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Ethyl cyanoacetate 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 ...
The compound 2-octyl cyanoacrylate degrades much more slowly due to its longer organic backbone (series of covalently bonded carbon molecules) and the adhesive does not reach the threshold of tissue toxicity. Due to the toxicity issues of ethyl cyanoacrylate, the use of 2-octyl cyanoacrylate for sutures is preferred. [33]
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.
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 ...
This reaction is important in the history of organic chemistry because it helped prove the structure of ethers. The general reaction mechanism is as follows: [3] An example is the reaction of sodium ethoxide with chloroethane to form diethyl ether and sodium chloride: C 2 H 5 Cl + C 2 H 5 ONa → C 2 H 5 OC 2 H 5 + NaCl
One can subdivide chemical compounds into two main groups: molecules, which includes most organic, polyatomic gases, and organometallic compounds, and nonmolecular species, which includes most purely inorganic compounds. The structures of many reagents are often misunderstood because simplified formulas are presented in reaction schemes whereas ...
In this reaction the carbonyl group is an aldehyde or a ketone. The catalyst is usually a weakly basic amine. The active hydrogen component has the forms: [3] Z−CH 2 −Z or Z−CHR−Z for instance diethyl malonate, Meldrum's acid, ethyl acetoacetate or malonic acid, or cyanoacetic acid. [1] Z−CHRR', for instance nitromethane.
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 ...