Cyanoacetic acid ethyl ester

Ethyl (l-methyl-5(l)-butenyl)cyanoacetic acid ethyl ester... 

SYNS CYANACETATE ETHYLE (GERMAN) CYANOACETIC ACID ETHYL ESTER CYANOACETIC ESTER ESTERE CIANOACETICO ETHYL CYANOACETATE ETHYL CYANOETHANOATE ETHYLESTER KYSEUNY KYANOCTOVE MALONIC ACID ETHYL ESTER NITRILE USAF KF-25... 

Pyridinitrile is prepared by the reaction of cyanoacetic acid ethyl ester (3) with ammonia, followed by the coupling of two molecules of the cyanoacetic amide (4) formed with benzaldehyde (5) and by the chlorination of the product, 3,5-dicyano-... 

Beilstein Handbook Reference) Acetic acid, cyano-, ethyl ester AI3-19027 BRN 0605871 Cyanacetate ethyle Cyanoacetic acid ethyl ester Cyanoacetic ester EINECS 203-309-0 Estere cianoacetico Ethyl cyanacetate Ethyl cyanoacetate Ethyl cyanoethanoate Ethylester kyseliny kyanoctove HSDB 2769 Malonic acid ethyl ester nitrile NSC 8844 UN2666 USAF KF-25. Liquid mp = -22.5° bp = 205° d = 1.0654 very soluble in EtOH, Et20. 

Cyanoacetic acid ethyl ester, technical grade 20 C 20 C... 

Cycloheptanone Cyanoacetic acid methyl ester Ethyl bromide Hydrogen chloride... 

Ethyl thioglycolate and ethyl cyanoacetate are first reacted in the presence of sodium ethylate to give 4-oxo-thiazolidin-2-ylideneacetic acid ethyl ester. That is reacted with diethyl sulfate and then with piperidine to give piprozolin. 

Polymerizable 3-(2-cyano-acryloyloxy)-butyric acid ethyl ester has been prepared in a two-step process using 3-hydroxybutyrate and cyanoacetic acid followed by treatment with formaldehyde. This and related alkyl ester cx-cyanoacrylate monomers are useful as tissue adhesives/sealants in surgical and related medical applications. 

The moisture- and air-stable ionic liquids, l-butyl-3-methylimidazolium tetra-lluoroborate [bmim]BF and l-butyl-3-methylimidazolium hexafluorophosphate [bmim]PFg, were used as green recyclable alternatives to volatile organic solvents for the ethylenediaimnonium diacetate-catalyzed Knoevenagel condensation between aldehydes or ketones with active methylene compounds. As described by Su et al. [57], the ionic hquids containing a catalyst were recycled several times without decrease in yields and reaction rates. In the case of 2-hydroxybenzaldehyde, the reactions led to the formation of 3-substituted coumarin derivatives in high yields of up to 95% (Scheme 17.11). When ethyl cyanoacetate was used, 2-imino-27f-l-benzopyran-3-carboxyhc acid ethyl ester was formed. 

Ethyl Cyanoacetate. Cyaitoacetic acid ethyl estert cyanoacetic ester ethyl cyanoethanoate malonic acid ethyl ester nitrile. CsH,N02 mol wt 113.12. C 53.09%. H 6.24%, N 12.39%, O 28.29%. CNCH2COOC2HS. Made by the interaction of sodium cyanide and chloroacetic acid and subsequent esterification of the cyanoacetic acid formed Kob -ler, Allen. Org. Syn. 3, 53 (1923) Inglis, ibid. 8, 74 (1928). 

Ethyl cyanoacetate added with cooling to benzalmethylamine in ether, and allowed to stand 24 hrs. at room temp. l,3-diphenyl-2,4-dicyanocyclobutane-2,4-dicarboxylic acid ethyl ester methylamide. Y 78%. F. e. s. H. Bohme and S. Ebel, B. 98, 1819 (1965). 

A microfluidic reaction system has also been used for the production of prodrugs. A multichannel membrane microreactor was fabricated and tested for Knoevenagel condensation of benzaldehyde and ethyl cyanoacetate to produce a-cyanocinnamic acid ethyl ester, a known intermediate for the production of an antihypertensive drug [9]. Knoevenagel condensations of carbonylic coiiqtounds and malonic esters yield several important key products such as nitriles used in anionic polymerization, and the a,p-unsaturated ester intermediates employed in the synthesis of several therapeutic drugs that include niphendip-ine and nitrendipine. Unlike most condensation reactions. 

The methyl and ethyl esters of cyanoacetic acid are slightly soluble ia water but are completely miscible ia most common organic solvents including aromatic hydrocarbons. The esters, like the parent acid, are highly reactive, particularly ia reactions involving the central carbon atom however, the esters tend not to decarboxylate. They are prepared by esterification of cyanoacetic acid and are used principally as chemical iatermediates. 

Table 11. Some Physical Properties of Cyanoacetic Acid and Methyl and Ethyl Esters ...

Cyanoacetic acid, NCCH2COOH Methyl ester, NCCH2COOCH3 Ethyl ester, NCCH2COOC2H3... 

Physical Properties. The physical properties of cyanoacetic acid [372-09-8] NM7—CH2COOH (28) ate summarized in Table 4. The industrially most important esters ate methyl cyanoacetate [105-34-0] and ethyl cyanoacetate [105-56-6]. Both esters ate miscible with alcohol and ether and immiscible with water. 

Cyclobutanedicarboxylic acid has been prepared by hydrolysis of the ethyl ester,1 or of the half nitrile, 1-cyano-l-car-boxycyclobutane.2 The ethyl ester has been prepared by condensation of ethyl malonate with trimethylene bromide1 or chloro-bromide.3 The half nitrile has been prepared by condensation of trimethylene bromide with ethyl cyanoacetate followed by hydrolysis of the ester to the acid.2... 

Cyanoacetic acid, 2 138, 139 and esters, 2 7 244-245 Cyanoacrylate adhesives, 2 539-540 Cyanoacrylate vapors, 22 102 Cyanobacteria, in nitrogen fixation, 2 7 302 Cyanobacterial associations, in nitrogen fixation, 27 299-300 Cyanocobalamin, 7 238 25 803-804 Cyanoethene. See Acrylonitrile (AN) l-Cyanoethyl-2-ethyl-4-methylimidazole (2EMZ-CN) curing catalyst, 20 17 2V-Cyanoethylated toluenediamines, 25 197... 

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