cyanoacetic

Cyanoacetic refers to compounds derived from 2-cyanoacetic acid, the parent molecule with the formula NC-CH2-CO2H, and to its derivatives such as cyanoacetic esters. The molecule features a nitrile group adjacent to a carboxyl group, making it a versatile bifunctional building block in organic synthesis. The methylene hydrogen is relatively acidic, allowing formation of the cyanoacetate anion for various condensation and enolate reactions. The esters of cyanoacetic acid, known as cyanoacrylates, are especially reactive.

Production and chemistry: Industrially, cyanoacetic acid is typically prepared from ethyl cyanoacetate, which is hydrolyzed to the acid and then esterified or converted into cyanoacrylate esters. Substituted cyanoacetic derivatives arise by alkylation at the methylene position or by condensations with aldehydes and ketones to form cyanoacrylates and related compounds. These processes provide a range of reagents used in further chemical synthesis.

Applications: The most prominent use of cyanoacetic derivatives is as precursors to cyanoacrylate adhesives, commonly known as superglues. Ethyl and methyl cyanoacrylates polymerize rapidly in the presence of moisture to form strong bonds with many substrates. Beyond adhesives, cyanoacetic acid and its esters are valued as versatile building blocks for the synthesis of beta-keto esters, heterocycles, and various pharmaceutical intermediates.

Safety and handling: Cyanoacetic acids and their esters are irritants and should be handled with appropriate safety measures. They can react exothermically and may pose hazards if heated or burned; standard laboratory storage and handling guidelines should be followed.