: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

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| 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

| MeltingPt_ref =

| BoilingPtC = 273

| BoilingPt_notes = (940 hPa)

| BoilingPt_ref =

| Solubility = Nearly insoluble

| SolubleOther = SolubleMerck Index, 14th Edition, 1610

| Solvent = sulfuric acid

| MagSus = −130·10−6 cm3/mol

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| 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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