Methyl carbamate

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Methyl carbamate
Structural formula
Ball-and-stick model
Names
IUPAC name
Methyl carbamate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.009.037
KEGG
Properties
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)
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Methyl carbamate (also called methylurethane, or urethylane) is an organic compound and the simplest ester of 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[edit]

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 rats, 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[edit]

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[edit]

References[edit]

  1. ^ Jäger, Peter; Rentzea, Costin N.; Kieczka, Heinz (2005), "Carbamates and Carbamoyl Chlorides", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a05_051 
  2. ^ Foureman P, Mason JM, Valencia R, Zimmering S (1994). "Chemical mutagenesis testing in Drosophila. IX. Results of 50 coded compounds tested for the National Toxicology Program". Environ. Mol. Mutagen. 23 (1): 51–63. PMID 8125083. 
  3. ^ OEHHA
  4. ^ Inchem.org
  5. ^ National Toxocology Program
  6. ^ National Pesticide Information Center at Oregon State University

External links[edit]