63379-17-9

Basic information

• Product Name: Carbamic acid, (2-methyl-5-nitrophenyl)-, methyl ester
• CAS NO: 63379-17-9
• Molecular Formula: C9H10N2O4
• Molecular Weight: 210.189
• Mol File: 63379-17-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Carbamic acid, (2-methyl-5-nitrophenyl)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, (2-methyl-5-nitrophenyl)-, methyl ester(63379-17-9)
• EPA Substance Registry System: Carbamic acid, (2-methyl-5-nitrophenyl)-, methyl ester(63379-17-9)

Safety Data

• Hazardous Substances Data: 63379-17-9(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 121-14-2 2,4-dinitrotoluene 
• 14983-92-7 methyl N-(2-methylphenyl)carbamate 
• 79-22-1 methyl chloroformate 
• 99-55-8 2-methyl-5-nitroaniline 
• 924666-87-5 (2-methyl-5-nitroso-phenyl)-carbamic acid methyl ester 

Relevant articles and documents

Carbonylation of dinitrotoluene to dimethyl toluenedicarbamate; high efficiency of phosphorus acids as promoters for the palladium-phenanthroline catalytic system

Phosphorus acids are excellent promoters for the palladium-phenanthroline catalyzed carbonylation of 2,4-dinitrotoluene to 2,4-toluenedicarbamate. For the first time, all intermediate nitrocarbamates and aminocarbamates have been independently synthesized and their amount after every catalytic reaction precisely quantified. An extensive optimization of all experimental variables has been carried out. The best acids are phenylphosphonic and 4-tolylphosphonic acids. The addition of 2,2-dimethoxypropane as an internal drying agent is highly beneficial. The addition of an amine derived from the starting dinitroarene increases both rate and selectivity of the carbonylation reaction. The complexes [Pd(Phen)2] [SbF6] and [Pd(Phen) 2][BArF4] [ArF = 3,5-(CF 3)2C6H3] have been prepared for the first time. The latter displays a markedly higher solubility than all other [Pd(Phen)2]2+ complexes. The effect of several possible promoters has also been investigated. Under the optimized experimental conditions, a 77.6% selectivity in dicarbamate was obtained when working at a molar ratio dinitrotoluene/Pd = 2920. At the end of the reaction, the dicarbamate spontaneously precipitates out of the solution in high yields upon cooling, with no inclusion of the acid promoter or of phenanthroline. 2,6-Dinitrotoluene can also be efficiently carbonylated to the corresponding dicarbamate.

Synthesis of alkyl N-(C-nitrosoaryl)carbamates and some reactions thereof

Reactions of alkyl N-phenylcarbamates, m-di(methoxycarboxyamido)benzene, and methyl N-(o-tolyl)carbamate with nitrosylsulfuric acid in glacial acetic acid afford N-(C-nitrosoaryl)carbamates; under these conditions tert-bulyl N-phenylcarbamate suffers decarboxylation, methyl N-(p-tolyl)-, methyl N-(p-methoxyphenyl)carbamates, o-and p-di(methoxycarboxyamido)benzenes are nitrated, and isomeric methyl N-nitrophenylcarbamates and methyl N-(p-bromophenyl)carbamate do not react. The reduction of N-(C-nitrosoaryl)carbamates with dithionite afforded the corresponding aminocarbamates; the oxidation with nitric acid yielded carbamate nitro derivatives; the condensation with aniline and benzylpyridinium chloride resulted in carbamate derivatives of azobenzene and phenylnitron.