Methyl carbamate

Methyl carbamate
IUPAC name Methyl carbamate
Identifiers
CAS number	598-55-0 Y
PubChem	11722
ChemSpider	11229 Y
KEGG	C19445 N
ChEMBL	CHEMBL1085707 Y
Jmol-3D images	Image 1
SMILES O=C(OC)N
InChI InChI=1S/C2H5NO2/c1-5-2(3)4/h1H3,(H2,3,4) Y Key: GTCAXTIRRLKXRU-UHFFFAOYSA-N Y InChI=1/C2H5NO2/c1-5-2(3)4/h1H3,(H2,3,4) Key: GTCAXTIRRLKXRU-UHFFFAOYAJ
Properties
Molecular formula	C2H5NO2
Molar mass	75 g/mol
Melting point	52 °C, 325 K, 126 °F
Boiling point	177 °C, 450 K, 351 °F
N carbamate (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 US 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.^[1] 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.^[2]

The compound was detected in wines preserved with dimethyl dicarbonate.^[3]

Methyl carbamate is used by the textile industry to manufacture resins to be applied on polyester/cotton blend fabrics as durable-press finishes.^[4]

N-Methyl carbamates are widely used as insecticides.^[5]

See also

• Carbamate
• Urethane

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

• MSDS
• 1987 NIH study of methyl carbamate's carcinogenicity (PDF file)