2-Methylpropane-2-sulfinamide

Base Information

• Chemical Name: 2-Methylpropane-2-sulfinamide
• CAS No.: 146374-27-8
• 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: 146374-27-8.mol

Synonyms:tert-butanesulfinamide

Chemical Property of 2-Methylpropane-2-sulfinamide

Chemical Property:

• Vapor Pressure: 0.116mmHg at 25°C
• Melting Point: 97-101 °C
• Refractive Index: 1.523
• Boiling Point: 220 °C at 760 mmHg
• PKA: 10.11±0.50(Predicted)
• Flash Point: 86.8 °C
• PSA: 62.30000
• Density: 1.124 g/cm³
• LogP: 1.97330
• Storage Temp.: 2-8°C
• Solubility.: Soluble in methanol.
• 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

tert-Butylsulfinamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)S(=O)N
• Description: (S)-tert-Butanesulfinamide (also known as 2-Methyl-2-propanesulfinamide) is used for the synthesis of 4-sulfonyliminopiperidine and its reaction with benzyl Grignard to form an important pharmaceutical building block, 4-benzyl-4-aminopiperidne.It can be also used to prepare spiro tosylaziridines via methylene insertion into the derived sulfonylimine1,2-(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. (S)-(-)-2-Methyl-2-propanesulfinamide may be used to develop benzofuran-based farnesyltransferase inhibitors as anti-cancer agents.
• Uses: (±)-2-Methyl-2-propanesulfinamide is used in the synthesis of 4-sulfonyliminopiperidine and its reaction with benzyl Grignard to form an important pharmaceutical building block, 4-benzyl-4-aminopiperidne. It is also used to prepare spiro tosylaziridines via methylene insertion into the derived sulfonylimine. Ellman′s Sulfinamides

Technology Process of 2-Methylpropane-2-sulfinamide

There total 14 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: 98.0%

tert-butylsulfinyl chloride (31562-43-3) → S-tert-butylsulfinimide (146374-27-8)

Guidance literature:

With ammonium hydroxide;

DOI:10.1021/jo990271w

Reference yield: 50.0%

(S,E)-2-methyl-N-(3-phenylpropylidene)propane-2-sulfinamide → 2-methyl-propane-2-sulfinic acid (2-benzyl-5-phenyl-pent-2-enylidene)-amide + S-tert-butylsulfinimide (146374-27-8)

Guidance literature:

With tetrabutyl ammonium fluoride; phosphorus pentoxide; In diethyl ether; at 25 ℃; for 0.5h;

DOI:10.1055/s-2006-956466

Reference yield: 50.0%

2-methylpropan-2-thiol (75-66-1) → S-tert-butylsulfinimide (146374-27-8)

Guidance literature:

With methanol; [2,2]bipyridinyl; O-pivaloylhydroxylamine trifluoromethanesulfonate salt; iron(II) chloride; In dichloromethane; at 25 ℃; for 16h; Sealed tube;

DOI:10.1002/anie.202011138

upstream raw materials:

tert-butylsulfinyl chloride

C₁₂H₁₇NOS

Isobutane

tert-butylsulfinyl bromide

Downstream raw materials:

t-butylsulfonamide

N-cyclohexylidene-2-methylpropane-2-sulfinamide

2-methyl-N-((1E)-phenylmethylidene)-2-propanesulfinamide

N-(4-methoxybenzylidene)-2-methylpropane-2-sulfinamide

Refernces

Enantioselective Aza-Henry reaction with an N-sulfinyl urea organocatalyst

10.1021/ja075653v

The research explores the development of a new class of urea-based organocatalysts with an N-sulfinyl substituent that serves both as an acidifying group and a chiral controlling element. The purpose of this study is to enhance the enantioselectivity in the aza-Henry reaction, which involves the addition of nitroalkanes to imines, by using these novel organocatalysts. The researchers synthesized various N-sulfinyl urea and thiourea catalysts and tested their performance in the aza-Henry reaction. Key chemicals used in the study include tert-butanesulfinamide, isocyanates, isothiocyanates, and nitroethane. The study concludes that N-sulfinyl ureas are effective organocatalysts, achieving high enantioselectivity and diastereoselectivity in the aza-Henry reaction with both aromatic and aliphatic N-Boc imines. Notably, this is the first report of enantioselective H-bonding-catalyzed additions to aliphatic N-Boc imines. The findings highlight the potential of N-sulfinyl ureas as versatile and efficient organocatalysts for asymmetric synthesis.

First sonochemical, simple and solvent-free synthesis of chiral tert-butanesulfinimines using silica supported p-toluenesulfonic acid

10.1080/00397911.2018.1540047

The research presents a solvent-free, sonochemical method for synthesizing chiral tert-butanesulfinimines using silica-supported p-toluenesulfonic acid (pTSA-SiO2) as a catalyst. This green chemistry approach leverages ultrasound technology to enhance reaction efficiency, yielding high-quality products with minimal waste and without the need for toxic solvents. The study explores the synthesis of various tert-butanesulfinimines from different aldehydes under optimized conditions, achieving excellent yields and demonstrating the versatility and environmental benefits of the method. Key chemicals involved include chiral tert-butanesulfinamides, various aldehydes (aromatic, aliphatic, and heteroaromatic), and the pTSA-SiO2 catalyst, which facilitates the condensation reaction under solvent-free and aerobic conditions.

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