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497401

Sigma-Aldrich

(R)-(+)-2-Methyl-2-propanesulfinamide

98%

Synonym(s):

(R)-2-methyl-2-propanesulfinamide, (R)-2-methylpropane-2-sulfinamide, (R)-tert-butanesulfinamide, (R)-tert-butylsulfinamide

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About This Item

Linear Formula:
(CH3)3CS(O)NH2
CAS Number:
196929-78-9
Molecular Weight:
121.20
MDL number:
MFCD05861479
UNSPSC Code:
12352111
PubChem Substance ID:
24873117
NACRES:
NA.22

Assay

98%

optical activity

[α]20/D +4°, c = 1.0242 in chloroform stab. with amylenes

mp

103-107 °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-/m1/s1

InChI key

CESUXLKAADQNTB-SSDOTTSWSA-N

Related Categories

General description

(R)-(+)-2-Methyl-2-propanesulfinamide is a chiral auxiliary used in the condensation of the aldehyde.

Application

Ellman′s Sulfinamides
(R)-(+)-2-Methyl-2-propanesulfinamide may be used to prepare N-(1-cyclohexylmethylidene)-2-methylpropane-2-sulfinamide via copper mediated condensation with cyclohexane carboxaldehyde. It may also be used to prepare (20E)-N-[t-butyl-(R)-sulfinyl]-3β-(t-butyldimethylsilyloxy)-pregn-5-en-20-imine, an intermediate for the development 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.
Preparation of ß-chloro sulfinamides in a synthesis of chiral azridines. Also used to prepare an organocatalyst for enantioselective reduction of imines.
Useful reagent for synthesizing chiral amines.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW1907
MKCT9317
MKCT2204
MKCR4737
MKCN8525

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Bram Denolf et al.
Organic letters, 8(14), 3129-3132 (2006-06-30)
[reaction: see text] Reaction of chiral alpha-chloro tert-butanesulfinyl aldimines with Grignard reagents efficiently afforded beta-chloro N-sulfinamides in high diastereomeric excess. The latter compounds were cyclized toward the corresponding chiral aziridines in a high-yielding one-pot reaction or after separate treatment with
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, 18(19), 6960-6969 (2010)
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
Asymmetric synthesis of a, a-difluoro-?-amino acid derivatives from enantiomerically pure N-tert-butylsulfinimines.
Staas, DD, et al.
The Journal of Organic Chemistry, 67(23), 8276-8279 (2002)
Dong Pei et al.
Organic letters, 8(25), 5913-5915 (2006-12-01)
Easily accessible chiral sulfinamide 2 has been developed as the first highly efficient and enantioselective organocatalyst relying solely on a chiral sulfur center for stereochemical induction. In the presence of 20 mol % of 2, a broad range of N-aryl
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