:Thioxanthone
{{Chembox
| ImageFile = 9H-thioxanthen-9-one 200.svg
| ImageSize = 200px
| ImageAlt =
| PIN = 9H-Thioxanthen-9-one
| OtherNames = Thioxanthenone; 9-Oxothioxanthene; Thioxanthen-9-one
| Section1 = {{Chembox Identifiers
| CASNo = 492-22-8
| CASNo_Ref = {{cascite|correct|CAS}}
| ChEMBL = 83371
| ChemSpiderID = 9873
| EC_number = 207-749-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = EOK1SAC304
| PubChem = 10295
| SMILES = c1ccc2c(c1)c(=O)c3ccccc3s2
| StdInChI =1S/C13H8OS/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H COPY
| StdInChIKey = YRHRIQCWCFGUEQ-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C=13|H=8|O=1|S=1
| Appearance = Pale yellow solid[http://www.sigmaaldrich.com/catalog/product/fluka/89110 Thioxanthone] at Sigma-Aldrich
| Density =
| MeltingPtC = 211
| BoilingPtC = 273
| BoilingPt_notes = (940 hPa)
| Solubility = Nearly insoluble
| SolubleOther = SolubleMerck Index, 14th Edition, 1610
| Solvent = sulfuric acid
| MagSus = −130·10−6 cm3/mol
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
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Thioxanthone is a heterocyclic compound that is a sulfur analog of xanthone.
Thioxanthone can be prepared by the reaction of diphenyl sulfide with phosgene in the presence of catalytic aluminium chloride. This synthesis can be seen as a special case of the Friedel-Crafts acylation. The reduction product is thioxanthene.
Thioxanthone dissolves in concentrated sulfuric acid to give a yellow colored liquid with intense green fluorescence. A mixture of the thioxanthone derivatives of 2- and 4-isopropylthioxanthone (ITX) is used in the printing industry. Pharmaceutical drugs that are derivatives of thioxanthone include hycanthone and lucanthone.
References
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