Methylsulfenyl bromide

Base Information

• Chemical Name: Methylsulfenyl bromide
• CAS No.: 18681-52-2
• Molecular Formula: CH3 Br S
• Molecular Weight: 127.005
• Hs Code.: 2930909090
• DSSTox Substance ID: DTXSID20171943
• Nikkaji Number: J1.090.028J
• Wikidata: Q83042083
• Mol file: 18681-52-2.mol

Synonyms:methylsulfenyl bromide

Chemical Property of Methylsulfenyl bromide

Chemical Property:

• Vapor Pressure: 67.3mmHg at 25°C
• Boiling Point: 89°Cat760mmHg
• Flash Point: 7.6°C
• PSA: 25.30000
• Density: 1.759g/cm³
• LogP: 1.65930
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 125.91388
• Heavy Atom Count: 3
• Complexity: 4.8

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSBr

Technology Process of Methylsulfenyl bromide

There total 5 articles about Methylsulfenyl bromide 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:

dimethylsulfide (75-18-3) → methylsulfenyl bromide (18681-52-2) + dimethyl sulfoxide (67-68-5,8070-53-9)

Guidance literature:

With bromine; oxygen; at 25 ℃; under 750.06 Torr; Kinetics; Photolysis;

DOI:10.1002/(SICI)1097-4601(1999)31:12<883::AID-KIN7>3.0.CO;2-V

Reference yield:

Dimethyldisulphide (624-92-0) → methylsulfenyl bromide (18681-52-2)

Guidance literature:

With bromine; In dichloromethane; at 0 ℃;

DOI:10.1021/jo00189a040

Reference yield:

dimethylsulfide (75-18-3) → methylsulfenyl bromide (18681-52-2)

Guidance literature:

With bromine; In 1,2-dichloro-ethane; at 20 ℃; for 13h; Darkness;

DOI:10.1002/chem.200903294

upstream raw materials:

Dimethyldisulphide

methylthio radical

dimethylsulfide

Downstream raw materials:

3-Bromo-3-methyl-2-methylsulfanyl-N-phenyl-butyramide

2-(methylsulfenyl)phenol

methyl sulfenyl triflate

C₁₃H₁₉BrN₂OS₂

Refernces

Opening of thiiranes: Preparation of orthogonal protected 2-thioglyceraldehyde

10.1021/jo001392v

Michael G. Silvestri and Chi-Huey Wong detail an efficient procedure for the synthesis of an orthogonal-protected 2-thioglyceraldehyde derivative. The authors initially attempted various methods to introduce a sulfur atom next to the aldehyde functional group but encountered challenges. They discovered that treating acrolein diethyl acetal sulfide with methanesulfenyl bromide at low temperatures efficiently opened the thiirane ring to form a halo disulfide. This compound could then be easily transformed into a fully protected version of 2-thioglyceraldehyde through substitution reactions with silver acetate, sodium azide, sodium iodide, and silver nitrate. The study also explored the conversion of this protected aldehyde to its usable form and reported the preparation of additional analogues. The findings suggest that the methanesulfenyl bromide method could be generally applicable for thiirane ring opening and has potential for future synthetic applications, including enzymatic reactions.