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Merck
CN

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:
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

Key Documents

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Product Name

Ethyl cyanoformate, ≥95%

InChI key

MSMGXWFHBSCQFB-UHFFFAOYSA-N

InChI

1S/C4H5NO2/c1-2-7-4(6)3-5/h2H2,1H3

SMILES string

CCOC(=O)C#N

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.)

Quality Level

100

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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.

pictograms

FlameCorrosion
GHS02,GHS05

signalword

Danger

hcodes

H226,H314

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN1445
BCCK4730
STBH9383
STBG1595V
STBD1444V

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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)
Oxidative Cyanation of Tertiary Amines with Ethyl Cyanoformate over a Niobia?Supported Iron?Exchanged Molybdophosphoric Acid Catalyst.
Rao K T V, et al.
ChemCatChem, 4(8), 1173-1178 (2012)
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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