51422-77-6

Basic information

• Product Name: (3-Methoxyphenyl)carbamic acid methyl ester
• Synonyms: (3-Methoxyphenyl)carbamic acid methyl ester;3-Methoxyphenylcarbamic acid methyl ester;N-(3-Methoxyphenyl)carbamic acid methyl ester;METHYL N-(3-METHOXYPHENYL)CARBAMATE
• CAS NO: 51422-77-6
• Molecular Formula: C₉H₁₁NO₃
• Molecular Weight: 181.19
• Mol File: 51422-77-6.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3-Methoxyphenyl)carbamic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3-Methoxyphenyl)carbamic acid methyl ester(51422-77-6)
• EPA Substance Registry System: (3-Methoxyphenyl)carbamic acid methyl ester(51422-77-6)

Safety Data

• Hazardous Substances Data: 51422-77-6(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 2597-44-6 formyl radical 
• 555-03-3 3-nitroanisole 
• 5813-86-5 m-methoxybenzamide 
• 195133-73-4 1,1-diisopropyl-3-(3-methoxyphenyl)urea 
• 201230-82-2 carbon monoxide 
• 6294-89-9 hydrazinecarboxylic acid methyl ester 
• 536-90-3 m-Anisidine 
• 124-38-9 carbon dioxide 
• 681-84-5 tetramethylorthosilicate 
• 18908-07-1 3-methoxyphenyl isocyanate 
• 138835-54-8 2,4,6-trinitrophenyl methyl carbonate 
• 139-77-5 1-(3-methoxyphenyl)urea 
• 79-22-1 methyl chloroformate 

Downstream Products

• 519157-20-1 N-(2-butynyl)-N-(methoxycarbonyl)-3-amino-1-methoxybenzene 

Relevant articles and documents

Reductive Carbonylation of Nitroarenes Using a Heterogenized Phen-Pd Catalyst

The reductive carbonylation of nitroarenes in the presence of MeOH and CO(g) is one of the interesting alternative routes without utilizing toxic phosgene and corrosive HCl generation for the synthesis of industrially useful carbamate compounds that serve as important intermediates for polyurethane production. Since homogeneous palladium catalysts supported by phen (phen = 1,10-phenanthroline) are known to be effective for this catalysis, the heterogenized Pd catalyst was developed using the phen-containing solid support. In this study, we report the synthesis of a phen-based heterogeneous Pd catalyst, Pd@phen-POP, which involves the solvent knitting of a phen scaffold via the Lewis-acid-catalyzed Friedel-Crafts reaction using dichloromethane as a source for linker in the presence of AlCl3 as a catalyst. The resulting solid material has been thoroughly characterized by various physical methods revealing high porosity and surface area. Similar to the homogeneous pallidum catalyst, this heterogeneous catalyst shows efficient reductive carbonylation of various nitroarenes. The catalytic reaction using nitrobenzene as a model compound presents a high turnover number (TON = 530) and a reasonable turnover frequency (TOF = 45 h-1), with a high selectivity (92%) for the carbamate formation. According to the recycling study, the heterogeneous catalyst is recyclable and retains ～90% of the original reactivity in each cycle.

Copper-Catalyzed Coupling of Amines with Carbazates: An Approach to Carbamates

A new approach for the preparation of carbamatesviathe copper-catalyzed cross-coupling reaction of amines with alkoxycarbonyl radicals generated from carbazates is described. This environmentally friendly protocol takes place under mild conditions and is compatible with a wide range of amines, including aromatic/aliphatic and primary/secondary substrates.

Phosgene-free synthesis of carbamates using co2 and titanium alkoxides

A facile one-pot, phosgene-free method for the synthesis of N-phenylcarbamates is developed. Using this method, various aromatic carbamates could be prepared from aromatic amines, CO2 and metal alkoxides. Aniline reacted with titanium methoxide (Ti(OMe)4)) in the presence of CO2 (5 MPa) to give methyl N-phenylcarbamate in 85% yield, in 20min. Titanium residue could be regenerated by reaction with dimethyl carbonate at 220 °C for 16 h.