492-22-8

Basic information

• Product Name: Thioxanthen-9-one
• Synonyms: 9H-Thioxanthene, 9-oxo-;Thiaxanthenone;Thiaxanthon;Thiaxanthone;Thioxanthene, 9-oxo-;Thioxanthene-9-one;Thioxanthenone;THIOXANTHEN-9-ONE
• CAS NO: 492-22-8
• Molecular Formula: C₁₃H₈OS
• Molecular Weight: 212.27
• EINECS: 207-749-4
• Product Categories: Sulphur Derivatives;Heterocyclic Compounds;Naphthyridine,Quinoline;Bioactive Small Molecules;Building Blocks;Cell Biology;Chemical Synthesis;Heterocyclic Building Blocks;Others;S-Containing;T
• Mol File: 492-22-8.mol
• Article Data: 93

Chemical Properties

• Melting Point: 210-213 °C(lit.)
• Boiling Point: 371-373 °C715 mm Hg(lit.)
• Flash Point: 371-373°C/715mm
• Appearance: slightly yellow crystalline powder
• Density: 1.2247 (rough estimate)
• Vapor Pressure: 8E-06mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility: practically insoluble
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,9369
• BRN: 140978
• CAS DataBase Reference: Thioxanthen-9-one(CAS DataBase Reference)
• NIST Chemistry Reference: Thioxanthen-9-one(492-22-8)
• EPA Substance Registry System: Thioxanthen-9-one(492-22-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 492-22-8(Hazardous Substances Data)

Usage

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.

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.]

InChI:InChI=1/C13H8OS/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H

Upstream product

• 493-57-2 benzo-[b]thiophene-2,3-dione 
• 15719-64-9 methylammonium carbonate 
• 261-31-4 thioxanthene 
• 6783-74-0 9H-thioxanthen-9-ol 
• 21083-38-5 dibenzo[b,f][1,5]dithiocin-6,12-dione 
• 139-66-2 diphenyl sulfide 
• 1527-12-4 2-(phenylthio)benzoic acid 
• 15570-18-0 phenyl o-mercaptobenzoate 
• 119-80-2 2,2'-dithiobenzoic acid 
• 55819-78-8 2-acetylmercaptobenzoic acid 
• 13165-80-5 o-(hydroxysulfinyl)benzoic acid 
• 854660-93-8 9-xanthen-9-yl-thioxanthen-9-ol 
• 71-43-2 benzene 
• 108-24-7 acetic anhydride 

Downstream Products

• 90133-50-9 9-mesitylthioxanthen-9-ol 
• 90133-51-0 9-durylthioxanthen-9-ol 
• 76773-25-6 C₃₀H₂₄OS 
• 19019-10-4 9,9-dimethyl-9H-thioxanthene 
• 126593-68-8 9-(2-{5-[Methyl-(3-phenyl-propyl)-amino]-pent-3-ynyl}-[1,3]dithian-2-yl)-9H-thioxanthen-9-ol 
• 126593-20-2 9-(2-{5-[Methyl-(4-phenyl-butyl)-amino]-pent-3-ynyl}-[1,3]dithian-2-yl)-9H-thioxanthen-9-ol 
• 87031-49-0 2,6-Diphenyl-4-thioxanthen-9-ylidenevinylidene-4H-pyran 
• 73453-37-9 Δ^4,9'-2,6-Diphenyl-4-(9'-thioxanthenyl)-4H-thiopyran 
• 118751-80-7 9-(4-Dimethylamino-phenylethynyl)-9H-thioxanthen-9-ol 
• 6630-80-4 9-phenyl-9H-thioxanthen-9-ol 
• 7025-95-8 N,N'-dimethyl-N,N'-diphenylethylenediamine 
• 100-61-8 N-methylaniline 
• 7605-15-4 thioxanthen-9-one 10-oxide 
• 40102-86-1 2,7-dibromo-9H-thioxanthene-9-one 

Relevant articles and documents

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Cu2O-CuO/Chitosan Composites as Heterogeneous Catalysts for Benzylic C?H Oxidation at Room Temperature

Recently, in catalysis, chitosan has been exploited as a macrochelating ligand for metal active species due to the presence of various functional groups in its structure. Moreover, copper-based catalysts are classified as one of the most environmentally friendly catalytic systems and their use for the oxidation of alkylarene has not been established much. Therefore, in this work, the hydrothermal synthesis of copper oxide-chitosan composites as heterogeneous catalysts for the benzylic C?H oxidation of alkylarene was investigated. Characterization results reveal mixed phases of CuO and Cu2O, inferring the ability of chitosan to act as a reducing sugar under the hydrothermal condition. The pre-existing interaction between copper species and chitosan as well as the co-existence of the Cu2O and CuO structures give rise to the efficient performance of the catalysts. The synthesized composites exhibit high activity for the oxidation of fluorene to 9-fluorenone at room temperature and small catalyst loading (1 mol % of Cu, >90 % conversion and 100 % selectivity). Superior TOF was observed, and a good scope of substrates can be converted to corresponding ketones in 48–97 % yields with these copper oxide-chitosan catalysts. In addition, the catalysts can be used for up to nine cycles without significant decrease of the activity.

HCl-Catalyzed Aerobic Oxidation of Alkylarenes to Carbonyls

The construction of C?O bonds through C?H bond functionalization remains fundamentally challenging. Here, a practical chlorine radical-mediated aerobic oxidation of alkylarenes to carbonyls was developed. This protocol employed commercially available HCl as a hydrogen atom transfer (HAT) reagent and air as a sustainable oxidant. In addition, this process exhibited excellent functional group tolerance and a broad substrate scope without the requirement for external metal and oxidants. The mechanistic hypothesis was supported by radical trapping, 18O labeling, and control experiments.