Thianthrene Chemical Properties

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

CAS DataBase Reference

92-85-3(CAS DataBase Reference)

NIST Chemistry Reference

Thianthrene(92-85-3)

EPA Substance Registry System

Thianthrene (92-85-3)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29349990

MSDS

• Language:English Provider:Thianthrene
• Language:English Provider:SigmaAldrich

Thianthrene Usage And Synthesis

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: Thianthrene is 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. It is a mancude organic heterotricyclic parent, an organosulfur heterocyclic compound and a member of thianthrenes.

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.

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.

Thianthrene(92-85-3)Related Product Information

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