(S)-2-methylpropane-2-sulfinamide

• ChemBase ID: 67396
• Molecular Formular: C4H11NOS
• Molecular Mass: 121.20124
• Monoisotopic Mass: 121.05613498
• SMILES: CC(C)([S@](=O)N)C
• Canonical SMILES: CC([S@](=O)N)(C)C
• InChI: InChI=1S/C4H11NOS/c1-4(2,3)7(5)6/h5H2,1-3H3/t7-/m0/s1
• InChIKey: CESUXLKAADQNTB-ZETCQYMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (S)-2-methylpropane-2-sulfinamide; (R)-2-methylpropane-2-sulfinamide; 2-methylpropane-2-sulfinamide
• IUPAC Traditional name: (S)-2-methylpropane-2-sulfinamide; (R)-2-methylpropane-2-sulfinamide
• Synonyms: (S)-2-Methylpropane-2-sulfinamide; (R)-(+)-2-Methyl-2-propanesulfinamide; (S)-(-)-2-Methyl-2-propanesulfinamide solution; (R)-(+)-2-Methyl-2-propanesulfinamide; (S)-(-)-2-Methyl-2-propanesulfinamide; (S)-(-)-tert-Butyl sulfinamide; (R)-(+)-tert-Butyl sulfinamide; (S)-(-)-2-甲基-2-丙烷亚磺酰胺 溶液; (R)-(+)-2-甲基-2-丙烷亚磺酰胺; (S)-(-)-2-甲基-2-丙烷亚磺酰胺; (S)-(-)-2-甲基-2-丙烷亚磺酰氨; (R)-(+)-2-甲基-2-丙烷磺酰亚氨

Database IDs

• CAS Number: 196929-78-9; 343338-28-3
• MDL Number: MFCD05861479; MFCD05861480
• PubChem SID: 24873117; 24873681; 162033131
• PubChem CID: 11355477

CALCULATED PROPERTIES

• Acid pKa: 16.748573
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 0.3126
• LogD (pH = 7.4): 0.3126
• Log P: 0.3126
• Molar Refractivity: 30.801 cm^3
• Polarizability: 12.858688 Å^3
• Polar Surface Area: 43.09 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 103-107 °C(lit.); 97-101 °C(lit.); 97-101°C; ca 100-105°C
• Flash Point: <-18.4 °F; <-28 °C
• Density: 0.895 g/mL at 25 °C
• Refractive Index: n20/D 1.418
• Optical Rotation: [α]20/D +4°, c = 1.0242 in chloroform stab. with amylenes; [α]20/D -4.5°, c = 1 in chloroform; [α]22/D -1.0°, c = 0.5 in chloroform

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Flammable (F); Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 11-19-36/37
• Safety Statements: 16-26
• TSCA Listed: false; 否
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H319-H335
• GHS Precautionary statements: P210-P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Supplemental Hazard Statements: May form explosive peroxides.
• Storage Temperature: 2-8°C

Product Information

• Purity: 95+%; 97%; 98%
• Concentration: 1 M in THF
• Contains: BHT as inhibitor
• Linear Formula: (CH3)3CS(O)NH2
• Empirical Formula (Hill Notation): C4H11NOS

DETAILS

Sigma Aldrich - 497401

Application
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.1
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
Packaging
1, 5 g in glass bottle
25 g in poly bottle

Sigma Aldrich - 513210

Application
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.1
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.
Ellman′s Sulfinamides
Packaging
1, 5, 25 g in glass bottle

Sigma Aldrich - 737127

Packaging
10 mL in glass bottle
50 mL in poly bottle