cyanoethyl

Cyanoethyl refers to a cyanoethyl substituent, typically a three-carbon chain with a terminal nitrile group, commonly represented as -CH2-CH2-CN. This group is usually attached to a parent molecule through the first methylene carbon, giving an O- or N- linkage in many derivatives. The nitrile functionality imparts polarity and specific reactivity that is exploited in various areas of organic and polymer chemistry.

One prominent use is as a protective group in nucleotide chemistry. The 2-cyanoethyl protecting group is used on phosphate triesters during the chemical synthesis of DNA and RNA. In this context, phosphate linkages are temporarily masked as O-CH2-CH2-CN esters, which can be removed by base during final deprotection to yield the native phosphate.

Cyanoethyl groups are also involved in cellulose chemistry. Cyanoethyl cellulose is formed by etherification of cellulose with acrylonitrile, introducing cyanoethyl side chains onto the cellulose backbone. This derivative can act as a thickener or rheology modifier and can be further hydrolyzed or chemically transformed, for example to carboxyethyl cellulose, altering solubility and charge properties.

In addition to these applications, cyanoethyl groups may appear as substituents in various organic and polymeric systems where their nitrile functionality provides a handle for further chemistry or influences polarity and reactivity.

Safety and handling considerations apply to nitrile-containing compounds; nitriles can be toxic and require appropriate laboratory precautions.