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319813

Methyl cyanoformate

99%

Synonym(s):

2-Methoxy-2-oxoacetonitrile, Cyanoformic acid methyl ester, Mander′s reagent, Methyl carbonocyanidate, [(Cyanocarbonyl)oxy]methane

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About This Item

Linear Formula:
NCCO2CH3
CAS Number:
17640-15-2
Molecular Weight:
85.06
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24859191
EC Number:
241-626-6
Beilstein/REAXYS Number:
1742994
MDL number:
MFCD00013420
Assay:
99%
Form:
liquid
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Quality Segment

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.)

functional group

ester, nitrile

SMILES string

COC(=O)C#N

InChI

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

InChI key

OBWFJXLKRAFEDI-UHFFFAOYSA-N

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

3 - Flammable liquids

WGK

WGK 3

Flash Point (°F)

78.8 °F - closed cup

Flash Point (°C)

26 °C - closed cup

PPE (personal protective equipment)

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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