50686-12-9

Basic information

• Product Name: (4-nitro-phenyl)-carbamic acid p-tolyl ester
• CAS NO: 50686-12-9
• Molecular Weight: 272.26
• Mol File: 50686-12-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (4-nitro-phenyl)-carbamic acid p-tolyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (4-nitro-phenyl)-carbamic acid p-tolyl ester(50686-12-9)
• EPA Substance Registry System: (4-nitro-phenyl)-carbamic acid p-tolyl ester(50686-12-9)

Safety Data

• Hazardous Substances Data: 50686-12-9(Hazardous Substances Data)

Upstream product

• 636-97-5 N-amino-(4-nitrophenyl)carboxamide 
• 100-01-6 4-nitro-aniline 
• 937-62-2 p-tolyl chloroformate 
• 106-44-5 p-cresol 
• 2733-41-7 4-nitrobenzoyl azide 

Relevant articles and documents

Nucleophilic substitution reactions of phenyl chloroformates

Methanolysis and aminolysis of phenyl chloroformates in acetonitrile have been investigated.The rates are slow due to initial-state stabilization by strong resonance electron donation from the phenoxy group.In both reactions the large positive values of ρY = 0.8-1.6 and low ΔH(excit.) and ΔS(excit.) values show that the transition state is strongly associative with little bond breaking.This mechanism is supported by the relatively large solvent isotope effect, kMeOH/kMeOD = ca. 2.3-2.5, and by the relatively strong inverse secondary kinetic isotope effect, kH/kD =/ca. 0.74-0.94, involving deuteriated aniline nuclephiles, in addition to a negative value of ρXY.The dependence on aniline basicity, βx(βnuc) =/ca. 0.8, and the ρX values of -2.3 are similar to those corresponding values for the reactions of benzoyl chlorides which have been predicted to react by an associative SN2 mechanism.These observations are consistent with a concerted displacement mechanism for the methanolysis and aminolysis of phenyl chloroformates.