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246352

Sigma-Aldrich

Methyl carbamate

98%

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Synonym(s):
Urethylane
Linear Formula:
NH2COOCH3
CAS Number:
Molecular Weight:
75.07
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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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This Item
241989197009696005
Methyl carbamate 98%

Sigma-Aldrich

246352

Methyl carbamate

Ethoxybenzene 99%

Sigma-Aldrich

241989

Ethoxybenzene

form

crystals

form

liquid

form

-

form

powder

bp

176-177 °C (lit.)

bp

169-170 °C (lit.)

bp

-

bp

-

mp

56-58 °C (lit.)

mp

−30 °C (lit.)

mp

110-112 °C (lit.)

mp

56-58 °C (lit.)

solubility

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

solubility

alcohol: freely soluble(lit.), diethyl ether: freely soluble(lit.), water: insoluble(lit.)

solubility

water: soluble 0.7% at 25 °C(lit.), olive oil: soluble 4.8%(lit.), alcohol: freely soluble(lit.), benzene: moderately soluble(lit.), chloroform: moderately soluble(lit.), diethyl ether: freely soluble(lit.), ethyl acetate: freely soluble(lit.), hot water: soluble(lit.)

solubility

-

Application

Methyl carbamate was used in the synthesis of protected aminocyclopropanes.

Pictograms

Exclamation markHealth hazard

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

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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
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
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

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