94563-12-9

Basic information

• Product Name: methyl 4-((methoxycarbonyl)amino)benzoate
• Synonyms: methyl 4-((methoxycarbonyl)amino)benzoate
• CAS NO: 94563-12-9
• Molecular Weight: 209.202
• Mol File: 94563-12-9.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: methyl 4-((methoxycarbonyl)amino)benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-((methoxycarbonyl)amino)benzoate(94563-12-9)
• EPA Substance Registry System: methyl 4-((methoxycarbonyl)amino)benzoate(94563-12-9)

Safety Data

• Hazardous Substances Data: 94563-12-9(Hazardous Substances Data)

Upstream product

• 616-38-6 carbonic acid dimethyl ester 
• 619-45-4 4-methoxycarbonyl aniline 
• 67-56-1 methanol 
• 6757-31-9 methyl-4-carbamoylbenzoate 
• 160852-85-7 2-[2-(2-methoxyethoxy)ethoxy]ethyl methyl carbonate 
• 79-22-1 methyl chloroformate 
• 20442-96-0 methyl 4-azidobenzoate 
• 103-71-9 phenyl isocyanate 
• 23138-53-6 methyl 4-isocyanatobenzoate 

Downstream Products

• 30063-17-3 4-[(methoxycarbonyl)amino]benzoic acid 

Relevant articles and documents

Zr-MOF-808@MCM-41 catalyzed phosgene-free synthesis of polyurethane precursors

In this work, a catalytic method is presented for the synthesis of aromatic carbamates from aromatic amines using dimethyl carbonate instead of phosgene as a green and safe reaction process. Microcrystalline Zr-MOF-808 is reported as an active and efficient heterogeneous catalyst for the selective carbamoylation of anilines and industrially relevant aromatic diamines, under mild reaction conditions with near quantitative yields. We have accomplished the selective growth of well-dispersed Zr-MOF-808 nanocrystals within the mesoporous material MCM-41. A superior catalytic performance of the Zr-MOF-808@MCM-41 is demonstrated that together with increased stability stands out as an advantageous heterogeneous catalyst for polyurethane production. In situ FTIR studies have allowed a better understanding of the reaction pathway at the molecular level when the active MOF catalyst is present.

Electrochemical Hofmann rearrangement mediated by NaBr: Practical access to bioactive carbamates

An electrochemical Hofmann rearrangement is reported. With the mediation of NaBr, highly corrosive and toxic halogens are avoided. Moreover, this efficient and green approach is well compatible with a broad range of amides, including several commercial medicine derivatives, and provides direct access to synthetically useful carbamates. The synthetic utility of this method is also demonstrated by the preparation of 15N labeling carbamate and gram-scale synthesis of Amantadine.

Selective N,N-dimethylation of primary aromatic amines with methyl alkyl carbonates in the presence of phosphonium salts

In the presence of onium salts, at 140-170 °C. methyl alkyl carbonates [1a-c, ROCO2Me, R = MeO(CH2)2[O(CH 2)2]n; n = 2-0, respectively] react with primary aromatic amines (XC6H4NH2, X = p-OMe, p-Me, H, p-Cl, p-CO2Me, o-Et, and 2,3-Me2C 6H3NH2) to yield the corresponding N,N-dimethyl derivatives (ArNMe2) with high selectivity (up to 96%) and good isolated yields (78-95%). Phosphonium salts (e.g., Ph3PEtI and n-Bu4PBr) are particularly efficient catalysts. Overall, a solvent-free reaction is coupled with safe methylating agents (1a-c) made from nontoxic dimethyl carbonate.