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Merck

E18425

Ethyl cyanoacetate

≥98%

Synonyme(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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A propos de cet article

Formule linéaire :
NCCH2COOC2H5
Numéro CAS:
105-56-6
Poids moléculaire :
113.11
Beilstein:
605871
Numéro CE :
203-309-0
Numéro MDL:
MFCD00001940
Code UNSPSC :
12352100
ID de substance PubChem :
24894436
Nomenclature NACRES :
NA.22

Principaux documents

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Densité de vapeur

3.9 (vs air)

Niveau de qualité

200

Pression de vapeur

1 mmHg ( 67.8 °C)

Essai

≥98%

Forme

liquid

Indice de réfraction

n20/D 1.418 (lit.)

pb

208-210 °C (lit.)

Pf

−22 °C (lit.)

Densité

1.063 g/mL at 25 °C (lit.)

Chaîne SMILES 

CCOC(=O)CC#N

InChI

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

Clé InChI

ZIUSEGSNTOUIPT-UHFFFAOYSA-N

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Cet article
10842154305528440
Ethyl cyanoacetate ≥98%

Sigma-Aldrich

E18425

Ethyl cyanoacetate

Methyl cyanoacetate 99%

Sigma-Aldrich

108421

Methyl cyanoacetate

Ethyl 1-cyano-1-cyclopropanecarboxylate 96%

Sigma-Aldrich

543055

Ethyl 1-cyano-1-cyclopropanecarboxylate

tert-Butyl cyanoacetate ≥97.0% (GC)

Sigma-Aldrich

28440

tert-Butyl cyanoacetate

assay

≥98%

assay

99%

assay

96%

assay

≥97.0% (GC)

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

form

liquid

form

-

form

-

form

-

refractive index

n20/D 1.418 (lit.)

refractive index

n20/D 1.417 (lit.)

refractive index

n20/D 1.445 (lit.)

refractive index

n20/D 1.420

mp

−22 °C (lit.)

mp

−13 °C (lit.)

mp

-

mp

-

bp

208-210 °C (lit.)

bp

204-207 °C (lit.)

bp

217 °C (lit.)

bp

40-42 °C/0.1 mmHg (lit.)

Description générale

Ethyl cyanoacetate is an ester. Knoevenagel condensation of ethyl cyanoacetate with aldehyde is reported.[1] 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.[2][3]

Application

Ethyl cyanoacetate may be used in the synthesis of ethyl glyoxylate.[4] It was used to investigate the Knoevenagel condensation reactions in microreactor using zeolite catalysts obtained by grafting amino groups onto NaX and CsNaX zeolites.[5]

Conditionnement

Packaged in glass bottles

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H319

Classification des risques

Eye Irrit. 2

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

230.0 °F

Point d'éclair (°C)

110 °C

Équipement de protection individuelle

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

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Certificats d'analyse (COA)

Lot/Batch Number
MKCX8763
MKCT0403
MKCQ1881
MKCJ6602
SHBF9993V

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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
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)
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
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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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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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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