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Sigma-Aldrich

Methyl cyanoformate

99%

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Synonym(s):
2-Methoxy-2-oxoacetonitrile, Cyanoformic acid methyl ester, Mander′s reagent, Methyl carbonocyanidate, [(Cyanocarbonyl)oxy]methane
Linear Formula:
NCCO2CH3
CAS Number:
17640-15-2
Molecular Weight:
85.06
Beilstein:
1742994
EC Number:
241-626-6
MDL number:
MFCD00013420
PubChem Substance ID:
24859191
NACRES:
NA.22

Assay

99%

form

liquid

refractive index

n20/D 1.374 (lit.)

bp

100-101 °C (lit.)

density

1.072 g/mL at 25 °C (lit.)

SMILES string

COC(=O)C#N

InChI

1S/C3H3NO2/c1-6-3(5)2-4/h1H3

InChI key

OBWFJXLKRAFEDI-UHFFFAOYSA-N

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General description

Methyl cyanoformate is an organic compound that is commonly used as a source of the methoxycarbonyl group in organic synthesis. It is most frequently used as a reagent to synthesize regioselective β-keto esters via C-acylation of lithium enolates. In comparison with more traditional reagents such as acyl halides, anhydrides, and carbon dioxide, it is regarded as a superior acylating agent.

Application

Selective acylating reagent.

Pictograms

FlameSkull and crossbones
GHS02,GHS06

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

78.8 °F - closed cup

Flash Point(C)

26 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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Tetrahedron Letters, 34, 8553-8553 (1993)
D L Selwood et al.
Journal of medicinal chemistry, 36(23), 3503-3510 (1993-11-12)
A variety of isosteres of the DNA polymerase inhibitor aphidicolin were synthesized as potential antiherpes agents. Modeling studies indicated that the bicyclooctane C, D rings of aphidicolin could be replaced by an aromatic moiety while maintaining the spatial arrangement of
Tetrahedron, 48, 7979-7979 (1992)
Aldrichimica Acta, 20, 53-53 (1987)

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