PRODUCTS

ECYA (ETHYL CYANO ACETATE)

EC / List no.: 203-309-0
CAS no.: 105-56-6
Mol. formula: C5H7NO2

ECYA (Ethyl Cyano Acetate) is the ethyl ester of cyanoacetic acid.
ECYA (Ethyl Cyano Acetate) hydrolizes rapidly under neutral and alkaline conditions to cyanoacetic acid and ethanol (and so it does under most physiological and environmental conditions), while in acid pH the half life is considerably longer.
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.

ECYA (Ethyl Cyano Acetate) is a colorless to straw colored liquid with a mild pleasant odor

Uses:
ECYA (Ethyl Cyano Acetate) may be used in the synthesis of ethyl glyoxylate.
ECYA (Ethyl Cyano Acetate) was used to investigate the Knoevenagel condensation reactions in microreactor using zeolite catalysts obtained by grafting amino groups onto NaX and CsNaX zeolites.
Reagent used in labelled pyrimidine and purine synthesis.
ECYA (Ethyl Cyano Acetate) is an ester.
ECYA (Ethyl Cyano Acetate) may be used in the synthesis of ethyl glyoxylate.
ECYA (Ethyl Cyano Acetate) was used to investigate the Knoevenagel condensation reactions in microreactor using zeolite catalysts obtained by grafting amino groups onto NaX and CsNaX zeolites.
Used as a pharmaceutical intermediate, for caffeine and vitamin B, but also for oil-soluble couplers for color films and raw materials for 502 adhesives
Used in organic synthesis of pharmaceuticals and dyes

Industry Uses
- Adhesives and sealant chemicals
- Polymeric colorant
- Solvents (for cleaning and degreasing)

Consumer Uses
- Adhesives and sealants
- Personal care products

General Manufacturing Information
Industry Processing Sectors
- Adhesive manufacturing
- All other basic organic chemical manufacturing
- Wholesale and retail trade

ECYA (Ethyl Cyano Acetate) is the ethyl ester of cyanoacetic acid.
ECYA (Ethyl Cyano Acetate) hydrolyzes rapidly under neutral and alkaline conditions to cyanoacetic acid and ethanol (and so it does under most physiological and environmental conditions), while in acid pH the half life is considerably longer.
ECYA (Ethyl Cyano Acetate) also is likely that unspecific esterases in the body catalyze the hydrolysis to cyanoacetic acid and ethanol, as it has been shown for the structurally related ethyl acetate, which is rapidly hydrolyzed in vitro and in vivo by various esterases to yield ethanol and acetic acid.
Ethanol is a physiological substance that is metabolized via physiological pathways.
Ethanol (CAS. 64-17- 5) was evaluated within the OECD HPV Chemicals Programme.
ECYA (Ethyl Cyano Acetate) can be assumed that for most endpoints cyanoacetic acid will be the common metabolite that determines the toxicity of both substances.
Furthermore the production and use pattern of both, ester and acid, are comparable.
As the acid and the ester have different physical chemical properties due to their chemical nature, effects that are related to the acidity of the acid (e.g. ecotoxicity data, local irritating effects) have to be assessed separately.
The environmental and toxicokinetic distribution can however be expected to range in a similar order of magnitude due to the similar polarity, vapor pressure and log Kow.
The biodegradation behavior is also expected to be comparable as the ester is probably cleaved and the metabolites further degraded.

ECYA (Ethyl Cyano Acetate) is an organic compound that contains a carboxylate ester and a nitrile.
ECYA (Ethyl Cyano Acetate) is a colourless liquid with a pleasant odor.
This material is useful as a starting material for synthesis due to its variety of functional groups and chemical reactivity.

Preparation
ECYA (Ethyl Cyano Acetate) can be prepared by the action of sodium or potassium cyanide on ethyl chloroacetate, and by the action of sodium cyanide on sodium chloroacetate, followed by esterification.

General Description
A colorless liquid.
Denser than water.
Contact may irritate skin, eyes and mucous membranes.
Flash point 210°F.
May be toxic by ingestion.
Used to make other chemicals.

