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Key Documents

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.)

functional group

amine

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

signalword

Warning

hcodes

Hazard Classifications

Carc. 2 - Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges


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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)
Methyl carbamate: negative results in mouse bone-marrow micronucleus test.
M D Shelby et al.
Mutation research, 260(4), 311-311 (1991-08-01)
R G Ames et al.
Archives of environmental health, 50(6), 440-444 (1995-11-01)
To test the hypothesis that chronic neurologic sequelae are associated with cholinesterase depression short of frank organophosphate poisoning, we compared 45 male subjects who had a history of moderate cholinesterase inhibition with 90 male subjects who had neither past cholinesterase
Geert Van Biesen et al.
Electrophoresis, 27(22), 4456-4468 (2006-10-24)
Ammonium perfluorooctanoate (APFOA) was investigated as an MS-friendly surfactant for the analysis of a mixture of ten N-methylcarbamates with MEKC-ESI-MS. Because of the relatively low boiling point of perfluorooctanoic acid ( approximately 190 degrees C), APFOA can be introduced into

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