513210

Sigma-Aldrich

(S)-(−)-2-Methyl-2-propanesulfinamide

97%

Linear Formula:
(CH3)3CS(O)NH2
CAS Number:
Molecular Weight:
121.20
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

Useful reagent for synthesizing chiral amines.
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.
(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.

Packaging

1, 5, 25 g in glass bottle

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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)
Journal of the American Chemical Society, 119, 9913-9914 (1997)
Jeffrey P McMahon et al.
Organic letters, 6(10), 1645-1647 (2004-05-07)
Addition of alkyl or aryl Grignard reagents to N-sulfinyl imines derived from 3- and 4-substituted cyclohexanones proceeds with good yields and with excellent diasteroselectivity. The selectivity of the reaction is controlled by the ring substituent rather than the sulfinyl group...
Articles
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.
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Related Content
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.”
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