Characteristics of colorless or yellowish liquid. Aromatic odor.
melting point -22.5 ℃
boiling point 208~210 ℃
relative density 1.0560
refractive index 1.4175
flash point 110 ℃
solubility insoluble in water. Miscible with ethanol and ether. Soluble in aqueous ammonia, strong alkali solution.

colorless or yellowish liquid.
Aromatic odor.
The relative density was 1. 0560.
Melting Point -22.5 °c.
Boiling point 208~210 deg C.
Refractive index 4175.
Flash point 110 °c.
Insoluble in water.
Miscible with ethanol and ether.
Soluble in aqueous ammonia, strong alkali solution.

Preparation Method
chloroacetic acid esterification cyanation method esterification of chloroacetic acid and ethanol to generate ethyl chloroacetate, the refined ethyl chloroacetate and sodium cyanide were cyanated to prepare the crude ethyl cyanoacetate, which was then filtered, high quality ethyl cyanoacetate can be obtained by frequent pressure distillation and vacuum distillation.
chloroacetic acid cyanation esterification method to generate chloroacetic acid with soda ash neutralization of sodium chloroacetate, and then with sodium cyanide to sodium cyanoacetate, then with hydrochloric acid to obtain cyanoacetic acid, and finally with ethanol esterification to obtain ethyl cyanoacetate, after filtration, atmospheric distillation, vacuum distillation to obtain the finished product.
cyanoacetic acid esterification method cyanoacetic acid was esterified with ethanol.

raw materials for organic synthesis.
ECYA (Ethyl Cyano Acetate) is used as an intermediate in the synthesis of caffeine and vitamin B6 in medicine.
ECYA (Ethyl Cyano Acetate) is also used as a raw material and analytical reagent for color film oil soluble couplers and synthetic adhesives.

Production
ECYA (Ethyl Cyano Acetate) may be prepared in various ways:

Kolbe nitrile synthesis using ethyl chloroacetate and sodium cyanide.
Fischer esterification of cyanoacetic acid with ethanol in the presence of a strong mineral acids (e.g. concentrated sulfuric acid).
The cyanoacetic acid can be prepared via Kolbe nitrile synthesis using sodium chloroacetate and sodium cyanide.
Reaction of the sodium cyanoacetate with ethyl bromide in an aqueous–organic two-phase system in the presence of a phase transfer catalyst.
Oxidation of 3-ethoxypropionitrile, an ether, with oxygen under pressure in the presence of cobalt(II) acetate tetrahydrate as catalyst and N-hydroxyphthalimide as a radical generator.

Properties
Physical properties
The vapor pressure follows the Antoine equation log10(P) = A−(B/(T+C)) (P in bar, T in K) with A = 7.46724, B = 3693.663 and C = 16.138 in the temperature range from 341 to 479 K Two polymorphic forms occur.
Below −111 °C, the crystal form II is dominant.
Above this temperature, the crystal form I is formed which melts at −22 °C.[8] The heat capacity at 25 °C is 220.22 J K−1 mol−1.

Chemical properties
With its three different reactive centers—nitrile, ester, acidic methylene site—ethyl cyanoacetate is a versatile synthetic building block for a variety of functional and pharmacologically active substances.
ECYA (Ethyl Cyano Acetate) contains an acidic methylene group, flanked by both the nitrile and carbonyl, and so can be used in condensation reactions like the Knoevenagel condensation or the Michael addition.
This reactivity is similar to that of esters of malonic acid.
As an example of reactivity at the nitrile, diethyl malonate is obtained from cyanoacetic acid ethyl ester by reaction with ethanol in the presence of strong acids.
Heating in the presence of sodium ethoxide forms the dimeric 3-amino-2-cyano-2-pentendiaciddiethylester.

Uses:
Due to its functionality cyanoacetate reacts:

At the nitrile group in various ways:
Hydrogenation leads to the β-amino acid β-alanine
Nucleophilic attack at the carbon, as a step in the synthesis of many heterocycles (see below) and other products
As a safe cyanide-donor reagent
Nucleophilic attack at the ester group, as part of acyl substitution: reaction with ammonia leads to cyanoacetamide, which can be converted by dehydration with PCl5 or POCl3 to malononitrile.
Via the acidic methylene group as a nucleophile
ECYA (Ethyl Cyano Acetate) is a building block for the synthesis of heterocycles which are used for example as drugs:

