8-Mercaptoquinoline

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8-Mercaptoquinoline
8-mercaptoquinoline.png
Names
Preferred IUPAC name
Quinoline-8-thiol
Other names
8-Quinolinethiol
Mercaptoquinoline
Thiooxine
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
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
Appearancered dihydrate, blue liquid anhydrous
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).

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. [1] [2]

8-Mercaptoquinoline functions as a bidentate ligand for many metal ions. [3]

Preparation

8-Mercaptoquinoline is usually prepared via quinoline-8-sulfonyl chloride. This species can be reduced with stannous chloride. [2] Triphenylphosphine has also been used as a reductant. [4]

8-quinolinesulfonyl chloride to 8-mercaptoquinoline.png

References

  1. ↑ Lee, H. S. (1963). "Novel Synthesis of 8-Mercaptoquinoline". Canadian Journal of Chemistry. 41 (6): 1646–1647. Bibcode:1963CaJCh..41.1646L. doi:10.1139/v63-234.
  2. 1 2 Corsini, Alfio.; Fernando, Quintus.; Freiser, Henry. (1963). "8-Mercaptoquinoline as an Analytical Reagent. Dissociation and Metal Chelate Formation Constants". Analytical Chemistry. 35 (10): 1424–1428. doi:10.1021/ac60203a058.
  3. ↑ 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
  4. ↑ 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.
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