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
• 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

Properties

• Quality Level: 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

Description

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.

Safety Information

• 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