World Library  
Flag as Inappropriate
Email this Article

Methyl carbamate

Article Id: WHEBN0004429975
Reproduction Date:

Title: Methyl carbamate  
Author: World Heritage Encyclopedia
Language: English
Subject: Carbamate, Carbamic acid, Carbamates, List of IARC Group 3 carcinogens, Miřetice
Publisher: World Heritage Encyclopedia

Methyl carbamate

Methyl carbamate
Structural formula
Ball-and-stick model
CAS number  N
ChemSpider  YesY
Jmol-3D images Image 1
Molecular formula C2H5NO2
Molar mass 75 g/mol
Appearance white solid
Density 1.136 (56 °C)
Melting point 52 °C (126 °F; 325 K)
Boiling point 177 °C (351 °F; 450 K)
Solubility in water good
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N   YesY/N?)

Methyl carbamate (also called methylurethane, or urethylane) is an carbamic acid (H2NCO2H). It is a colourless solid.[1]

Methyl carbamate is prepared by the reaction of methanol and urea:

CO(NH2)2 + CH3OH → CH3OC(O)NH2 + NH3

It also forms in the reaction of ammonia with methyl chloroformate or dimethyl carbonate.


  • Safety and occurrence 1
  • Production, Use, and Exposure 2
  • See also 3
  • References 4
  • External links 5

Safety and occurrence

Unlike its close relative ethyl carbamate it is not mutagenic in salmonella (it tested negative in the Ames test), but it is mutagenic in Drosophila.[2] Experimental evidence does show that it is a carcinogen in rat, and not carcinogenic in mice. The compound is "known to the state of California to cause cancer" per Proposition 65.[3]

Production, Use, and Exposure

The compound was detected in wines preserved with dimethyl dicarbonate.[4]

Methyl carbamate is used primarily in the textile and polymer industries as a reactive intermediate. In the textile industry, it is used in the manufacture of dimethylol methyl carbamate-based resins that are applied on polyester cotton blend fabrics as durable-press finishes. The treated fabrics have good crease-angle retention, resist acid souring in commercial laundries, do not retain chlorine, and have flame-retardant properties. Methyl carbamate also is used in the manufacture of pharmaceuticals, insecticides, and urethane.[5]

N-Methyl carbamates are widely used as insecticides.[6] They have anticholinesterase activity without a cumulative effect.

See also


  1. ^ Peter Jäger, Costin N. Rentzea and Heinz Kieczka "Carbamates and Carbamoyl Chlorides" in Ullmann's Encyclopedia of Industrial Chemistry, 2012, Wiley-VCH, Weinheim. doi:10.1002/14356007.a05_051
  2. ^ P. Foureman, J.M. Mason, R. Valencia and S. Zimmering, Environ. Mol. Mutagen., 1994, 23 (1), 51 - 63.
  3. ^ OEHHA
  4. ^
  5. ^ National Toxocology Program
  6. ^ National Pesticide Information Center at Oregon State University

External links

  • MSDS
  • 1987 NIH study of methyl carbamate's carcinogenicity (PDF file)
This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.

Copyright © World Library Foundation. All rights reserved. eBooks from Hawaii eBook Library are sponsored by the World Library Foundation,
a 501c(4) Member's Support Non-Profit Organization, and is NOT affiliated with any governmental agency or department.