Merck
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E18425

Sigma-Aldrich

Ethyl cyanoacetate

≥98%

Linear Formula:
NCCH2COOC2H5
CAS Number:
Molecular Weight:
113.11
Beilstein:
605871
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

vapor density

3.9 (vs air)

vapor pressure

1 mmHg ( 67.8 °C)

assay

≥98%

form

liquid

refractive index

n20/D 1.418 (lit.)

bp

208-210 °C (lit.)

mp

−22 °C (lit.)

density

1.063 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)CC#N

InChI

1S/C5H7NO2/c1-2-8-5(7)3-4-6/h2-3H2,1H3

InChI key

ZIUSEGSNTOUIPT-UHFFFAOYSA-N

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General description

Ethyl cyanoacetate is an ester. Knoevenagel condensation of ethyl cyanoacetate with aldehyde is reported. Microwave enhanced Knoevenegal condensation reaction of ethyl cyanoacetate with an aldehyde, P2O5, piperidine and chlorobenzene is reported.

Application

Ethyl cyanoacetate may be used in the synthesis of ethyl glyoxylate. It was used to investigate the Knoevenagel condensation reactions in microreactor using zeolite catalysts obtained by grafting amino groups onto NaX and CsNaX zeolites.

Packaging

1 kg in glass bottle
5, 250 g in glass bottle
Packaged in glass bottles

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

230.0 °F

Flash Point(C)

110 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

The Knoevenagel condensation of aromatic aldehydes with malononitrile or ethyl cyanoacetate in the presence of CTMAB in water.
Wang S, et al.
Synthetic Communications, 31(5), 673-677 (2001)
Yuya Oka et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 23(39), 9362-9368 (2017-05-18)
Mesoporous basic Mg-Al mixed metal oxides (MMOs) with a high surface area and large pore size have been prepared through the assembly of monodispersed layered double hydroxide nanoparticles (LDHNPs) with block copolymer templates. The particle sizes of the LDHNPs were
Microwave Enhanced Knoevenagel Condensation of Ethyl Cyanoacetate with Aldehydes.
Kim S-Y, et al.
Synthetic Communications, 27(4), 533-541 (1997)
Electrogenerated bases VII. Novel syntheses of ethyl glyoxalate and diethyl ketomalonate via electrogenerated superoxide.
Sugawara M and Baizer MM.
Tetrahedron Letters, 24(22), 2223-2226 (1983)
Korany A Ali et al.
Mini reviews in medicinal chemistry, 18(8), 717-727 (2017-04-27)
In this study, synthesis, molecular docking and anticancer screening of new series of substituted heterocycles with trimethoxy phenyl scaffold as Combretastatin analogues were described. Substituted pyridines were synthesized via the reaction of (E)-3-(dimethylamino)-1-(3,4,5- trimethoxyphenyl)prop-2-en-1-one (2) with active methylene reagents. Substituted

Articles

Knoevenagel Condensation Reaction

Knoevenagel Condensation is an organic reaction named after Emil Knoevenagel. It is a classic C-C bond formation reaction and a modification of the Aldol Condensation.

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