thianthrene
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477863238
| ImageFile = Thianthrene.svg
| ImageFile2 = Thianthrene.png
| PIN = Thianthrene{{cite book |author=International Union of Pure and Applied Chemistry |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=The Royal Society of Chemistry |pages=216 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}
| OtherNames = Thianthren; 9,10-Dithiaanthracene; Di-o-phenylene disulfide
|Section1={{Chembox Identifiers
| CASNo = 92-85-3
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4139V9M46H
| EINECS = 202-197-0
| PubChem = 7109
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 488176
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6842
| SMILES = S1c3c(Sc2c1cccc2)cccc3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI=1S/C12H8S2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GVIJJXMXTUZIOD-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| Properties_ref = [http://www.sigmaaldrich.com/catalog/product/aldrich/122440?lang=en®ion=US Thianthrene] at Sigma-Aldrich
| C=12 | H=8 | S=2
| Appearance =
| Density =
| MeltingPtC = 151 to 155
| BoilingPtC = 364 to 366
| Solubility =
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|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
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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.{{Cite journal | last1 = Hosoya | first1 = S. | title = Molecular shapes of thianthrene and related heterocyclic compounds | journal = Acta Crystallographica | volume = 16 | pages = 310–312 | year = 1963 | doi = 10.1107/S0365110X63000797 | issue = 4| doi-access = free | bibcode = 1963AcCry..16..310H }}{{cite journal | last1 = Gallaher | first1 = K. L. | last2 = Bauer | first2 = S. H. | title = Structure and inversion potential of thianthren | journal = Journal of the Chemical Society, Faraday Transactions 2 | volume = 71 | pages = 1173–1182 | year = 1975 | doi = 10.1039/F29757101173}}{{cite journal | last1 = Aroney | first1 = M. J. | last2 = Le Fèvre | first2 = R. J. W. | last3 = Saxby | first3 = J. D. | title = 92. Molecular polarisability. The apparent conformations of thianthren and of three of its oxides as solutes in benzene | journal = Journal of the Chemical Society (Resumed) | pages = 571–575 | year = 1965 | doi = 10.1039/JR9650000571}}
Thianthrene can be prepared by treating benzene with disulfur dichloride in the presence of aluminium chloride.{{cite patent | title = Process for the manufacture of thianthrene | country = US | number = 3997560 | status = patent | gdate = 1976-12-14}}.
History
Thianthrene was first synthesized by John Stenhouse by dry distillation of sodium benzenesulfonate.{{cite journal|last1=Stenhouse|first1= J.|trans-title=On the Dry Distillation Products from Sulfobenzoic Acid Salts|language=German|title= Ueber die Producte der trockenen Destillation der sulfobenzolsauren Salze| journal = Annalen der Chemie und Pharmacie| volume = 149| pages = 247–255| year = 1869| doi = 10.1002/jlac.18691490216| issue = 2| url = https://zenodo.org/record/1427287}} Thianthrene is oxidized by sulfuric acid forming a red radical cation.W. Dilthey: Versammlungsberichte Bonner Chemische Gesellschaft, Angewandte Chemie, Volume 42, Issue 24, pp. 668–670, 15. June 1929; {{doi|10.1002/ange.19290422405}}. Thianthrene•+ has been characterized by Electron paramagnetic resonance. Four different publications describe the crystal structure of salts of thianthrene•+.{{cite book | chapter-url = https://books.google.com/books?id=1LdKSYIQtPYC&pg=PA202 | chapter = EPR and the History of the Thianthrene Cation Radical | first = Henry J. | last = Shine | title = Foundations of modern EPR | isbn = 978-981-02-3295-5 | date = July 1998| publisher = World Scientific }}