92-85-3

Basic information

• Product Name: Thianthrene
• Synonyms: THIANTHRENE;AKOS 90207;DIPHENYLENE DISULFIDE;DI-O-PHENYLENE DISULFIDE;9,10-Dithiaanthracene;dibenzo-1,4-dithiin;Thiaanthrene;Thianthren
• CAS NO: 92-85-3
• Molecular Formula: C₁₂H₈S₂
• Molecular Weight: 216.32
• EINECS: 202-197-0
• Product Categories: Xanthones;Heterocyclic Building Blocks;Others;S-Containing
• Mol File: 92-85-3.mol

Chemical Properties

• Melting Point: 151-155 °C(lit.)
• Boiling Point: 364-366 °C(lit.)
• Flash Point: 170.8 °C
• Appearance: White or slight yellow powder
• Density: 1.4420
• Vapor Pressure: 0.000128mmHg at 25°C
• Refractive Index: 1.6210 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: DMF: soluble
• BRN: 83046
• CAS DataBase Reference: Thianthrene(CAS DataBase Reference)
• NIST Chemistry Reference: Thianthrene(92-85-3)
• EPA Substance Registry System: Thianthrene(92-85-3)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 92-85-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research:
Thianthrene is used as a research compound for studying the aqueous solubilities of several solid nitrogen-, sulfur-, and oxygen-containing heterocyclic derivatives of anthracene, phenanthrene, and fluorene. This helps in understanding the solubility behavior of these compounds in different solvents and their potential applications.
Used in Analytical Chemistry:
Thianthrene is employed in the determination of partition coefficients of several sulfur-containing aromatics in 1-hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide and supercritical carbon dioxide. This aids in understanding the distribution of these compounds between different phases and their potential use in various industries.

Synthesis Reference(s)

The Journal of Organic Chemistry, 31, p. 4071, 1966 DOI: 10.1021/jo01350a045

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.]

InChI:InChI=1/C12H8S2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8H

Upstream product

• 109-72-8 n-butyllithium 
• 2362-50-7 thianthrene-5-oxide 
• 60-29-7 diethyl ether 
• 626-04-0 3-mercaptothiophenol 
• 139-66-2 diphenyl sulfide 
• 16854-72-1 Dithiomalonsaeure-S,S'-diphenylester 
• 154341-96-5 thianthrene-2,7-dicarboxylic acid 
• 595-90-4 tetraphenyltin(IV) 
• 87797-73-7 di-(o-iodophenyl) disulfide 
• 6764-13-2 2-aminodiphenyl sulfide hydrochloride 
• 120-80-9 benzene-1,2-diol 
• 108-98-5 thiophenol 
• 95-50-1 1,2-dichloro-benzene 
• 882-33-7 diphenyldisulfane 

Downstream Products

• 49820-01-1 2-(thianthrene-2-carbonyl)-benzoic acid 
• 18866-40-5 triphenyl-thianthren-1-yl-silane 
• 53455-06-4 2-Bromothianthrene 
• 2362-55-2 thianthrene-5,5,10,10-tetraoxide 
• 71-43-2 benzene 
• 110361-46-1 p-cyanobenzylthianthrenesulfonium trifluoromethanesulfonate 
• 84-15-1 o-terphenyl 
• 95-47-6 o-xylene 
• 2388-68-3 o-bis(mercaptomethyl)benzene 
• 132-65-0 dibenzothiophene 
• 92-52-4 biphenyl 
• 2362-50-7 thianthrene-5-oxide 
• 824-69-1 2,5-dichloro-1,4-hydroquinone 
• 92-85-3 thianthrene cation radical 

Relevant articles and documents

Isotopically Selective Electron Transfer between Free Radical Cations and their Parent Molecules Enables Isotope Enrichment

Electron transfer between the thianthrene radical cation and its neutral molecule precursor shows a significant H/D equilibrum isotope effect which may be used for isotopic enrichment.

Electron Transfer Rates in Highly Exothermic Reactions on Semiconductor-Electrolyte Interfaces, and the Deuterium Isotope Effect

Highly exothermic electron transfer rates were measured by semiconductor electrochemical techniques.Experiments demonstrate that the decreases in the electron transfer rates with the exothermicity of the reactions in so-called abnormal regions are much more moderate than the classical predictions, and that this is probably due to the effects of intramolecular vibrations such as C-H stretching and/or bending.

Regio- and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles

Herein, we report a regioselective alkenyl electrophile synthesis from unactivated olefins that is based on a direct and regioselective C?H thianthrenation reaction. The selectivity is proposed to arise from an unusual inverse-electron-demand hetero-Diels–Alder reaction. The alkenyl sulfonium salts can serve as electrophiles in palladium- and ruthenium-catalyzed cross-coupling reactions to make alkenyl C?C, C?Cl, C?Br, and C?SCF3 bonds with stereoretention.

