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E18859

Ethyl cyanoformate

Name: Ethyl cyanoformate
Brand: ALDRICH

≥95%

Synonym(s):

2-Ethoxy-2-oxoacetonitrile, Cyanocarbonyloxyethane, Cyanoformic acid ethyl ester, Ethoxycarbonyl cyanide, Ethyl carbonocyanidate

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About This Item

Linear Formula:

NCCO₂C₂H₅

CAS Number:

623-49-4

Molecular Weight:

99.09

UNSPSC Code:

12352100

NACRES:

NA.22

PubChem Substance ID:

24894440

EC Number:

210-797-9

Beilstein/REAXYS Number:

635955

MDL number:

MFCD00001836

Assay:

≥95%

Form:

liquid

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Properties

Quality Level

100

assay

≥95%

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.