Thioxanthone

Thioxanthone is a heterocyclic compound that is a sulfur analog of xanthone.

Thioxanthone

Names
Preferred IUPAC name 9H-Thioxanthen-9-one
Other names Thioxanthenone; 9-Oxothioxanthene; Thioxanthen-9-one
Identifiers
CAS Number	492-22-8 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL83371
ChemSpider	9873
ECHA InfoCard	100.007.046
EC Number	207-749-4
PubChem CID	10295
UNII	EOK1SAC304 Y
CompTox Dashboard (EPA)	DTXSID8060082
InChI InChI=1S/C13H8OS/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H COPY Key: YRHRIQCWCFGUEQ-UHFFFAOYSA-N
SMILES c1ccc2c(c1)c(=O)c3ccccc3s2
Properties
Chemical formula	C13H8OS
Molar mass	212.27 g·mol−1
Appearance	Pale yellow solid[1]
Melting point	211 °C (412 °F; 484 K)[2]
Boiling point	273 °C (523 °F; 546 K)[2] (940 hPa)
Solubility in water	Nearly insoluble
Solubility in sulfuric acid	Soluble[2]
Magnetic susceptibility (χ)	−130·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Thioxanthone can be prepared by the reaction of diphenyl sulfide with phosgene in the presence of catalytic aluminium chloride.^[2] 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.