CHEMISTRY ON BENZOPENTATHIEPIN. REACTIONS OF BENZOPENTATHIEPIN WITH AROMATIC COMPOUNDS IN THE PRESENCE OF LEWIS ACID

Benzopentathiepin (BPT) reacted with many aromatic compounds such as benzene, 1,4-dimethylbenzene, and naphthalene in the presence of Lewis acid to give various thianthrenes in moderate yields, BPT was found to serve as a 1,4-dication synthon.

Synthesis of 1- and 2-substituted thianthrenes

Lithiation of thianthrene at C-1 allows the synthesis of various 1-substituted thianthrenes for example thianthren-1-ylboronic acid and 1-tributylstannylthianthrene, which undergo palladium-catalysed couplings with aryl halides. 2-Bromothianthrene provides an entry to 2-substituted thianthrenes via lithium-halogen exchange then reaction of 2-lithiothianthrene with electrophiles including formation of the 2-boronic acid and 2-tributylstannylthianthrene which were coupled to aryl halides.

2,3,8,9-Dibenzo-5,6-(substituted)benzo-1,4-dithio-7-azacyclonona-2,5,8- trienes. Synthesis and Mechanistic Study

5-(2-Acetamidoaryl)thianthreniumyl perchlorates reacted with potassium hydroxide in methanol at reflux giving 2,3,8,9-dibenzo-5,6-(substituted)benzo-1,4-dithio-7-azacyclonona-2,5,8-trienes 4 in 43 to 75% yields, whereas the reactions of the same compounds with sodium hydride in the absence or in the presence of dimethyl sulfate in refluxing tetrahydrofuran gave N-acetylated and N-methylated 4 in 68 to 96% and 27 to 56% yields, respectively. The mechanism of the formation of the products might be explained by a nucleophilic attack of amide ions 10, 12, and 14 at the ispo-position of the thianthrene ring. A sulfuranyl radical mechanism might be involved in these reactions.

Addition of Thianthrene Cation Radical to Cycloalkenes. An Unexpected Monoadduct

Whereas the addition of thianthrene cation radical perchlorate (Th?+ClO4-) to cyclohexene gives a bisadduct, namely, trans-1,2-bis(5-thianthreniumyl)cyclohexane diperchlorate (1), and additon to other alkenes and alkynes also gives trans-bisadducts, addition to cyclooctene gave only a cis-monoadduct, namely, 1,2-(5,10-thianthreniumdiyl)cyclooctane diperchlorate (2a). Similar monoadducts 2b-d were obtained from the addition of Th?+BF4-, Th?+SbF6-, and Th?+PF6- to cyclooctene. The structure of the monoadduct was deduced from its 1H and 13C NMR spectra, from the stoichiometry of its formation, and from the stoichiometry of its reaction with NaSPh, which gave equimolar amounts of cyclooctene, thianthrene, and diphenyl disulfide. The structure was confirmed with X-ray crystallography. Addition of Th?+ salts to cyclopentene and cycloheptene gave mixtures of mono- and bisadducts. The bisadduct of Th?+SbF6- to cyclopentene, separated from the small amount of monoadduct by crystallization, was shown with X-ray crystallography to have the trans configuration.

Exploiting amphiphilicity: Facile metal free access to thianthrenes and related sulphur heterocycles

Benzodithioloimines are reacted with arynes or alkynes substituted with electron-withdrawing groups to afford the corresponding thianthrene or benzo[b][1,4]dithiine derivatives. The transformation takes place under mild reaction conditions without any transition metal. Furthermore, the reaction mode could be expanded to 2-thiocyanatopyrroles yielding pyrrolothiazoles.

Allylic Amination of Alkenes with Iminothianthrenes to Afford Alkyl Allylamines

Allylic C-H amination is currently accomplished with (sulfon)amides or carbamates. Here we show the first allylic amination that can directly afford alkyl allylamines, enabled by the reactivity of thianthrene-based nitrogen sources that can be prepared from primary amines in a single step.

Organic compound, electronic device and electronic device (by machine translation)

The present application relates to an organic compound, and containing an electronic device containing the organic compound and an electronic device, containing the organic compound, wherein the organic compound, main body is shown as a large planar structure, in a steric space by introducing an electron rich arylamine or a heteroarylamine substituent, at 9 position of the fluorene or the silicon fluorenyl group such that the hole transport performance of the compound is excellent. (by machine translation)