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{{chembox
{{Chembox new
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 486593232
| ImageFile = Methyl carbamate.png | ImageFile = Methyl carbamate.png
| ImageSize = 150px | ImageSize = 150px
| ImageName = Structural formula
⚫ | IUPACName = Methyl carbamate
| ImageFile1 = Methyl-carbamate-3D-balls.png
| ImageSize1 = 180px
| ImageName1 = Ball-and-stick model
⚫ | PIN = Methyl carbamate
| OtherNames = | OtherNames =
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | CASNo = 598-55-0
| PubChem = 11722 | ChemSpiderID = 11229
| InChI = 1/C2H5NO2/c1-5-2(3)4/h1H3,(H2,3,4)
⚫ | SMILES = COC(=O)N
| InChIKey = GTCAXTIRRLKXRU-UHFFFAOYAJ
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 76606
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1085707
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C2H5NO2/c1-5-2(3)4/h1H3,(H2,3,4)
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| StdInChIKey = GTCAXTIRRLKXRU-UHFFFAOYSA-N
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⚫ | CASNo = 598-55-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9WFX634X2T
| PubChem = 11722
⚫ | SMILES = O=C(OC)N
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C19445
⚫ }}
|Section2={{Chembox Properties
⚫ | Formula = C<sub>2</sub>H<sub>5</sub>NO<sub>2</sub>
| MolarMass =75 g/mol
| Appearance = white solid
| Density = 1.136 (56 °C)
⚫ | MeltingPtC = 52
⚫ | BoilingPtC = 177
| Solubility = 20 g/L<ref>{{cite web |title=Alfa Aesar Methyl carbamate |url=https://www.fishersci.com/shop/products/methyl-carbamate-99-4/AAA1652318 |website=Alfa Aesar |publisher=Alfa Aesar |access-date=4 October 2021}}</ref>
}} }}
| Section2 = {{Chembox Properties |Section3={{Chembox Hazards
⚫ | MainHazards =
⚫ | Formula = C<sub>2</sub>H<sub>5</sub>N<sub></sub>O<sub>2</sub>
| MolarMass =75 g/mol | FlashPt =
| Appearance = | AutoignitionPt =
| Density =
⚫ | MeltingPtC = 52
⚫ | BoilingPtC = 177
| Solubility =
⚫ }}
| Section3 = {{Chembox Hazards
⚫ | MainHazards =
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'''Methyl carbamate''' (also called '''methylurethane''', or '''urethylane''') is an ] and the simplest ester of the hypothetical ] (NH<sub>2</sub>COOH). Its sum formula is C<sub>2</sub>H<sub>5</sub>NO<sub>2</sub>. '''Methyl carbamate''' (also called '''methylurethane''', or '''urethylane''') is an ] and the simplest ester of ] (H<sub>2</sub>NCO<sub>2</sub>H). It is a colourless solid.<ref>{{Ullmann|date=2012|first1=Peter|last1=Jäger|first2=Costin N.|last2=Rentzea|first3=Heinz|last3=Kieczka|title=Carbamates and Carbamoyl Chlorides|doi=10.1002/14356007.a05_051}}</ref>

Methyl carbamate is prepared by the reaction of ] and ]:
:CO(NH<sub>2</sub>)<sub>2</sub> + CH<sub>3</sub>OH → CH<sub>3</sub>OC(O)NH<sub>2</sub> + NH<sub>3</sub>
It also forms in the reaction of ] with ] or ].


==Safety and occurrence==
Methyl carbamate is formed by the reaction of ] with ] or ]. According to ] ] number 2834799 ] can be reacted with ] to form it using ] as a reagent. Unlike its close relative ] it is not mutagenic in ] (it tested negative in the ]), but it is mutagenic in ].<ref>P. Foureman, J.M. Mason, R. Valencia and S. Zimmering, ''Environ. Mol. Mutagen.'', 1994, '''23''' (1), 51 - 63.</ref> Experimental evidence does show that it is a carcinogen in ], and not carcinogenic in mice. The compound is "known to the state of California to cause cancer" per ].<ref></ref> Unlike its close relative ] it is not mutagenic in '']'' (it tested negative in the ]), but it is mutagenic in '']''.<ref name="pmid8125083">{{cite journal |vauthors = Foureman P, Mason JM, Valencia R, Zimmering S |title=Chemical mutagenesis testing in Drosophila. IX. Results of 50 coded compounds tested for the National Toxicology Program |journal=Environ. Mol. Mutagen. |volume=23 |issue=1 |pages=51–63 |year=1994 |pmid=8125083 }}</ref> Experimental evidence does show that it is a carcinogen in ]s, and not carcinogenic in mice. The compound is "known to the state of California to cause cancer" per ].<ref> {{webarchive|url=https://web.archive.org/web/20060512183340/http://www.oehha.ca.gov/prop65/prop65_list/files/P65single20306.pdf |date=2006-05-12 }}</ref>


==Production, use, and exposure==
The compound was detected in ]s preserved with ].<ref></ref> The compound was detected in ]s preserved with ].<ref></ref>


Methyl carbamate is used by the textile industry to manufacture resins to be applied on polyester/cotton blend fabrics as durable-press finishes.<ref></ref> 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.<ref></ref>


] are widely used as insecticides.<ref></ref> ] are widely used as insecticides.<ref></ref> They have ] activity without a cumulative effect.


==See also== ==See also==
*] *]
*] (urethane)
*]


==References== ==References==
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] ]
] ]

Latest revision as of 15:31, 7 August 2022

Methyl carbamate
Structural formula
Ball-and-stick model
Names
Preferred IUPAC name Methyl carbamate
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.037 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H5NO2/c1-5-2(3)4/h1H3,(H2,3,4)Key: GTCAXTIRRLKXRU-UHFFFAOYSA-N
  • 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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

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

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 rats, and not carcinogenic in mice. The compound is "known to the state of California to cause cancer" per Proposition 65.

Production, use, and exposure

The compound was detected in wines preserved with dimethyl dicarbonate.

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.

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

See also

References

  1. "Alfa Aesar Methyl carbamate". Alfa Aesar. Alfa Aesar. Retrieved 4 October 2021.
  2. Jäger, Peter; Rentzea, Costin N.; Kieczka, Heinz (2012). "Carbamates and Carbamoyl Chlorides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_051. ISBN 978-3527306732.
  3. 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.
  4. OEHHA Archived 2006-05-12 at the Wayback Machine
  5. Inchem.org
  6. National Toxocology Program
  7. National Pesticide Information Center at Oregon State University

External links

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