E18859
Ethyl cyanoformate
99%
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:
Molecular Weight:
99.09
Beilstein:
635955
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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
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Related Categories
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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
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
Flash Point(C)
24 °C
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Customers Also Viewed
N-heterocyclic carbene catalyzed cyanation reaction of carbonyl compounds with ethyl cyanoformate and acetyl cyanide
Zhang J, et al.
Tetrahedron Letters, 52(52), 7153-7156 (2011)
Asymmetric cyanation of activated olefins with ethyl cyanoformate catalyzed by a modular titanium catalyst.
Wang J, et al.
Organic Letters, 12(6), 1280-1283 (2010)
Nickel/Lewis acid-catalyzed cyanoesterification and cyanocarbamoylation of alkynes.
Hirata Y, et al.
Journal of the American Chemical Society, 132(29), 10070-10077 (2010)
DMAP-catalyzed cyanation of aldehydes and ketones with ethyl cyanoformate.
Aoki S, et al.
Tetrahedron Letters, 51(27), 3547-3549 (2010)
Enantioselective cyanoethoxycarbonylation of isatins promoted by a Lewis base?Br?nsted acid cooperative catalyst.
Ogura Y, et al.
Angewandte Chemie (International Edition in English), 52(32), 8299-8303 (2013)
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