500372-18-9

Basic information

• Product Name: O-(2-bromobenzyl) 2-methyl carbonothioate
• Synonyms: O-(2-bromobenzyl) 2-methyl carbonothioate
• CAS NO: 500372-18-9
• Molecular Weight: 261.139
• Mol File: 500372-18-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: O-(2-bromobenzyl) 2-methyl carbonothioate(CAS DataBase Reference)
• NIST Chemistry Reference: O-(2-bromobenzyl) 2-methyl carbonothioate(500372-18-9)
• EPA Substance Registry System: O-(2-bromobenzyl) 2-methyl carbonothioate(500372-18-9)

Safety Data

• Hazardous Substances Data: 500372-18-9(Hazardous Substances Data)

Upstream product

• 74-88-4 methyl iodide 
• 18982-54-2 o-bromobenzyl alcohol 
• 201230-82-2 carbon monoxide 
• 463-58-1 carbon oxide sulfide 

Downstream Products

• 80070-89-9 o-bromobenzyl chloroformate 

Relevant articles and documents

Solvent-assisted thiocarboxylation of amines and alcohols with carbon monoxide and sulfur under mild conditions

DMSO or DMF as a solvent strongly accelerated the thiocarboxylation of amines and alcohols with carbon monoxide and sulfur. Under mild conditions (1 atm, 20°C), this thiocarboxylation of amines assisted by DMSO with carbon monoxide and sulfur has been developed into a practical and convenient synthetic method for S-alkyl thiocarbamates in good to excellent yields, including EPTC, thiobencarb, orbencarb, and molinate (herbicides). DMF also showed the similar solvent effect. NMP slightly decreased the effect for the thiocarboxylation of amines, and the yield of S-alkyl thiocarbamate was lowered in DMAc. Surprisingly, no formation of S-alkyl thiocarbamate was observed at the use of the other solvents, such as THF, hexane, toluene, AcOEt, MeCN, MeOH, and H 2O. The present solvent-assisted thiocarboxylation with carbon monoxide and sulfur could be also applied to a new synthesis of S-alkyl O-alkyl carbonothioates from alcohols under mild conditions (1 atm, 20°C) in DMF using DBU (1,8-diazabicyclo[5.4.0]undec-7-ene).

Benzyl chloroformate (CbzCl) synthesis using carbon monoxide as a carbonyl source

A novel non-phosgene synthetic method for benzyl chloroformate (CbzCl) was established. S-Methyl O-benzyl carbonothioates were prepared by the carbonylation of benzyl alcohols with carbon monoxide and sulfur (or carbonyl sulfide) in the presence of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) followed by esterification using methyl iodide in good yields. Then, CbzCl derivatives were successfully synthesized by the chlorination of S-methyl O-benzyl carbonothioates using sulfuryl chloride in excellent yields.