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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
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 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 carbamic acid (H2NCO2H). It is a colourless solid.

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

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 rats, and not carcinogenic in mice. The compound is "known to the state of California to cause cancer" per Proposition 65.

Production, use, and exposure

The compound was detected in wines preserved with dimethyl dicarbonate.

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.

N-Methyl carbamates are widely used as insecticides. 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. Foureman, P.; Mason, J. M.; Valencia, R.; Zimmering, S. (1994). Environ. Mol. Mutagen. 23 (1): 51–63. {{cite journal}}: Missing or empty |title= (help)
  3. OEHHA
  4. Inchem.org
  5. National Toxocology Program
  6. National Pesticide Information Center at Oregon State University

External links

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