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Merck

E18425

Ethyl cyanoacetate

≥98%

Synonym(s):

(Ethoxycarbonyl)acetonitrile, 2-Cyanoacetic acid ethyl ester, 3-Ethoxy-3-oxopropanenitrile, Cyanoacetic acid ethyl ester, Cyanoacetic ester, Ethyl α-cyanoacetate, Ethyl 2-cyanoacetate, Ethyl cyanacetate, Malonic acid ethyl ester nitrile

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About This Item

Linear Formula:
NCCH2COOC2H5
CAS Number:
105-56-6
Molecular Weight:
113.11
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24894436
EC Number:
203-309-0
Beilstein/REAXYS Number:
605871
MDL number:
MFCD00001940

Key Documents

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Product Name

Ethyl cyanoacetate, ≥98%

SMILES string

CCOC(=O)CC#N

InChI key

ZIUSEGSNTOUIPT-UHFFFAOYSA-N

InChI

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

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.)

Quality Level

200

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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.

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.

Ethyl cyanoacetate is widely used as a building block in organic synthesis to produce active pharmaceutical ingredients.

Packaging

Packaged in glass bottles

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

230.0 °F

flash_point_c

110 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ1881
MKCJ6602
SHBF9993V
SHBF9992V
SHBF9393V

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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
Mohie E M Zayed et al.
Journal of fluorescence, 27(3), 853-860 (2017-01-23)
4-(2,3,4-trimethoxyphenyl)-8-methoxy-2-oxo-1,2,5,6 tetrahydrobenzo [h] quinoline-3-carbonitrile (TMTQ) dye was synthesized by one-pot multicomponent reactions (MCRs) of 2,3,4 trimethoxybenzaldehyd, ethyl cyanoacetate, 6-methoxy-1,2,3,4-tetrahydro-naphthalin-1-one and ammonium acetate under microwave irradiation. The structures of the synthesized compound was established by spectroscopic (FT-IR
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)
Microwave Enhanced Knoevenagel Condensation of Ethyl Cyanoacetate with Aldehydes.
Kim S-Y, et al.
Synthetic Communications, 27(4), 533-541 (1997)
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)
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