951-02-0

Basic information

• Product Name: Thianthrene, 5,10-dioxide
• Synonyms: Thianthrene, 5,10-dioxide
• CAS NO: 951-02-0
• Molecular Formula: C₁₂H₈O₂S₂
• Molecular Weight: 0
• Mol File: 951-02-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 507.1°Cat760mmHg
• Flash Point: 260.5°C
• Appearance: /
• Density: 1.63g/cm³
• Vapor Pressure: 6.6E-10mmHg at 25°C
• Refractive Index: 1.838
• CAS DataBase Reference: Thianthrene, 5,10-dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: Thianthrene, 5,10-dioxide(951-02-0)
• EPA Substance Registry System: Thianthrene, 5,10-dioxide(951-02-0)

Safety Data

• Hazardous Substances Data: 951-02-0(Hazardous Substances Data)

Usage

General Description

Thianthrene, 5,10-dioxide is a chemical compound with the molecular formula C12H8O2S2. It is a heterocyclic compound consisting of a five-membered ring fused to a six-membered ring with oxygen atoms at the 5 and 10 positions. Thianthrene, 5,10-dioxide is a versatile building block used in the synthesis of various organic compounds, including dyes and pharmaceuticals. It is known for its strong fluorescence properties, making it useful in the development of optical materials and sensors. Additionally, it has potential applications in organic electronics and as a photochromic material. Thianthrene, 5,10-dioxide is typically synthesized through oxidation of thianthrene, a related compound with a similar ring structure, and is commercially available for research and industrial use.

InChI:InChI=1/C12H8O2S2/c13-15-9-5-1-2-6-10(9)16(14)12-8-4-3-7-11(12)15/h1-8H

Upstream product

• 2362-50-7 thianthrene-5-oxide 
• 40053-29-0 S-phenyl 3-oxobutanethioate 
• 29577-53-5 2-Methoxy-benzaldehyde oxime 
• 35787-71-4 thianthrene cation radical perchlorate 
• 3717-21-3 p-methoxyl benzaldoxime 

Downstream Products

• 92-85-3 Thianthrene 

Relevant articles and documents

Oxygen transfer reactions. 2. A comparison of the reactions of ruthenium tetroxide, chromyl chloride, and permanganate with thianthrene 5-oxide

Products obtained from the oxidation of thianthrene 5-oxide, SSO, have been used to compare oxygen transfer mechanisms for three high-valent transition metals. Oxidation of SSO by benzyltriethylammonium permanganate in methylene chloride gives the corresponding sulfone, thianthrene 5,5-dioxide (SSO2), as the exclusive product. Oxidation of SSO by ruthenium tetroxide also gives SSO2 as the predominant product along with minor amounts of the disulfoxide, thianthrene 5,10-dioxide (SOSO). However, the converse is observed when chromyl chloride is used as the oxidant; SOSO is the major product. It is suggested that oxygen transfers from permanganate and ruthenium tetroxide are initiated by complexation between the central metal atom and the oxygen end of the S=O dipole, while oxidation by chromyl chloride is likely initiated by an alternative mechanism, possibly a single electron transfer.

Synthesis of 2H-1-Benzothiopyran-2-ones (Thiocoumarins) and Related Compounds from Benzenethiols and Diketene

The products formed by the reaction of benzenethiols with diketene in the presence of H2SO4 are (E)-β-(arylthio)crotonic acids (2) and/or isomeric (Z)-β-(arylthio)crotonic acids and not, as has been reported, S-phenyl-3-oxobutanethioates (1).Compounds 1a-k, as the precursor of thiocoumarins, were prepared from benzenethiols and diketene in the presence of triethylamine.The reaction of 1 with various condensing agents has been examined to prepare 2H-1-benzothiopyran-2-ones (thiocoumarins).It is found that 4-methyl(thiocoumarins) were conveniently prepared by thereaction of 1 with anhydrous aluminium chloride in yields of 16-48percent.When 1 was treated with PPA, isomeric 2-methyl(thiochromones) were preferentially obtained in yields of 5-66percent, and compound 2 was isolated as an intermediate.The spectral characteristics of 4-methyl(thiocoumarins) have also been described.