Allopurinol, used for the treatment of chronic gout, can be synthesized starting with a Knoevenagel condensation with triethyl orthoformate, the condensation product is cyclized with hydrazine to give a substituted pyrazole and subsequently with formamide to allopurinol, a substituted pyrazolo-pyrimidine.
The purine derivatives theophylline, caffeine and uric acid are synthetically accessible from ethyl cyanoacetate and N,N'-dimethylurea.
The pteridine derivative folic acid is assigned to the vitamin B complex; ethyl cyanoacetate and guanidine can be used as starting material in a multi-stage convergent synthesis.
The pyrrole ethosuximide is used to treat epilepsy, it can be obtained from ethyl cyanoacetate and butanone in a multistep synthesis.
The pyrimidine derivative trimethoprim is used as co-trimoxazole in fixed combination with sulfamethoxazole used as bacteriostatic agent and is synthesized from ethyl cyanoacetate and 3,4,5-trimethoxybenzaldehyde or its benzyl chloride.
Also many other functional heterocycles are in good yields accessible from ethyl cyanoacetate, such as 3-substituted coumarin derivatives.

Non-cyclic products from this starting material include:

The anticonvulsant valproic acid
Ethyl cyanoacrylate, used as superglue, via reaction with formaldehyde
ECYA (Ethyl Cyano Acetate) is also used to prepare 3,3-diphenylpropan-1-amine, which is the precursor used in the synthesis of Prenylamine & Droprenilamine.

ECYA (Ethyl Cyano Acetate) appears as a colorless liquid.
Denser than water.
Contact may irritate skin, eyes and mucous membranes.
May be toxic by ingestion.
Used to make other chemicals.

ECYA (Ethyl Cyano Acetate) is a building block for the synthesis of heterocycles and are are used as drugs.
ECYA (Ethyl Cyano Acetate) is also used as Pharmaceutical intermediates, or Oil soluble couplers of film raw material .
ECYA (Ethyl Cyano Acetate) is also used as a reagent in labelled pyrimidine and purine synthesis.
ECYA (Ethyl Cyano Acetate) is used as an intermediate of fine chemicals such as medicine and dyestuff.

This Thermo Scientific brand product was originally part of the Alfa Aesar product portfolio.
Some documentation and label information may refer to the legacy brand.
The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific.

Applications
ECYA (Ethyl Cyano Acetate) is a building block for the synthesis of heterocycles and are are used as drugs.
ECYA (Ethyl Cyano Acetate) is also used as Pharmaceutical intermediates, or Oil soluble couplers of film raw material .
ECYA (Ethyl Cyano Acetate) is also used as a reagent in labelled pyrimidine and purine synthesis.
ECYA (Ethyl Cyano Acetate) is used as an intermediate of fine chemicals such as medicine and dyestuff.

Solubility
ECYA (Ethyl Cyano Acetate) is slightly soluble in water. Mostly soluble in organic solvents such as chloroform, ethyl acetate.

About ECYA (Ethyl Cyano Acetate)
Helpful information
ECYA (Ethyl Cyano Acetate) is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 tonnes per annum.

ECYA (Ethyl Cyano Acetate) is used by consumers, by professional workers (widespread uses), in formulation or re-packing and at industrial sites.

Consumer Uses
ECYA (Ethyl Cyano Acetate) is used in the following products: adhesives and sealants, coating products and fillers, putties, plasters, modelling clay.
Other release to the environment of ECYA (Ethyl Cyano Acetate) is likely to occur from: indoor use as processing aid and outdoor use as processing aid.
Article service life
ECHA has no public registered data on the routes by which ECYA (Ethyl Cyano Acetate) is most likely to be released to the environment. ECHA has no public registered data indicating whether or into which articles the substance might have been processed.

Widespread uses by professional workers
ECYA (Ethyl Cyano Acetate) is used in the following products: adhesives and sealants.
ECHA has no public registered data on the types of manufacture using ECYA (Ethyl Cyano Acetate) . Other release to the environment of ECYA (Ethyl Cyano Acetate) is likely to occur from: indoor use as processing aid and outdoor use as processing aid.
Formulation or re-packing
ECYA (Ethyl Cyano Acetate) is used in the following products: adhesives and sealants and washing & cleaning products. Release to the environment of ECYA (Ethyl Cyano Acetate) can occur from industrial use: formulation of mixtures.

Uses at industrial sites
ECYA (Ethyl Cyano Acetate) is used in the following products: adhesives and sealants and laboratory chemicals.
ECYA (Ethyl Cyano Acetate) has an industrial use resulting in manufacture of another substance (use of intermediates).
ECYA (Ethyl Cyano Acetate) is used for the manufacture of: chemicals.
Release to the environment of ECYA (Ethyl Cyano Acetate) can occur from industrial use: in processing aids at industrial sites and as an intermediate step in further manufacturing of another substance (use of intermediates).
Manufacture
ECHA has no public registered data on the routes by which ECYA (Ethyl Cyano Acetate) is most likely to be released to the environment.

