Thioxanthen 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
Sarm 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.
Reactivity Profile Sarm 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.
Structure and conformation
Thio-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.
Thioxanthen-9-one powder 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)
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)
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)
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)
More Introduction:https://pubchem.ncbi.nlm.nih.gov/compound/Thioxanthen-9-one
