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Revision as of 09:24, 25 February 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL.← Previous edit Latest revision as of 15:31, 7 August 2022 edit undoJWBE (talk | contribs)Extended confirmed users10,111 editsm (GR) File renamed: File:Methyl-carbmate-3D-balls.png → File:Methyl-carbamate-3D-balls.png Criterion 3 
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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 400307139
| Watchedfields = changed
⚫ | verifiedrevid = 486593232
| ImageFile = Methyl carbamate.png | ImageFile = Methyl carbamate.png
| ImageSize = 150px | ImageSize = 150px
| ImageName = Structural formula | ImageName = Structural formula
| ImageFile1 = Methyl-carbmate-3D-balls.png | ImageFile1 = Methyl-carbamate-3D-balls.png
| ImageSize1 = 180px | ImageSize1 = 180px
| ImageName1 = Ball-and-stick model | ImageName1 = Ball-and-stick model
| IUPACName = Methyl carbamate | PIN = Methyl carbamate
| OtherNames = | OtherNames =
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 11229 | ChemSpiderID = 11229
| InChI = 1/C2H5NO2/c1-5-2(3)4/h1H3,(H2,3,4) | InChI = 1/C2H5NO2/c1-5-2(3)4/h1H3,(H2,3,4)
| InChIKey = GTCAXTIRRLKXRU-UHFFFAOYAJ | InChIKey = GTCAXTIRRLKXRU-UHFFFAOYAJ
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 76606
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1085707 | ChEMBL = 1085707
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
Line 19: Line 24:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GTCAXTIRRLKXRU-UHFFFAOYSA-N | StdInChIKey = GTCAXTIRRLKXRU-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 598-55-0 | CASNo = 598-55-0
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem = 11722
| SMILES = O=C(OC)N | UNII = 9WFX634X2T
⚫ | PubChem = 11722
| SMILES = O=C(OC)N
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C19445
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>2</sub>H<sub>5</sub>N<sub></sub>O<sub>2</sub> | Formula = C<sub>2</sub>H<sub>5</sub>NO<sub>2</sub>
| MolarMass =75 g/mol | MolarMass =75 g/mol
| Appearance = | Appearance = white solid
| Density = | Density = 1.136 (56 °C)
| MeltingPtC = 52 | MeltingPtC = 52
| BoilingPtC = 177 | 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>
| Solubility =
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
}} }}
}} }}


'''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 ]:
⚫ 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>
: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==
⚫ 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 ].<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==