Methyl carbamate

Names
Preferred IUPAC name

Methyl carbamate

Identifiers

CAS Number

* 598-55-0 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:76606 N

ChEMBL |

* ChEMBL1085707 Y

ChemSpider |

* 11229 Y

KEGG |

* C19445 N

PubChem CID

* 11722

UNII |

* 9WFX634X2T Y

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

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

| 20 g/L[1]

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

Methyl carbamate (also called methylurethane, or urethylane) is an organic compound and the simplest ester of carbamic acid (H2NCO2H). It is a colourless solid.[2]

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.

## Contents

* 1 Safety and occurrence
* 2 Production, use, and exposure
* 3 See also
* 4 References
* 5 External links

## 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.[3] 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.[4]

## Production, use, and exposure

The compound was detected in wines preserved with dimethyl dicarbonate.[5]

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.[6]

N-Methyl carbamates are widely used as insecticides.[7] They have anticholinesterase activity without a cumulative effect.

## See also

* Carbamate
* Ethyl carbamate (urethane)

## References

1. ↑ "Alfa Aesar Methyl carbamate". Alfa Aesar. https://www.fishersci.com/shop/products/methyl-carbamate-99-4/AAA1652318.
2. ↑ Jäger, Peter; Rentzea, Costin N.; Kieczka, Heinz. "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_051.
3. ↑ "Chemical mutagenesis testing in Drosophila. IX. Results of 50 coded compounds tested for the National Toxicology Program". Environ. Mol. Mutagen. 23 (1): 51–63. 1994. PMID 8125083.
4. ↑ OEHHA
5. ↑ Inchem.org
6. ↑ National Toxocology Program
7. ↑ National Pesticide Information Center at Oregon State University

## External links

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

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*[CID]: Compound ID