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Methyl carbamate

Methyl carbamate

IUPAC name	Methyl carbamate
Identifiers
CAS number	598-55-0
PubChem	11722
SMILES	COC(=O)N
Properties
Molecular formula	C₂H₅NO₂
Molar mass	89.09 g/mol
Melting point	52 °C, 325 K, 126 °F
Boiling point	177 °C, 450 K, 351 °F
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and 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.

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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]