319813

Methyl cyanoformate

99%

• 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
• UNSPSC Code: 12352100
• PubChem Substance ID: 24859191
• NACRES: NA.22

Properties

• 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

Description

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.[1][2][3][4]

Safety Information

• Pictograms: GHS02,GHS06
• Signal Word: Danger
• Hazard Statements: H226,H300 + H310 + H330,H315,H319
• Precautionary Statements: P210 - P233 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• 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