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246352

Sigma-Aldrich

Methyl carbamate

98%

Synonym(s):

Urethylane

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About This Item

Linear Formula:
NH2COOCH3
CAS Number:
Molecular Weight:
75.07
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

form

crystals

bp

176-177 °C (lit.)

mp

56-58 °C (lit.)

solubility

alcohol: freely soluble(lit.)
water: freely soluble(lit.)

SMILES string

COC(N)=O

InChI

1S/C2H5NO2/c1-5-2(3)4/h1H3,(H2,3,4)

InChI key

GTCAXTIRRLKXRU-UHFFFAOYSA-N

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Application

Methyl carbamate was used in the synthesis of protected aminocyclopropanes.

Pictograms

Health hazardExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Carc. 2 - Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Methyl carbamate: negative results in mouse bone-marrow micronucleus test.
M D Shelby et al.
Mutation research, 260(4), 311-311 (1991-08-01)
Shingo Ishikawa et al.
Angewandte Chemie (International ed. in English), 52(38), 10060-10063 (2013-08-06)
Easy as 1,2,3: Reaction of methyl carbamate, triethyl orthoformate, and readily available alkenes provides a highly practical preparation of protected aminocyclopropanes. The reaction proceeds with preferential cis addition to alkenes, and cleavage of the methyl carbamate gives the free aminocyclopropanes
Genotoxicity data supporting the proposed metabolic activation of ethyl carbamate (urethane) to a carcinogen: the problem now posed by methyl carbamate.
J Ashby
Mutation research, 260(4), 307-308 (1991-08-01)
N P Sen et al.
Food additives and contaminants, 9(2), 149-160 (1992-03-01)
A method is described for the simultaneous determination of methyl carbamate (MC) and ethyl carbamate (EC) in wines that is based on: (a) extraction of the sample with dichloromethane using an extraction tube or an alumina-Celite column, (b) concentration of
P C Chan et al.
Japanese journal of cancer research : Gann, 83(3), 258-263 (1992-03-01)
Short-term and long-term carcinogenicity of methyl carbamate (MCB) was evaluated in F344 rats and B6C3F1 mice. In experiments lasting 6, 12, and 18 months, MCB was given in water by gavage to groups of 10 male and 10 female rats

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