51956-88-8

Basic information

• Product Name: O-(4-methoxybenzyl) N,N-dimethylthiocarbamate
• Synonyms: O-(4-methoxybenzyl) N,N-dimethylthiocarbamate
• CAS NO: 51956-88-8
• Molecular Weight: 225.312
• Mol File: 51956-88-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: O-(4-methoxybenzyl) N,N-dimethylthiocarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: O-(4-methoxybenzyl) N,N-dimethylthiocarbamate(51956-88-8)
• EPA Substance Registry System: O-(4-methoxybenzyl) N,N-dimethylthiocarbamate(51956-88-8)

Safety Data

• Hazardous Substances Data: 51956-88-8(Hazardous Substances Data)

Upstream product

• 16420-13-6 N,N-Dimethylthiocarbamoyl chloride 
• 105-13-5 4-Methoxybenzyl alcohol 

Downstream Products

• 6258-60-2 p-methoxybenzylmercaptan 

Relevant articles and documents

Benzylic Thio and Seleno Newman-Kwart Rearrangements

The thermally induced OBn → SBn and OBn → SeBn migration reactions facilitate the rearrangement of O-benzyl thio- and selenocarbamates [BnOC(=X)NMe2] (X = S or Se) into their corresponding S-benzyl thio- and Se-benzyl selenocarbamates [BnXC(=O)NMe2] (X = S or Se). A series of substituted O-benzyl thio- and selenocarbamates were synthesized and rearranged in good yields of 33-88%. The reaction rates are higher for substrates with electron-donating groups in the 2 or 4 position of the aromatic ring, but the rearrangement also proceeds with electron-withdrawing substituents. The rearrangement follows first-order reaction kinetics and proceeds via a tight ion pair intermediate consisting of the benzylic carbocation and the thio- or selenocarbamate moiety. Computational studies support these findings.