Methyl N-(3-nitrophenyl)carbamate

Base Information

• Chemical Name: Methyl N-(3-nitrophenyl)carbamate
• CAS No.: 2189-61-9
• Molecular Formula: C8H8N2O4
• Molecular Weight: 196.163
• DSSTox Substance ID: DTXSID90404134
• Nikkaji Number: J1.605.719C
• Wikidata: Q82208143
• Mol file: 2189-61-9.mol

Synonyms:Methyl N-(3-nitrophenyl)carbamate;2189-61-9;SCHEMBL5892586;DTXSID90404134;ZMHNYWIJOJZOJY-UHFFFAOYSA-N;3-(Methoxycarbonylamino)nitrobenzene;AKOS000371539

Chemical Property of Methyl N-(3-nitrophenyl)carbamate

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 196.04840674
• Heavy Atom Count: 14
• Complexity: 226

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)NC1=CC(=CC=C1)[N+](=O)[O-]

Technology Process of Methyl N-(3-nitrophenyl)carbamate

There total 13 articles about Methyl N-(3-nitrophenyl)carbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + 3-nitro-aniline (99-09-2) → (3-nitro-phenyl)-carbamic acid methyl ester (2189-61-9)

Guidance literature:

With copper diacetate; palladium diacetate; potassium iodide; In dimethyl sulfoxide; at 120 ℃; under 760.051 Torr;

DOI:10.1002/adsc.201100545

Reference yield:

methanol (67-56-1) + 1,1-diisopropyl-3-(3-nitrophenyl)urea (198763-88-1) → (3-nitro-phenyl)-carbamic acid methyl ester (2189-61-9) + diisopropylamine (108-18-9)

Guidance literature:

at 70 ℃; Kinetics;

DOI:10.1002/anie.200904435

Reference yield:

meta-dinitrobenzene (99-65-0) → dimethyl N,N'-(1,3-phenylene)dicarbamate (4930-04-5) + (3-nitro-phenyl)-carbamic acid methyl ester (2189-61-9) + 3-nitro-aniline (99-09-2)

Guidance literature:

With carbon monoxide; Pd(phen)2(OTf)2; In methanol; chlorobenzene; at 135 ℃; for 2h; under 45003.6 Torr; Yield given. Yields of byproduct given;

DOI:10.1039/cc9960000217

upstream raw materials:

methanol

isocyanic acid (3-nitro-phenyl) ester

3-nitrobenzoyl azide

3-nitro-benzoic acid bromoamide

Downstream raw materials:

methyl 3-(aminophenyl)carbamate

3-nitro-aniline

Refernces

• 1、 Usharani,Bhujanga Rao,Reddy,Dubey. "Synthesis of aryl urea derivatives from aryl amines and aryl isocyanates". scheme or table. p. 1802 - 1806. Retrieved 2011/12/22.
• 2、 Hutchby, Marc,Houlden, Chris E.,Gair Ford,Tyler, Simon N. G.,Gagne, Michel R.,Lloyd-Jones, Guy C.,Booker-Milburn, Kevin I.. "Hindered ureas as masked isocyanates: Facile carbamoylation of nucleophiles under neutral conditions". supporting information; experimental part. p. 8721 - 8724. Retrieved 2010/01/16.