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8-Mercaptoquinoline


Column 1Column 2
Preferred IUPAC name
Quinoline-8-thiol
Other names
8-QuinolinethiolMercaptoquinolineThiooxine
CAS Number.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}491-33-8
3D model (JSmol)Interactive image
ChemSpider86692
PubChem CID96028
UNIIF77S9F93J4 Y
CompTox Dashboard (EPA)DTXSID70197678
InChI
InChI=1S/C9H7NS/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11HKey: MHTSJSRDFXZFHQ-UHFFFAOYSA-NInChI=1/C9H7NS/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11HKey: MHTSJSRDFXZFHQ-UHFFFAOYAD
SMILES
c1cc2cccnc2c(c1)S
Chemical formulaC9H8NS
Molar mass162.23 g·mol−1
Appearancered dihydrate, blue liquid anhydrous
Melting point58.5 °C (137.3 °F; 331.6 K)
Boiling point296 °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. 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.

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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