8-Mercaptoquinoline is the organosulfur compound with the formula C9H7NSH. It is a derivative of the heterocycle quinoline, substituted in the 8-position with a thiol group. The compound is an analog of 8-hydroxyquinoline, a common chelating agent. In terms of physical properties, this compound crystallizes as a red solid dihydrate but the anhydrous compound is a blue liquid.
8-Mercaptoquinoline functions as a bidentate ligand for many metal ions.Fleischer, Holger "Structural chemistry of complexes of (n - 1)d10nsm metal ions with β-N-donor substituted thiolate ligands (m=0, 2)" Coordination Chemistry Reviews 2005, volume 249, pp. 799-827.
Preparation 8-Mercaptoquinoline is usually prepared via quinoline-8-sulfonyl chloride. This species can be reduced with stannous chloride. Triphenylphosphine has also been used as a reductant.
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