8-Mercaptoquinoline
{{Chembox
| ImageFile = 8-mercaptoquinoline.png
| ImageSize =
| ImageAlt =
| PIN = Quinoline-8-thiol
| OtherNames = 8-Quinolinethiol
Mercaptoquinoline
Thiooxine
|Section1={{Chembox Identifiers
| CASNo = 491-33-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = F77S9F93J4
| PubChem = 96028
| ChemSpiderID = 86692
| SMILES = c1cc2cccnc2c(c1)S
| InChI = 1/C9H7NS/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H
| InChIKey = MHTSJSRDFXZFHQ-UHFFFAOYAD
| StdInChI = 1S/C9H7NS/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H
| StdInChIKey = MHTSJSRDFXZFHQ-UHFFFAOYSA-N }}
|Section2={{Chembox Properties
| C=9|H=8|N=1|S=1
| Appearance = Colorless crystalline powder
| Density =
| MeltingPtC = 58.5
| BoilingPtC = 296
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
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.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}}
Preparation
Quinoline reacts with chlorosulfuric acid to form quinoline-8-sulfonyl chloride, which reacts with triphenylphosphine in toluene to form 8-mercaptoquinoline.{{cite journal|last1=Rao|first1=Heng|last2=Yu|first2=Wen-Qian|last3=Zheng|first3=Hui-Qin|last4=Bonin|first4=Julien|last5=Fan|first5=Yao-Ting|last6=Hou|first6=Hong-Wei|title=Highly efficient photocatalytic hydrogen evolution from nickel quinolinethiolate complexes under visible light irradiation|journal=Journal of Power Sources|volume=324|year=2016|pages=253–260|issn=0378-7753|doi=10.1016/j.jpowsour.2016.05.095|bibcode=2016JPS...324..253R }}
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