| Identification | More | [Name]
Thianthrene | [CAS]
92-85-3 | [Synonyms]
AKOS 90207
DI-O-PHENYLENE DISULFIDE
DIPHENYLENE DISULFIDE
THIANTHRENE
9,10-Dithiaanthracene
dibenzo-1,4-dithiin
Thiaanthrene
Thianthren
THIANTHRENE, 99+%
diphylene disulfide
Dibenzodithiodioxane | [EINECS(EC#)]
202-197-0 | [Molecular Formula]
C12H8S2 | [MDL Number]
MFCD00005065 | [Molecular Weight]
216.32 | [MOL File]
92-85-3.mol |
| Chemical Properties | Back Directory | [Melting point ]
151-155 °C (lit.) | [Boiling point ]
364-366 °C (lit.) | [density ]
1.4420 | [refractive index ]
1.6210 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMF: soluble | [form ]
powder to crystal | [color ]
White to Light yellow | [BRN ]
83046 | [InChI]
1S/C12H8S2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8H | [InChIKey]
GVIJJXMXTUZIOD-UHFFFAOYSA-N | [SMILES]
S1c2ccccc2Sc3ccccc13 | [CAS DataBase Reference]
92-85-3(CAS DataBase Reference) | [NIST Chemistry Reference]
Thianthrene(92-85-3) | [EPA Substance Registry System]
92-85-3(EPA Substance) |
| Hazard Information | Back Directory | [Chemical Properties]
White to off-white solid | [Uses]
Thianthrene has been used to study aqueous solubilities of several solid nitrogen-, sulfur- and oxygen-containing heterocyclic derivatives of anthracene, phenanthrene and fluorene. It has been used in determination of partition coefficients of several sulfur-containing aromatics in 1-hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide and supercritical carbon dioxide. | [Definition]
ChEBI: The organosulfur heterocyclic compound that is the parent compound of the thianthrenes, a tricyclic structure comprising two benzene rings fused to the b and e sides of 1,4-dithin. | [Preparation]
Thianthrene was first synthesized by John Stenhouse by dry distillation of sodium benzenesulfonate. Thianthrene can be prepared by treating benzene with disulfur dichloride in the presence of aluminium chloride. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 31, p. 4071, 1966 DOI: 10.1021/jo01350a045 | [General Description]
Thianthrene undergoes liquid phase tert-butylation in the presence of large pore zeolites and mesoporous aluminosilicates catalyst to yield tert-butyl derivatives. Thianthrene on oxidation in the presence of hydrogen peroxide and ligninase as catalyst from Phanerochaete chrysosporium yields thianthrene monosulfoxide. | [storage]
Store at -20°C | [Purification Methods]
thianthrene from Me2CO (charcoal), AcOH or EtOH. It sublimes in a vacuum. [Beilstein 19 H 45, 19 I 619, 19 II 34, 19 III/IV 347, 19/2 V 49.] | [References]
[1] STENHOUSE J. Ueber die Producte der trockenen Destillation der sulfobenzolsauren Salze[J]. European Journal of Organic Chemistry, 1869, 149 2: 247-255. DOI:10.1002/jlac.18691490216.
[2] BOGDAN BODUSZEK Henry J S. Preparation of solid thianthrene cation radical tetrafluoroborate[J]. The Journal of Organic Chemistry, 1988, 53 21: 5142-5143. DOI:10.1021/jo00256a042.
[3] XIAO-YUE CHEN. Thianthrene Radical Cation as a Transient SET Mediator: Photoinduced Thiocyanation and Selenocyanation of Arylthianthrenium Salts?[J]. Chinese Journal of Chemistry, 2023, 41 16: 1979-1986. DOI:10.1002/cjoc.202300188.
[4] RANDY A. JOHNSON Lon J M. Synthesis and Characterization of Thianthrene-Based Polyamides[J]. Macromolecules, 1995, 28 1: 79-85. DOI:10.1021/ma00105a009. |
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