Thioxanthone

Thioxanthone
Names
Preferred IUPAC name
9H-Thioxanthen-9-one
Other names
Thioxanthenone; 9-Oxothioxanthene; Thioxanthen-9-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.046
EC Number
  • 207-749-4
UNII
  • 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
  • c1ccc2c(c1)c(=O)c3ccccc3s2
Properties
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)
Nearly insoluble
Solubility in sulfuric acid Soluble[2]
−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 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.[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.

References

  1. ^ Thioxanthone at Sigma-Aldrich
  2. ^ a b c d Merck Index, 14th Edition, 1610
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