|Jmol-3D images||Image 1|
|Molar mass||75 g/mol|
|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 noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
Methyl carbamate is prepared by the reaction of methanol and urea:
- CO(NH2)2 + CH3OH → CH3OC(O)NH2 + NH3
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 rat, and not carcinogenic in mice. The compound is "known to the state of California to cause cancer" per Proposition 65.
Production, Use, and Exposure
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.
- 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
- P. Foureman, J.M. Mason, R. Valencia and S. Zimmering, Environ. Mol. Mutagen., 1994, 23 (1), 51 - 63.
- National Toxocology Program
- National Pesticide Information Center at Oregon State University