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Ethyl cyanoacetate is an organic compound that contains a carboxylate ester and a nitrile. It is a colourless [ 1 ] 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.
In its largest scale application, cyanoacetic acid is first esterified to give ethyl cyanoacetate. Condensation of that ester with formaldehyde gives ethyl cyanoacrylate , which used as superglue. As of 2007, more than 10,000 tons of cyanoacetic acid were produced annually.
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Ethyl cyanoacrylate is prepared by the condensation of formaldehyde with ethyl cyanoacetate: NCCH 2 CO 2 C 2 H 5 + CH 2 O → H 2 C=C(CN)CO 2 C 2 H 5 + H 2 O. This exothermic reaction affords the polymer, which is subsequently sintered, thermally "cracked" to give the monomer. Alternatively, it can be prepared by the ethoxycarbonylation of ...
Ethyl cyanohydroxyiminoacetate (oxyma) is the oxime of ethyl cyanoacetate and finds use as an additive for carbodiimides, such as dicyclohexylcarbodiimide (DCC) in peptide synthesis. It acts as a neutralizing reagent for the basicity or nucleophilicity of the DCC due to its pronounced acidity ( pKa 4.60) and suppresses base catalyzed side ...
Cyanation of ketones or aldehydes yields the corresponding cyanohydrins, which can be done directly with the cyanide ion (the cyanohydrin reaction) or by using bisulfite, followed by displacement of sulfite: [3] [4] Cyanation of aldehyde with bisulfite. A related reaction is hydrocyanation, which installs the elements of H-CN.
The Kolbe nitrile synthesis is a method for the preparation of alkyl nitriles by reaction of the corresponding alkyl halide with a metal cyanide. [1] A side product for this reaction is the formation of an isonitrile because the cyanide ion is an ambident nucleophile. The reaction is named after Hermann Kolbe.
An example involves the conversion of the ethyl ester of 5-bromovaleric acid to the iodide: [4] EtO 2 C(CH 2) 4 Br + NaI → EtO 2 C(CH 2) 4 I + NaBr. Potassium fluoride is used for the conversion of chlorocarbons into fluorocarbons. [5] Such reactions usually employ polar solvents such as dimethyl formamide, ethylene glycol, and dimethyl ...