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Methyl carbamate

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Methyl carbamate
Structural formula
Ball-and-stick model
Names
IUPAC name Methyl carbamate
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.037 Edit this at Wikidata
KEGG
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H5NO2/c1-5-2(3)4/h1H3,(H2,3,4)Key: GTCAXTIRRLKXRU-UHFFFAOYSA-N
  • InChI=1/C2H5NO2/c1-5-2(3)4/h1H3,(H2,3,4)Key: GTCAXTIRRLKXRU-UHFFFAOYAJ
SMILES
  • O=C(OC)N
Properties
Chemical formula C2H5NO2
Molar mass 75 g/mol
Melting point 52 °C (126 °F; 325 K)
Boiling point 177 °C (351 °F; 450 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Methyl carbamate (also called methylurethane, or urethylane) is an organic compound and the simplest ester of the hypothetical carbamic acid (NH2COOH). Its sum formula is C2H5NO2.

Methyl carbamate is formed by the reaction of ammonia with methyl chloroformate or methyl carbonate. According to United States patent number 2834799 urea can be reacted with methanol to form it using boron trifluoride as a reagent. 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. 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.

The compound was detected in wines preserved with dimethyl dicarbonate.

Methyl carbamate is used by the textile industry to manufacture resins to be applied on polyester/cotton blend fabrics as durable-press finishes.

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

See also

References

  1. P. Foureman, J.M. Mason, R. Valencia and S. Zimmering, Environ. Mol. Mutagen., 1994, 23 (1), 51 - 63.
  2. OEHHA
  3. Inchem.org
  4. National Toxocology Program
  5. National Pesticide Information Center at Oregon State University

External links

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