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
• Uses: suzuki reaction, useful reagent for synthesizing chiral amines. (R)-(+)-2-Methyl-2-propanesulfinamide is a chiral ligand, which is used in pharmaceutical compositions. Further, it is used in the preparation of beta-chloro sulfinamides in the synthesis of chiral azridines. It is involved in the preparation of organocatalyst for enantioselective reduction of imines. It serves as a reagent for synthesizing chiral amines. In addition to this, it is converted into P,N-sulfinyl imine ligands through condensation with aldehydes and ketones which undergoes iridium-catalyzed asymmetric hydrogenation of olefins. Chiral ligand used in pharmaceutical compositions

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:

(R,E)-2-methyl-N-(phenylmethylene)-2-propanesulfinamide

(R_S)-2-methyl-N-(1-phenylpentylidene)propane-2-sulfinamide

(N(E),R)-2-methyl-N-(2-phenylethylidene)-2-propanesulfinamide

(R,E)-N-(4-methoxybenzylidene)-2-methylpropane-2-sulfinamide