Thianthrene

Thianthrene

Names
IUPAC name Thianthrene
Other names Thianthren; 9,10-Dithiaanthracene; Di-o-phenylene disulfide
Identifiers
CAS Number	92-85-3
ChEMBL	ChEMBL488176
ChemSpider	6842
EC Number	202-197-0
Jmol interactive 3D	Image
PubChem	7109
InChI InChI=1S/C12H8S2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8H Key: GVIJJXMXTUZIOD-UHFFFAOYSA-N
SMILES S1c3c(Sc2c1cccc2)cccc3
Properties[1]
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).
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Infobox references

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.

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.^[2][3][4]

Thianthrene can be prepared by treating benzene with disulfur dichloride in the presence of aluminium chloride.^[5]

History

Thianthrene was first synthesized by John Stenhouse by dry distillation of sodium benzenesulfonate.^[6] Thianthrene is oxidized by sulfuric acid forming a red radical cation.^[7] Thianthrene^•+ has been characterized by Electron paramagnetic resonance. Four different publications describe the crystal structure of salts of thianthrene^•+.^[8]

References

1. Thianthrene at Sigma-Aldrich
2. Hosoya, S. (1963). "Molecular shapes of thianthrene and related heterocyclic compounds". Acta Crystallographica 16 (4): 310–312. doi:10.1107/S0365110X63000797.
3. Gallaher, K. L.; Bauer, S. H. (1975). "Structure and inversion potential of thianthren". Journal of the Chemical Society, Faraday Transactions 2 71: 1173–1182. doi:10.1039/F29757101173.
4. Aroney, M. J.; Le Fèvre, R. J. W.; Saxby, J. D. (1965). "92. Molecular polarisability. The apparent conformations of thianthren and of three of its oxides as solutes in benzene". Journal of the Chemical Society (Resumed): 571–575. doi:10.1039/JR9650000571.
5. US patent 3997560, "Process for the manufacture of thianthrene", issued 1976-12-14 .
6. Stenhouse, J. (1869). "Ueber die Producte der trockenen Destillation der sulfobenzolsauren Salze". Annalen der Chemie und Pharmacie 149 (2): 247–255. doi:10.1002/jlac.18691490216.
7. W. Dilthey: Versammlungsberichte Bonner Chemische Gesellschaft, Angewandte Chemie, Volume 42, Issue 24, pp. 668–670, 15. June 1929; doi:10.1002/ange.19290422405.
8. Shine, Henry J. (July 1998). "EPR and the History of the Thianthrene Cation Radical". Foundations of modern EPR. ISBN 978-981-02-3295-5.