E18859

Ethyl cyanoformate

99%

• Synonym(s): 2-Ethoxy-2-oxoacetonitrile, Cyanocarbonyloxyethane, Cyanoformic acid ethyl ester, Ethoxycarbonyl cyanide, Ethyl carbonocyanidate
• Linear Formula: NCCO₂C₂H₅
• CAS Number: 623-49-4
• Molecular Weight: 99.09
• Beilstein: 635955
• EC Number: 210-797-9
• MDL number: MFCD00001836
• UNSPSC Code: 12352100
• PubChem Substance ID: 24894440
• NACRES: NA.22

Properties

• Quality Level: 100
• Assay: 99%
• form: liquid
• refractive index: n20/D 1.381 (lit.)
• bp: 115-116 °C (lit.)
• density: 1.003 g/mL at 25 °C (lit.)
• SMILES string: CCOC(=O)C#N
• InChI: 1S/C4H5NO2/c1-2-7-4(6)3-5/h2H2,1H3
• InChI key: MSMGXWFHBSCQFB-UHFFFAOYSA-N

Description

Application

Ethyl cyanoformate can be used as a cyanide source for the cyanation of:

• Activated olefins in the presence of a titanium catalyst.
• Carbonyl compounds catalyzed by 4-dimethylaminopyridine (DMAP) to yield corresponding cyanohydrin carbonates under metal-free and solvent-free conditions.
• Aldehydes and 2,2,2-trifluoroacetophenone catalyzed by N-heterocyclic carbene (NHC) to yield corresponding cyanohydrins ethyl carbonates.

Ethyl cyanoformate is a general cyanating agent. It can be used in the nucleophilic addition of cyanide to carbonyl compounds, oxidative cyanation of tertiary amines and in the synthesis of β-cyano-substituted acrylates from alkynes.

Safety Information

• Pictograms: GHS02,GHS05
• Signal Word: Danger
• Hazard Statements: H226,H314
• Precautionary Statements: P210 - P280 - P303 + P361 + P353 - P305 + P351 + P338 + P310
• Hazard Classifications: Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 3
• Flash Point(F): 75.2 °F - closed cup
• Flash Point(C): 24 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves