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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.
Well measured values are typically within 0.1 units of each other. Data presented here were taken at 25 °C in water. [7] [86] More values can be found in the Thermodynamics section, above. A table of pK a of carbon acids, measured in DMSO, can be found on the page on carbanions.
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 ...
Methoxypropylamino cyclohexenylidene ethoxyethylcyanoacetate is an organic compound used in sunscreens to absorb UVA radiation.It is marketed as Mexoryl 400 by L'Oréal. ...
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The σ values displayed in the Table above reveal certain substituent effects. With ρ = 1, the group of substituents with increasing positive values—notably cyano and nitro —cause the equilibrium constant to increase compared to the hydrogen reference, meaning that the acidity of the carboxylic acid (depicted on the left of the equation ...