IUPAC NAMES:
Acetic acid, 2-cyano-, ethyl ester
ECYA
Ethyl 2-cyanoacetate
ethyl 2-cyanoacetate
Ethyl Cyanoacetate
ECYA (Ethyl Cyano Acetate)
ethyl cyanoacetate
ethyl cyanoacetate
ethyl cyanoacétate

SYNONYMS:
2-cyano-aceticacidethylester
Acetic acid,2-cyano-, ethyl ester
Aceticacid,cyano-,ethylester
Cyanacetate ethyle
cyanacetateethyle
ethylcyanacetate
Ethylcyanoacetat
Ethylester kyseliny kyanoctove
ethylesterkyselinykyanoctove
NCCH2COOC2H5
USAF kf-25
usafkf-25
ETHYL CYANOACETATE extrapure
CL079
2-cyanobutanoate
Ethyl cyanoacetate, 98+% 250GR
ETHYL CYANOACETATE FOR SYNTHESIS
2-Ethenylpyrazine
3-Oxo-3-ethoxypropanenitrile
Cyanoacetic acid ethyl
Ethoxycarbonylcyanomethane
Ethyl cyanoacetate ,99.5%
Ethyl cyanoacetate ,70%
Ethyl Cyanoacetate (Shanxi)
Pregabalin Impurity 39 (Ethyl cyanoacetate)
Cyanessigester
cyanoacetated’ethyle
Cyanoacetic ester
cyano-aceticaciethylester
cyanoaceticester
Cyanoessigsαureethylester
Estere cianoacetico
esterecianoacetico
ethanoicacid,cyano-,ethylester
Ethyl cyanacetate
Ethyl ester of cyanoacetic acid
ECYA
CYANOACETIC ACID ETHYL ESTER
ETHYL CYANOACETATE
ETHYL CYANOETHANOATE
ETHYL 2-CYANOACETATE
AKOS BBS-00004275
ETHYLE CYANACETATE
MALONIC ACID ETHYL ESTER NITRILE
malonic ethyl ester nitrile
ETHYL CYANOACETATE, 98+%
ETHYL CYANOACETATE, STANDARD FOR GC
ETHYL CYANOACETATE, 99+%
Ethyl Cyano Acetate 99, Benzene Free
EthylCynoacetate
ethyl cyanocaetate
Ethylcyanacetat
Ethyl Cyanoacetate >
ETHYL CYANOACETATE 105-56-6
Ethyl cyanoacetate ISO 9001：2015 REACH
105-56-6 [RN]
203-309-0 [EINECS]
Acetic acid, 2-cyano-, ethyl ester [ACD/Index Name]
acetic acid, cyano-, ethyl ester
Cyanoacétate d'éthyle [French] [ACD/IUPAC Name]
Cyanoacetic acid ethyl ester
Cyano-acetic acid ethyl ester
ethyl 2-cyanoacetate
Ethyl cyanoacetate [ACD/IUPAC Name] [Wiki]
ethyl cyanoethanoate
ethyl α-cyanoacetate
Ethyl-cyanacetat [German] [ACD/IUPAC Name]
MFCD00001940 [MDL number]
17341-93-4 [RN]
27924-04-5 [RN]
2999-46-4 [RN]
2-cyanoacetic acid ethyl ester
698387-41-6 [RN]
80058-84-0 [RN]
930-68-7 [RN]
Acetic acid,2-cyano-, ethyl ester
ACETIC ACID,CYANO,ETHYL ESTER
Cyanacetate ethyle
Cyanoacetic acid, ethyl ester
Cyanoacetic ester
CyanoaceticAcidEthylEster
Estere cianoacetico
ethyl 2-cyanoethanoate
ethyl cyanacetate
ETHYL CYANO ACETATE
Ethyl cyanoacetic acid
ethyl2-cyanoacetate
Ethylcyanoacetate
Ethylester kyseliny kyanoctove [Czech]
Ethylester kyseliny kyanoctove
Malonic acid, ethyl ester nitrile
NCCH2COOC2H5
STR00038
WLN: NC1VO2