3-Mercaptopropionitrile

[1] Containing both thiol and nitrile functional groups, it is a bifunctional compound.

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

The resulting isothiouronium salt hydrolyzes to the thiol.

[2] A variation on this preparation involves isolation of the disulfide (SCH2CH2CN)2.

[3] Thioethers derived from S-alkylation of 3-mercaptopropionitrile react with strong bases to give thiolate and acrylonitrile: The conversion illustrates the retro-Michael reaction.