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497401

(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
NACRES:
NA.22
PubChem Substance ID:
24873117
UNSPSC Code:
12352111
MDL number:
MFCD05861479
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Quality Segment

100

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

General description

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

Application

(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 β-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.
Ellman′s Sulfinamides

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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