E18859
Ethyl cyanoformate
≥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:
Molecular Weight:
99.09
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
210-797-9
Beilstein/REAXYS Number:
635955
MDL number:
Assay:
≥95%
Form:
liquid
Quality Segment
assay
≥95%
form
liquid
refractive index
n
bp
115-116 °C (lit.)
density
1.003 g/mL at 25 °C (lit.)
functional group
ester, nitrile
SMILES string
CCOC(=O)C#N
InChI
1S/C4H5NO2/c1-2-7-4(6)3-5/h2H2,1H3
InChI key
MSMGXWFHBSCQFB-UHFFFAOYSA-N
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.
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
75.2 °F - closed cup
flash_point_c
24 °C - closed cup
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
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