3-Mercaptopropionitrile is the

organosulfur compound Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature abounds with organosulfur compounds—sulfu ...

with the formula HSCH₂CH₂CN. Containing both thiol and

nitrile In organic chemistry, a nitrile is any organic compound that has a functional group. The prefix ''cyano-'' is used interchangeably with the term ''nitrile'' in industrial literature. Nitriles are found in many useful compounds, including met ...

functional groups, it is a

bifunctional compound In organic chemistry, when a single organic molecule has two different functional groups, it is called a bifunctional molecule . A bifunctional molecule has the properties of two different types of functional groups, such as an alcohol (), amide ( ...

. A colorless liquid, the compound has found some use as a masked form of thiolate.

Preparation and reactions

it is typically prepared from

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 ...

via initial reaction with thiourea. The resulting isothiouronium salt hydrolyzes to the thiol. A A variation on this preparation involves isolation of the disulfide (SCH₂CH₂CN)₂. Zinc reduction of this disulfide gives the thiol. Thioethers derived from S-alkylation of 3-mercaptopropionitrile react with strong bases to give thiolate and acrylonitrile: :RSCH₂CH₂CN + KOBu-t → RSK + CH₂=CHCN + HOBu-t The conversion illustrates the retro-

Michael reaction 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 thiolate is then hydrolyzed :RSK + H⁺ → RSH + K⁺

References

{{DEFAULTSORT:Mercaptopropionitrile, 3- Nitriles Thiols