1258328-05-0

Basic information

• Product Name: O-(4-phenylphenyl) N-methyl-N-phenyl thiocarbamate
• Synonyms: O-(4-phenylphenyl) N-methyl-N-phenyl thiocarbamate
• CAS NO: 1258328-05-0
• Molecular Weight: 319.427
• Mol File: 1258328-05-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: O-(4-phenylphenyl) N-methyl-N-phenyl thiocarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: O-(4-phenylphenyl) N-methyl-N-phenyl thiocarbamate(1258328-05-0)
• EPA Substance Registry System: O-(4-phenylphenyl) N-methyl-N-phenyl thiocarbamate(1258328-05-0)

Safety Data

• Hazardous Substances Data: 1258328-05-0(Hazardous Substances Data)

Upstream product

• 3185-68-0 O-biphenyl-4-yl chlorothioformate 
• 100-61-8 N-methylaniline 
• 463-71-8 thiophosgene 
• 92-69-3 4-Phenylphenol 

Downstream Products

• 349407-14-3 N-methyl-N-phenyl-[1,1'-biphenyl]-4-carboxamide 

Relevant articles and documents

Metal-free transformation of phenols into substituted benzamides: A highly selective radical 1,2-O→C transposition in O-aryl-N-phenylthiocarbamates

Radical merry-go-round: A highly efficient metal-free transformation of phenols into benzamides is designed through one-step conversion of phenols to aryl thiocarbamates and a subsequent radical addition/rearrangement/ fragmentation cascade. Computational analysis fully rationalizes the experimentally observed selectivity. Despite the possible competition from N-C fragmentation and N-neophyl rearrangement, the transformation exclusively follows the most kinetically and thermodynamically favored O-neophyl rearrangement path.

Radical OfC transposition: A metal-free process for conversion of phenols into benzoates and benzamides

We report a metal-free procedure for transformation of phenols into esters and amides of benzoic acids via a new radical cascade. Diaryl thiocarbonates and thiocarbamates, available in a single high-yielding step from phenols, selectively add silyl radicals at the sulfur atom of the CdS moiety. This addition step, analogous to the first step of the Barton-McCombie reaction, produces a carbon radical which undergoes 1,2 OfC transposition through an O-neophyl rearrangement. The usually unfavorable equilibrium in the reversible rearrangement step is shifted forward via a highly exothermic C-S bond scission in the O-centered radical, which furnishes the final benzoic ester or benzamide product. The metal-free preparation of benzoic acid derivatives from phenols provides a potentially useful alternative to metal-catalyzed carbonylation of aryl triflates.