Thianthrene

Thianthrene is a sulfur-containing heterocyclic chemical compound. It is a derivative of the parent heterocycle called dithiin. It is notable for its ease of oxidation.

Thianthrene

Names
Preferred IUPAC name Thianthrene[1]
Other names Thianthren; 9,10-Dithiaanthracene; Di-o-phenylene disulfide
Identifiers
CAS Number	92-85-3 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL488176 Y
ChemSpider	6842 Y
ECHA InfoCard	100.001.998
EC Number	202-197-0
PubChem CID	7109
UNII	4139V9M46H Y
CompTox Dashboard (EPA)	DTXSID6059071
InChI InChI=1S/C12H8S2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8H Y Key: GVIJJXMXTUZIOD-UHFFFAOYSA-N Y
SMILES S1c3c(Sc2c1cccc2)cccc3
Properties[2]
Chemical formula	C12H8S2
Molar mass	216.32 g·mol−1
Melting point	151 to 155 °C (304 to 311 °F; 424 to 428 K)
Boiling point	364 to 366 °C (687 to 691 °F; 637 to 639 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Structure and synthesis

Like other 1,4-dithiins but unlike its oxygen analog dibenzodioxin, the shape of thianthrene is not planar. It is bent, with a fold angle of 128° between the two benzo groups.^[3][4][5]

Thianthrene can be prepared by treating benzene with disulfur dichloride in the presence of aluminium chloride.^[6]

History

Thianthrene was first synthesized by John Stenhouse by dry distillation of sodium benzenesulfonate.^[7] Thianthrene is oxidized by sulfuric acid forming a red radical cation.^[8] Thianthrene^•+ has been characterized by Electron paramagnetic resonance. Four different publications describe the crystal structure of salts of thianthrene^•+.^[9]