CAS 492-22-8 Thioxanthone (HCID 10295)

Overview

structure in first source

Names & identifiers

Preferred name: Thioxanthone
IUPAC: thioxanthen-9-one
English name: Thioxanthen-9-one
Molecular formula: C13H8OS
Molecular weight: 212.27

Names & synonyms

Thioxanthen-9-one492-22-89H-THIOXANTHEN-9-ONEThioxanthone9-ThioxanthoneThiaxanthenoneThioxanthenoneThiaxanthon9H-Thioxanthene, 9-oxo-EOK1SAC304NSC-15912NSC-658181

Show more names

9-THIOXANTHENONE9-thione1-xanthenone

DTXSID8060082RefChem:189678DTXCID0040674207-749-4ThiaxanthoneThioxanthene-9-one9-Oxothioxanthene10-Thioxanthone

Database identifiers

CAS: 492-22-8
PubChem CID: 10295
DTXSID: DTXSID8060082
ChEMBL: CHEMBL83371
UNII: EOK1SAC304
EC Number: 207-749-4
Nikkaji: J1.555E

Properties

Computed structural properties

XLogP: 4
Topological polar surface area: 42.4 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 0
Heavy atoms: 15
Formal charge: 0
Complexity: 239

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Other Aromatic Compounds

SpringerMaterials PropertiesSchoenflies notation

Vapor Pressure0.0000135 [mmHg]

Physical DescriptionYellow solid; [Merck Index] Light yellow crystalline solid; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point: 210 · 210-213 °C(lit.)
Boiling point: 371 · 371-373 °C715 mm Hg(lit.)
Density: 1.2247 · 1.2247 (rough estimate)
refractive index: 1.57 · 1.5700 (estimate)
Flash point: 371 · 371-373°C/715mm
storage temp.: 2 · 2-8°C
solubility: Chloroform (Slightly), Methanol (Slightly)
form: Solid
color: Pale Yellow to Light Yellow
Water Solubility: practically insoluble
Merck: 14 · 14,9369
BRN: 140978 · 140978
Stability: Stable. Incompatible with strong oxidizing agents.
InChI: 1S/C13H8OS/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H
InChIKey: YRHRIQCWCFGUEQ-UHFFFAOYSA-N
SMILES: O=C1c2ccccc2Sc3ccccc13
CAS DataBase Reference: 492 · 492-22-8(CAS DataBase Reference)
FDA UNII: 1 SAC304 · EOK1SAC304
NIST Chemistry Reference: Thioxanthone(492-22-8)
EPA Substance Registry System: Thioxanthone (492-22-8)
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 22 · 22-24/25-37/39-26
WGK Germany: 3 · 3
Hazard Note: Irritant
TSCA: TSCA listed
HS Code: 29349990 · 29349990
Storage Class: 13 · 13 - Non Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 97.4% (37 of 38) of all reports.

Not Classified

Aggregated GHS information provided per 38 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS]

Hazard Classes and CategoriesNot Classified

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
tsca: TSCA listed
hs_code: 29349990
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
hazard_note: Irritant
safety_code: 22-24/25-37/39-26
Storage Class: 13 - Non Combustible Solids
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Uses & manufacturing

General Manufacturing Information9H-Thioxanthen-9-one: ACTIVE

Applications · 2 items

DescriptionThioxanthone 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.

UsesThioxanthen-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.