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Merck

E18425

Sigma-Aldrich

Ethylcyanoacetat

≥98%

Synonym(e):

(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

Lineare Formel:
NCCH2COOC2H5
CAS-Nummer:
Molekulargewicht:
113.11
Beilstein:
605871
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352100
PubChem Substanz-ID:
NACRES:
NA.22

Dampfdichte

3.9 (vs air)

Qualitätsniveau

Dampfdruck

1 mmHg ( 67.8 °C)

Assay

≥98%

Form

liquid

Brechungsindex

n20/D 1.418 (lit.)

bp

208-210 °C (lit.)

mp (Schmelzpunkt)

−22 °C (lit.)

Dichte

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

InChIKey

ZIUSEGSNTOUIPT-UHFFFAOYSA-N

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Allgemeine Beschreibung

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.

Anwendung

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.

Verpackung

Packaged in glass bottles

Piktogramme

Exclamation mark

Signalwort

Warning

H-Sätze

Gefahreneinstufungen

Eye Irrit. 2

Lagerklassenschlüssel

10 - Combustible liquids

WGK

WGK 1

Flammpunkt (°F)

230.0 °F

Flammpunkt (°C)

110 °C

Persönliche Schutzausrüstung

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


Analysenzertifikate (COA)

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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)

Artikel

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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