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| | Thioxanthen-9-one Basic information |
| | Thioxanthen-9-one Chemical Properties |
| Melting point | 210-213 °C(lit.) | | Boiling point | 371-373 °C715 mm Hg(lit.) | | density | 1.2247 (rough estimate) | | refractive index | 1.5700 (estimate) | | Fp | 371-373°C/715mm | | storage temp. | 2-8°C | | solubility | Chloroform (Slightly), Methanol (Slightly) | | form | neat | | color | Pale Yellow to Light Yellow | | Water Solubility | practically insoluble | | Merck | 14,9369 | | BRN | 140978 | | Stability: | Stable. Incompatible with strong oxidizing agents. | | InChIKey | YRHRIQCWCFGUEQ-UHFFFAOYSA-N | | CAS DataBase Reference | 492-22-8(CAS DataBase Reference) | | NIST Chemistry Reference | Thioxanthone(492-22-8) | | EPA Substance Registry System | Thioxanthone (492-22-8) |
| | Thioxanthen-9-one Usage And Synthesis |
| Description | 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. | | Chemical Properties | slightly yellow crystalline powder | | Uses | Thioxanthen-9-one is a reagent and a starting material for the synthesis of Metixene Hydrochloride. It is also used for highly functional group tolerant and chemoselective oxidation of aromatic or aliphatic sulfides to sulfoxides with hydrogen peroxide. | | Synthesis Reference(s) | Tetrahedron Letters, 35, p. 2195, 1994 DOI: 10.1016/S0040-4039(00)76794-3 | | Purification Methods | It forms yellow needles from CHCl3 or EtOH and sublimes in vacuo. It is soluble in CS2, hot AcOH, and dissolves in conc H2SO4 to give a yellow colour with green fluorescence in VIS light. The sulfone has m 187o (from EtOH), and the hydrazone has m 115o (yellow leaflets from EtOH/*C6H6). The oxime has m 194-196o (from pet ether). [Szmant et al. J Org Chem 18 745 1953, Ullmann et al. Chem Ber 49 2509 1916, NMR: Sharpless et al. Org Magn Res 6 115 1974, Beilstein 17 H 357, 17 I 191, 17 III/IV 5302, 17/10 V 437.] |
| | Thioxanthen-9-one Preparation Products And Raw materials |
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