2-Methylpropane-2-sulfinamide

Base Information

• Chemical Name: 2-Methylpropane-2-sulfinamide
• CAS No.: 196929-78-9
• Molecular Formula: C4H11NOS
• Molecular Weight: 121.203
• Hs Code.: 29309090
• European Community (EC) Number: 926-811-8,619-964-4
• UNII: 42F4K704G0,I85YC2ZA8O,7FEC1T720F
• DSSTox Substance ID: DTXSID20391967,DTXSID90463241
• Nikkaji Number: J796.219C
• Wikipedia: Tert-Butanesulfinamide
• Wikidata: Q7705231
• Mol file: 196929-78-9.mol

Synonyms:tert-butanesulfinamide

Chemical Property of 2-Methylpropane-2-sulfinamide

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 103-107 °C(lit.)
• Refractive Index: 4 ° (C=1, CHCl3)
• Boiling Point: 219.957 °C at 760 mmHg
• PKA: 10.11±0.50(Predicted)
• Flash Point: 86.827 °C
• PSA: 62.30000
• Density: 1.124 g/cm³
• LogP: 1.97330
• Storage Temp.: Keep Cold
• Solubility.: Soluble in chloroform, methanol, tetrahydrofuran, dichloromethan
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 121.05613515
• Heavy Atom Count: 7
• Complexity: 84.2

Purity/Quality:

99% ^*data from raw suppliers

(R)-tert-Butylsulfinamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn,F
• Statements: 11-19-36/37-40-36/37/38
• Safety Statements: 22-24/25-36/37-26-16-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)S(=O)N
• General Description: (R)-(+)-2-Methyl-2-propanesulfinamide, also known as (R)-tert-butanesulfinamide, is a valuable chiral auxiliary widely used in asymmetric synthesis. It is efficiently synthesized via catalytic asymmetric oxidation of di-tert-butyl disulfide using a cost-effective chiral Schiff base ligand and H₂O₂ as the oxidant, yielding the intermediate tert-butyl tert-butanethiosulfinate with high enantioselectivity (91% ee). Subsequent nucleophilic displacement with LiNH₂ provides the sulfinamide in high yield (91%), which can be further purified to enantiomeric purity by recrystallization. This scalable method enables large-scale production, making (R)-(+)-2-Methyl-2-propanesulfinamide a practical reagent for stereoselective transformations, including the synthesis of sulfoxides, sulfinamides, and sulfinimines.

Technology Process of 2-Methylpropane-2-sulfinamide

There total 28 articles about 2-Methylpropane-2-sulfinamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(RS,S)-N-(3-hydroxy-1,3-diphenylpropylidene)-tert-butanesulfinamide (441788-45-0) → (S)-3-hydroxy-1,3-diphenyl-propan-1-one (42052-51-7,69897-46-7,72237-27-5,93059-59-7) + (R)-2-methylpropane-2-sulfinamide (196929-78-9)

Guidance literature:

With acetic acid; In methanol; at 40 ℃; for 20h;

DOI:10.1021/ja0363462

Reference yield: 98.0%

(RS,S)-N-(3-hydroxy-4-methyl-1-phenylpentylidene)-tert-butanesulfinamide (441788-43-8) → (S)-3-hydroxy-4-methyl-1-phenyl-1-pentanoate + (R)-2-methylpropane-2-sulfinamide (196929-78-9)

Guidance literature:

With acetic acid; In methanol; at 40 ℃; for 20h;

DOI:10.1021/ja0363462

Reference yield: 92.0%

(R)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl tert-butanesulfinate (159263-57-7) → (R)-2-methylpropane-2-sulfinamide (196929-78-9)

Guidance literature:

(R)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl tert-butanesulfinate; With lithium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 48h; Inert atmosphere;

With silica gel; In tetrahydrofuran; methanol; for 0.25h; Inert atmosphere;

DOI:10.1002/ejoc.201402673

upstream raw materials:

(R)-tert-butyl tert-butanethiosulfinate

(R_S)-N-benzyl-2-methylpropane-2-sulfinamide

(R)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl tert-butanesulfinate

2-Methyl-propane-2-sulfinic acid (1R,2S)-1-(2,4,6-trimethyl-benzenesulfonylamino)-indan-2-yl ester

Downstream raw materials:

Methyl 4-bromobutyrate

2-methyl-propane-2-sulfinic acid [4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-naphthalen-y-yl]-amide

2-methyl-propane-2-sulfinic acid [4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-naphthalen-yl]-amide

(R)-N-cyclopentylidene-2-methylpropane-2-sulfinamide