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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
Beilstein:
605871
EC Number:
203-309-0
MDL number:
MFCD00001940
UNSPSC Code:
12352100
PubChem Substance ID:
24894436
NACRES:
NA.22

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vapor density

3.9 (vs air)

Quality Level

200

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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This Item
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.)

General description

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]

Packaging

Packaged in glass bottles

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX8763
MKCT0403
MKCQ1881
MKCJ6602
SHBF9993V

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Microwave Enhanced Knoevenagel Condensation of Ethyl Cyanoacetate with Aldehydes.
Kim S-Y, et al.
Synthetic Communications, 27(4), 533-541 (1997)
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
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
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
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)
View All Related Papers

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.

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    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?

    1 answer

    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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