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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:
598-55-0
Molecular Weight:
75.07
EC Number:
209-939-2
MDL number:
MFCD00007964
UNSPSC Code:
12352100
PubChem Substance ID:
24854803
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
GHS08,GHS07

signalword

Warning

hcodes

H319,H351

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
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
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
Xusheng Shao et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(43), 17273-17277 (2013-10-11)
The nicotinic acetylcholine (ACh) receptor (nAChR) is the principal insecticide target. Nearly half of the insecticides by number and world market value are neonicotinoids acting as nAChR agonists or organophosphorus (OP) and methylcarbamate (MC) acetylcholinesterase (AChE) inhibitors. There was no
John E Casida et al.
Chemico-biological interactions, 203(1), 221-225 (2012-08-29)
The anticholinesterase (antiChE) organophosphorus (OP) and methylcarbamate (MC) insecticides have been used very effectively as contact and systemic plant protectants for seven decades. About 90 of these compounds are still in use - the largest number for any insecticide chemotype
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