8-Mercaptoquinoline

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]

8-Mercaptoquinoline
Names
Preferred IUPAC name
Quinoline-8-thiol
Other names
8-Quinolinethiol
Mercaptoquinoline
Thiooxine
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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
  • c1cc2cccnc2c(c1)S
Properties
C9H8NS
Molar mass 162.23 g·mol−1
Appearance Colorless solid
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

Preparation

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

References
  1. 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. doi:10.1016/j.ccr.2004.08.024
  2. 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. doi:10.1016/j.jpowsour.2016.05.095. ISSN 0378-7753.
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