Thianthrene

Thianthrene
Names
	IUPAC name Thianthrene
	Other names Thianthren; 9,10-Dithiaanthracene; Di-o-phenylene disulfide
Identifiers
CAS Number	92-85-3 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL488176 ;
ChemSpider	6842 ;
ECHA InfoCard	100.001.998
EC Number	202-197-0;
PubChem CID	7109;
UNII	4139V9M46H ;
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 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

Thianthrene at Sigma-Aldrich
Hosoya, S. (1963). "Molecular shapes of thianthrene and related heterocyclic compounds". Acta Crystallographica. 16 (4): 310–312. doi:10.1107/S0365110X63000797.
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.
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.
US patent 3997560, "Process for the manufacture of thianthrene", issued 1976-12-14.
Stenhouse, J. (1869). "Ueber die Producte der trockenen Destillation der sulfobenzolsauren Salze" [On the Dry Distillation Products from Sulfobenzoic Acid Salts] (PDF). Annalen der Chemie und Pharmacie (in German). 149 (2): 247–255. doi:10.1002/jlac.18691490216.
W. Dilthey: Versammlungsberichte Bonner Chemische Gesellschaft, Angewandte Chemie, Volume 42, Issue 24, pp. 668–670, 15. June 1929; doi:10.1002/ange.19290422405.
Shine, Henry J. (July 1998). "EPR and the History of the Thianthrene Cation Radical". Foundations of modern EPR. ISBN 978-981-02-3295-5.

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[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" [On the Dry Distillation Products from Sulfobenzoic Acid Salts] (PDF). Annalen der Chemie und Pharmacie (in German). 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.