3-Mercaptopropionitrile
chemical compound
3-Mercaptopropionitrile is the organosulfur compound with the formula HSCH2CH2CN. 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.
Preparation and reactions
it is typically prepared from 3-chloropropionitrile via initial reaction with thiourea. The resulting isothiouronium salt hydrolyzes to the thiol. 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.
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