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Methyl carbamate

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Methyl carbamate

Methyl carbamate
Structural formula
Ball-and-stick model
Identifiers
CAS number  N
PubChem
ChemSpider  YesY
KEGG  N
ChEBI  N
ChEMBL  YesY
Jmol-3D images Image 1
Properties
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.

Contents

  • 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

References

  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. ^ Inchem.org
  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)
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