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

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

Uses

Used in Pharmaceutical Industry:
Thioxanthone is utilized as a reagent and a starting material for the synthesis of Metixene Hydrochloride, a pharmaceutical drug. It serves as a crucial component in the development of various pharmaceutical compounds.
Used in Chemical Synthesis:
Thioxanthone is employed for highly functional group tolerant and chemoselective oxidation of aromatic or aliphatic sulfides to sulfoxides, using hydrogen peroxide as the oxidizing agent. This application highlights its versatility in chemical reactions and its importance in the synthesis of various organic compounds.
Used in Printing Industry:
A mixture of thioxanthone derivatives, specifically 2and 4-isopropylthioxanthone (ITX), is used in the printing industry. These derivatives contribute to the production of high-quality prints by enhancing the properties of inks and other printing materials.

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

• 6783-74-0 9H-thioxanthen-9-ol 
• 7605-15-4 thioxanthen-9-one 10-oxide 
• 129846-96-4 (2-(2-fluorophenylthio)phenyl)acetonitrile 
• 59181-71-4 9-Cyano-10-methyl-10-thiaanthracene 
• 83986-03-2 5-Chloro-2-(2-fluorophenylthio)-α-(1-methyl-4-piperidyl)benzyl alcohol 
• 161-87-5 dispiro[thioxanthene-9,2'-thiirane-3',9''-xanthene] 
• 161-88-6 dispiro[thioxanthene-9,2'-thiirane-3',9''-thioxanthene] 
• 257-15-8 dibenzo[b,f]-1,4-thiazepine 
• 7664-93-9 sulfuric acid 
• 13165-80-5 o-(hydroxysulfinyl)benzoic acid 
• 71-43-2 benzene 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 864512-14-1 2-iodophenyl 4-chlorobenzenesulfonate 
• 147-93-3 Thiosalicylic acid 

Downstream Products

• 27090-16-0 9,9'-bi(9H-thioxanthen-9-ylidene) 
• 858840-55-8 9,9-bis-benzylmercapto-thioxanthene 
• 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 

Relevant articles and documents

Photosensitized Desulfurization of Heterocyclic Thioketones and Its Accompanied Chemiluminescence

Photosensitized oxygenation of 10-methyl-9(10H)-acridinethione, 9H-xanthene-9-thione, and 9H-thioxanthene-9-thione at -78 deg C gave the corresponding ketones, 10-methyl-9(10H)-acridinone, 9H-xanthen-9-one, and 9H-thioxanthen-9-one quantitatively in a 3-10 min-irradiation.Weak chemiluminescence was observed from the irradiated solution upon warming-up.

Poly(ethylene glycol) dimethyl ether mediated oxidative scission of aromatic olefins to carbonyl compounds by molecular oxygen

A simple, and practical oxidative scission of aromatic olefins to carbonyl compounds using O2as the sole oxidant with poly(ethylene glycol) dimethyl ether as a benign solvent has been developed. A wide range of monosubstituted,gem-disubstituted, 1,2-disubstituted, trisubstituted and tetrasubstituted aromatic olefins was successfully converted into the corresponding aldehydes and ketones in excellent yields even with gram-scale reaction. Some control experiments were also conducted to support a possible reaction pathway.

Method for preparing aldehyde ketone compound through olefin oxidation

The invention provides a method for preparing an aldehyde ketone compound by olefin oxidation, which relates to an olefin oxidative cracking reaction in which oxygen participates. The method comprises the following specific steps: in the presence of a solvent and an oxidant, carrying out oxidative cracking on an olefin raw material to obtain a corresponding aldehyde ketone product. Compared with the traditional method, the method does not need to add any catalyst or ligand, does not need to use high-pressure oxygen, has the advantages of simple and mild reaction conditions, environment friendliness, low cost, high atom economy and the like, is wide in substrate application range and high in yield, and has a wide application prospect in the aspects of synthesis of aldehyde ketone medical intermediates and chemical raw materials.

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF

The present invention provides a novel compound that can improve the luminous efficiency, stability and life span of the element, an organic electronic element using the same, and an electronic device thereof.

Scalable electrochemical reduction of sulfoxides to sulfides

A scalable reduction of sulfoxides to sulfides in a sustainable way remains an unmet challenge. This report discloses an electrochemical reduction of sulfoxides on a large scale (>10 g) under mild reaction conditions. Sulfoxides are activated using a substoichiometric amount of the Lewis acid AlCl3, which could be regeneratedviaa combination of inexpensive aluminum anode with chloride anion. This deoxygenation process features a broad substrate scope, including acid-labile substrates and drug molecules.

Synthesis of xanthones, thioxanthones and Acridones by a metal-free photocatalytic oxidation using visible light and molecular oxygen

9H-Xanthenes, 9H-thioxanthenes and 9,10-dihydroacridines can be easily oxidized to the corresponding xanthones, thioxanthones and acridones, respectively, by a simple photo-oxidation procedure carried out using molecular oxygen as oxidant under the irradiation of visible blue light and in the presence of riboflavin tetraacetate as a metal-free photocatalyst. The obtained yields are high or quantitative.

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.

Ultraviolet-light-induced aerobic oxidation of benzylic C(sp3)-H of alkylarenes under catalyst- and additive-free conditions

A mild and efficient system has been discovered for the synthesis of α-aryl carbonyl compounds via oxidation of benzylic C–H to C[dbnd]O bonds. This ultraviolet-light-mediated oxygenation reaction exhibited excellent substrate scope including various xanthenes, thioxanthenes and 9, 10-dihydroacridines and afforded the corresponding ketones with good to excellent yields under catalyst- and additive-free conditions at room temperature.

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.

Formation and Disproportionation of Xanthenols to Xanthenes and Xanthones and Their Use in Synthesis

A facile and versatile strategy employing TiCl4-mediated cyclization followed by a Cannizzaro reaction has been developed for the synthesis of various xanthene derivatives. The reaction proceeded smoothly to afford both xanthenes/xanthones or their sulfur derivatives and tolerated a wide range of electronically diverse substrates. Using this methodology, pranoprofen was synthesized in three steps in 59% overall yield from commercially available starting materials.