective and complete androgen receptor antagonists and inhibitors of prostate cancer cell growth.
Fousteris MA, et al.
Bioorganic & Medicinal Chemistry Letters, 18(19), 6960-6969 (2010)
Synthesis and structure-activity relationships of novel benzofuran farnesyltransferase inhibitors.
Asoh K, et al.
Bioorganic & Medicinal Chemistry Letters, 19(6), 1753-1757 (2009)
Organic Letters, 69, 1800-1800 (2004)
Jonathan A Ellman et al.
Accounts of chemical research, 35(11), 984-995 (2002-11-20)
N-tert-Butanesulfinyl aldimines 3 and ketimines 4 are exceedingly versatile intermediates for the asymmetric synthesis of amines. The N-tert-butanesulfinyl imines are prepared in high yields by condensing enantiomerically pure tert-butanesulfinamide 1, which is readily available in either configuration, with a wide
Ver todos los artículos relacionados

Artículos

Ellman's Sulfinamides

Ellman's sulfinamide is available in both enantiomeric and racemic forms for your research. This versatile and useful auxiliary has found extensive use both in academics and industry.

Contenido relacionado

Ellman Group – Professor Product Portal

The Ellman group has participated in the development of a variety of C-H functionalization methods. An electron rich phosphine ligand has proven to be very useful for a variety of Rh(I)-catalyzed C-C bond forming reactions applicable to heterocycle synthesis as exemplified in the recent Science paper “Proton Donor Acidity Controls Selectivity in Nonaromatic Nitrogen Heterocycle Synthesis.” Another useful ligand developed for the highly functional group compatible direct arylation of nitrogen heterocycles is described in a 2008 J. Am. Chem. Soc. paper “Rh(I)-Catalyzed Arylation of Heterocycles via C-H Bond Activation: Expanded Scope through Mechanistic Insight.” The Ellman group also developed the chiral amine reagent tert-Butanesulfinamide, which is extensively used in academics and industry for the asymmetric synthesis of amines. A comprehensive survey of tert-Butanesulfinamide methods and applications up through 2009 is provided in the 2010 Chemical Reviews article, “Synthesis and Applications of tert-Butanesulfinamide.”

Nuestro equipo de científicos tiene experiencia en todas las áreas de investigación: Ciencias de la vida, Ciencia de los materiales, Síntesis química, Cromatografía, Analítica y muchas otras.

Póngase en contacto con el Servicio técnico