Cyanoethylation is a process for the attachment of CH₂CH₂CN group to another organic substrate. The method is used in the synthesis of organic compounds. Cyanoethylation entails addition of protic nucleophiles to

acrylonitrile Acrylonitrile is an organic compound with the formula and the structure . It is a colorless, volatile liquid although commercial samples can be yellow due to impurities. It has a pungent odor of garlic or onions. In terms of its molecular ...

. Typical protic nucleophiles are

alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...

thiol In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl gro ...

s, and

amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituen ...

s. Two new bonds form: C-H and C-X (X = carbon, nitrogen, sulfur, phosphorus, etc): :

\mathrm

The β-carbon atom that is furthest from the nitrile group is positively polarized and therefore binds the heteroatom on the nucleophile. Acrylonitrile is a

Michael acceptor In organic chemistry, the Michael reaction or Michael addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce a Michael adduct by creating a carbon ...

. The reaction is normally

catalyzed Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...

by a base. 144px, Tris(cyanoethyl)phosphine is produced by the cyanoethylation of phosphine. Cyanethylation is used to prepared numerous commercial chemicals. Detailed laboratory procedures are available for several variants of this reaction. *Cyanoethylation of amines. *Cyanoethylation of phosphines. *Cyanoethylation of carbon nucleophiles. In one commercial example, acetone is cyanoethylated to give the keto hexanenitrile, a precursor to

2-methylpyridine 2-Methylpyridine, or 2-picoline, is the compound described with formula C6H7N. 2-Picoline is a colorless liquid that has an unpleasant odor similar to pyridine. It is mainly used to make vinylpyridine and the agrichemical nitrapyrin. Synthesis 2 ...

. An alternative method for cyanoethylation entails alkylation of the substrate with

3-chloropropionitrile 3-Chloropropionitrile is an organic compound with the formula ClCH2CH2CN. A colorless liquid, it is prepared by the reaction of hydrogen chloride with acrylonitrile. It is used commercially as a precursor to the drug famotidine. It is an alkyla ...

De-cyanoethylation

Cyanoethyl is a

protecting group A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis. In many ...

. It is removed by treatment with base: :RNuCH₂CH₂CN + OH⁻ → RNu⁻ + CH₂=CHCN + H₂O This methodology is popular in the synthesis of oligonucleotides.{{cite journal , doi=10.1039/c9ob00501c, title=Chemical ADP-ribosylation: Mono-ADPr-peptides and oligo-ADP-ribose, year=2019, last1=Liu, first1=Qiang, last2=Van Der Marel, first2=Gijsbert A., last3=Filippov, first3=Dmitri V., journal=Organic & Biomolecular Chemistry, volume=17, issue=22, pages=5460–5474, pmid=31112180, s2cid=160014127, doi-access=free

References

Chemical reactions