8-Mercaptoquinoline

8-Mercaptoquinoline
Names
	Preferred IUPAC name Quinoline-8-thiol
	Other names 8-Quinolinethiol; Mercaptoquinoline; Thiooxine
Identifiers
CAS Number	491-33-8;
3D model (JSmol)	Interactive image;
ChemSpider	86692;
PubChem CID	96028;
UNII	F77S9F93J4 ;
CompTox Dashboard (EPA)	DTXSID70197678 ;
	InChI InChI=1S/C9H7NS/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H Key: MHTSJSRDFXZFHQ-UHFFFAOYSA-N; InChI=1/C9H7NS/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H Key: MHTSJSRDFXZFHQ-UHFFFAOYAD;
	SMILES c1cc2cccnc2c(c1)S;
Properties
Chemical formula	C9H8NS
Molar mass	162.23 g·mol−1
Appearance	Colorless crystalline powder
Melting point	58.5 °C (137.3 °F; 331.6 K)
Boiling point	296 °C (565 °F; 569 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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. The compound is a colorless solid.^[1]

Preparation

Quinoline reacts with chlorosulfuric acid to form quinoline-8-sulfonyl chloride, which reacts with triphenylphosphine in toluene to form 8-mercaptoquinoline.^[2]

^ Fleischer, Holger "Structural chemistry of complexes of (n - 1)d¹⁰ns^m metal ions with β-N-donor substituted thiolate ligands (m=0, 2)" Coordination Chemistry Reviews 2005, volume 249, pp. 799-827. doi:10.1016/j.ccr.2004.08.024
^ Rao, Heng; Yu, Wen-Qian; Zheng, Hui-Qin; Bonin, Julien; Fan, Yao-Ting; Hou, Hong-Wei (2016). "Highly efficient photocatalytic hydrogen evolution from nickel quinolinethiolate complexes under visible light irradiation". Journal of Power Sources. 324: 253–260. Bibcode:2016JPS...324..253R. doi:10.1016/j.jpowsour.2016.05.095. ISSN 0378-7753.