Thioxanthen-9-one

ChemicalBook > CAS DataBase List > Thioxanthen-9-one

Thioxanthen-9-one

Product Name: Thioxanthen-9-one
CAS No.: 492-22-8
Chemical Name: Thioxanthen-9-one
Synonyms: THIOXANTHONE;9H-THIOXANTHEN-9-ONE;Thioxanthenone;Thioxanthene-9-one;Thiaxanthon;Thiaxanthone;1-xanthenone;Thiaxanthenone;9-THIOXANTHONE;9-THIOXANTHENONE
CBNumber: CB5228030
Molecular Formula: C13H8OS
Formula Weight: 212.27
MOL File: 492-22-8.mol

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Thioxanthen-9-one Property

Melting point:: 210-213 °C(lit.)
Boiling point:: 371-373 °C715 mm Hg(lit.)
Density: 1.2247 (rough estimate)
refractive index: 1.5700 (estimate)
Flash point:: 371-373°C/715mm
storage temp.: 2-8°C
solubility: Chloroform (Slightly), Methanol (Slightly)
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)

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 22-24/25-37/39-26
WGK Germany: 3
Hazard Note: Irritant
TSCA: Yes
HS Code: 29349990

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: T1305000
Product name: Thioxanthone
Purity: European Pharmacopoeia (EP) Reference Standard
Packaging: t1305000
Price: $223
Updated: 2024/03/01

Sigma-Aldrich

Product number: T34002
Product name: Thioxanthen-9-one
Purity: 97%
Packaging: 25g
Price: $66.9
Updated: 2022/05/15

TCI Chemical

Product number: T2351
Product name: Thioxanthone
Purity: >98.0%(GC)
Packaging: 25g
Price: $353
Updated: 2024/03/01

TRC

Product number: T384500
Product name: Thioxanthen-9-one
Packaging: 250mg
Price: $85
Updated: 2021/12/16

Chem-Impex

Product number: 43231
Product name: Thioxanthone,≥98%(GC)
Purity: ≥98%(GC)
Packaging: 25G
Price: $115.55
Updated: 2021/12/16

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Thioxanthen-9-one Chemical Properties,Usage,Production

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

Reactivity Profile

Thioxanthen-9-one can mediate reactions via triplet energy transfer (EnT), hydrogen atom transfer (HAT) or single electron transfer (SET). Apart from the use in polymerisation chemistry, thioxanthone and its derivatives have been employed in a wide variety of chemical transformations, such as photoisomerisation reactions, photoinduced rearrangements, [2 + 2] photocycloadditions, Paterno–Buchi cycloadditions, photoredox catalysis and cross-coupling reactions leading to C–O, C–N, C–P and other bond formation[1].

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.]

Structure and conformation

Thioxanthen-9-one (TX) is a aromatic ketone. In comparison with other aromatic ketones, TX has a high triplet energy and a relatively long triplet lifetime, while it has the ability to participate successfully in merger reactions with metal complexes. The conformation of TX is not fixed, but it interconverts from a planar (C2v) to a non-planar conformation. In the case of TX, the intersystem crossing of an electron normally occurs from a non-bonding orbital (n) to an anti-bonding pi orbital (π*) (nπ* configuration) and occurs 103 times faster than in the case of migration from the same type of molecular orbital (ππ* migration).Theoretical studies support that TX's low lying triplet state is close enough to the singlet state, favoring in this way internal conversion (IC) and ISC upon photoexcitation. Due to its high triplet energy, TX is an efficient sensitizer for oxygen, leading to singlet oxygen, since the excitation of oxygen requires around 23 kcal mol^-¹[1].

References

[1] Nikitas N, et al. Thioxanthone: a powerful photocatalyst for organic reactions. Organic & Biomolecular Chemistry, 2021; 19: 5237-5253.

Thioxanthen-9-one Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Thioxanthen-9-one manufacturers

Wuhan Cell Pharmaceutical Co., Ltd

Product: Thioxanthen-9-one 492-22-8
Price: US $2.00-385.00/g
Min. Order: 1g
Purity: 99%
Supply Ability: 100kg
Release date: 2023-03-30

qingdao future trading Co., Ltd

Product: Thioxanthen-9-one 492-22-8
Price: US $650.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 10tons
Release date: 2023-06-14

Anhui Zhongda Biotechnology Co., Ltd

Product: Thiaxanthone 492-22-8
Price: US $90.00-70.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 10000/month
Release date: 2023-08-18

492-22-8, Thioxanthen-9-oneRelated Search:

Chlortalidone EQUILIN PIPERACILLIN Hexythiazox Buprofezin 2-Thiophenecarboxylic acid hydrazide 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole Ethyl thiazole-2-carboxylate Thiazolo[5,4-c]pyridine 2,4-Dihydroxythieno[2,3-d]pyrimidine 2-Thiopheneboronic acid Thiazole Thieno[3,2-b]thiophene 9-Fluorenone Benziothiazolinone 2-Isopropyl-9H-thioxanthen-9-one,9H-Thioxanthen-9-one, 2-(1-methylethyl)- 2-Trifluoromethyl-10-Thioxanthenone,2-(Trifluoromethyl)thioxanthen-9-one 98%,2-(Trifluoromethyl)thioxanthen-9-one99% 1-chloro-9H-thioxanthen-9-one

9H-Thioxanthene, 9-oxo-

Thiaxanthenone

Thiaxanthon

Thiaxanthone

Thioxanthene, 9-oxo-

Thioxanthene-9-one

Thioxanthenone

THIOXANTHEN-9-ONE

THIOXANTHONE

9-OXOTHIOXANTHENE

9-THIOXANTHENONE

9-THIOXANTHONE

9H-THIOXANTHEN-9-ONE

Thioxanthen-9-one,98%

THIOXANTHAN-9-ONE

9H-Thioxanthen-9-one 98%

9-Oxo-9H-thioxanthene

Thioxanthen-9-one, >=99%

Thioxanthen-9-one 97%

9-Oxothioxanthene, Thioxanthen-9-one

9-Oxothioxanthene, Thioxanthone

1-xanthenone

Thioxanthone CRS

9H-Thioxanthen-9-one (Thioxanthone)

Metixene EP Impurity B

Metixene Impurity 2 (Metixene EP Impurity B)

methixene Impurity 1

Compound PDK0236

Metixene Hydrochloride Impurity B

Metixene Hydrochloride EP Impurity B

492-22-8

C13H8OS

Heterocyclic Building Blocks

S-Containing

Others

Building Blocks

Sulphur Derivatives

Heterocyclic Compounds

Naphthyridine,Quinoline

Bioactive Small Molecules

Building Blocks

Cell Biology

Chemical Synthesis

Heterocyclic Building Blocks

Others

S-Containing

492-22-8