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

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

Uses

Used in Organic Synthesis:
Thianthrene, 5,10-dioxide is utilized as a key building block in the synthesis of a wide range of organic compounds. Its unique structure and properties make it valuable for creating dyes and pharmaceuticals, contributing to the development of new and improved products in these fields.
Used in Optical Materials and Sensors:
Leveraging its strong fluorescence properties, Thianthrene, 5,10-dioxide is employed in the development of optical materials and sensors. Its ability to emit light under certain conditions allows for its use in creating advanced sensor technologies and materials with specific light-emitting characteristics.
Used in Organic Electronics:
Thianthrene, 5,10-dioxide's potential applications extend to the field of organic electronics, where its electronic properties can be harnessed to improve the performance of electronic devices and components.
Used as a Photochromic Material:
Due to its ability to change its properties in response to light, Thianthrene, 5,10-dioxide is used as a photochromic material. This application is particularly relevant in industries that require materials that can adapt their optical properties based on light exposure, such as smart windows or optical data storage.
Thianthrene, 5,10-dioxide is typically synthesized through the 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

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

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.

Reactions of Oximes with Thianthrene Cation Radical in Nitrile Solvents. Cycloaddition To Form Oxadiazoles and Deoxygenation To Form Nitriles

Reactions of eight oximes, RCH=NOH (1a, R= C6H5; 1b, R= 4-CH3C6H4; 1c, R= 4-NO2C6H4; 1d, R= 4-CH3OC6H4; 1e, R= 2-CH3OC6H4; 1f, R= 1-naphthyl; 1g, R= C5H11; 1h, R= C4H9), with thianthrene cation radical perchlorate (Th.+ClO4-) in acetonitrile under argon were studied.The major product from the oxime in all cases, but of 1d, was the nitrile, RCN.The anticipated product of oxidative cycloaddition, namely, a 3-R-5-methyl-1,2,4-oxadiazole (2), was obtained in substantial yield (2d, 66percent) only in the case of 1d.An isomeric 5-R-3-methyl-1,2,4-oxadiazole (3) was obtained from some reactions, that is, 3c alone from 1c, and a mixture of 2a and 3a from 1a.Neither 2 nor 3 was obtained in measurable amounts from reactions of 1g and 1h.The aldehyde (RCHO) was obtained in small yields from each reaction.Thianthrene (Th) and thianthrene 5-oxide (ThO) were also major products.Studies with -1b and -1d showed that the oxgen atom in 2 came entirely and in ThO primarily from the oxime.Studies of workup with H218O showed that the workup water was the source of the oxgen atom in RCHO and to a small extent in ThO.Explanations are given for the formation of 2 by a stepwise addition of RCH=NOH.+ (1.+) to solvent nitrile and of 3 by the reaction of solvent nitrile with an oxaziridine cation radical (7, obtained from 1.+).

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.