2362-55-2

Basic information

• Product Name: thianthrene 5,5,10,10-tetraoxide
• Synonyms: Thianthrene 5,5,10,10-tetraoxide
• CAS NO: 2362-55-2
• Molecular Formula: C₁₂H₈O₄S₂
• Molecular Weight: 280.3195
• Mol File: 2362-55-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 545.8°C at 760 mmHg
• Flash Point: 379.1°C
• Density: 1.564g/cm³
• Vapor Pressure: 2.04E-11mmHg at 25°C
• Refractive Index: 1.671
• CAS DataBase Reference: thianthrene 5,5,10,10-tetraoxide(CAS DataBase Reference)
• NIST Chemistry Reference: thianthrene 5,5,10,10-tetraoxide(2362-55-2)
• EPA Substance Registry System: thianthrene 5,5,10,10-tetraoxide(2362-55-2)

Safety Data

• Hazardous Substances Data: 2362-55-2(Hazardous Substances Data)

Usage

General Description

Thianthrene 5,5,10,10-tetraoxide is a chemical compound with the molecular formula C8H4O4. It is a yellow to orange solid that is insoluble in water and has a melting point of around 210-215°C. Thianthrene 5,5,10,10-tetraoxide is a powerful oxidizing agent and can react violently with reducing agents. It is primarily used as a reagent in organic synthesis, particularly in the oxidation of organic compounds. Thianthrene 5,5,10,10-tetraoxide is also known to have mutagenic and carcinogenic properties, and it should be handled with extreme caution in laboratory and industrial settings.

Upstream product

• 7664-93-9 sulfuric acid 
• 7732-18-5 water 
• 7722-84-1 dihydrogen peroxide 
• 92-85-3 Thianthrene 
• 71-43-2 benzene 
• 2362-50-7 thianthrene-5-oxide 
• 2362-54-1 thianthrene-5,5,10-trioxide 

Downstream Products

• 244-98-4 Dibenzotellurophen 
• 1016-05-3 dibenzothiophene sulfone 
• 2362-53-0 thianthrene 5,5-dioxide 
• 861606-26-0 2-(2-ethoxy-benzenesulfonyl)-benzenesulfinic acid 
• 262-30-6 selenanthrene 
• 92-85-3 Thianthrene 
• 92-52-4 biphenyl 
• 71-43-2 benzene 
• 244-95-1 dibenzo[b,d]selenophene 

Relevant articles and documents

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Metal and solvent free selective oxidation of sulfides to sulfone using bifunctional ionic liquid [pmim]IO4

The oxidation of organo-sulfides to sulfones has been accomplished using an easily accessible bifunctional ionic liquid, [pmim]IO4 in the absence of any other oxidants, metal and organic solvent at ambient temperature. A variety of sulfides including dialkyl, aryl-alkyl, diaryl, and aryl-hetero aryl have been oxidized to the corresponding functionalized sulfones in high yields by this procedure.

The Relative Reactivity of Thioethers and Sulfoxides toward Oxygen Transfer Reagents: The Oxidation of Thianthrene 5-Oxide and Related Compounds by MoO5HMPT

The oxidation of thianthrene 5-oxide (SSO) by MoO5HMPT has been studied in 1,2-dichloroethane at 40 deg C.Under conditions of excess substrate over the oxidant, three products are formed, i.e., two isomeric cis and trans bissulfoxides (SOSO) and sulfide-sulfone (SSO2) which quantitatively account for the active oxygen of MoO5HMPT consumed.The rates of appearance of the products at different reactant concentrations have been measured.A second-order rate law has been established.The ratios of the rate constants and of the final concentrations of the three products, i.e., k2(cis-SOSO):k2(trans-SOSO):k2(SSO2) = 1.0:4.0:1.0; infinite:infinite:infinite = 1.0:4.5:1.2, are in good agreement.The trans-SOSO-forming reaction is only 4-fold faster than that leading to SSO2. cis-SOSO and SSO2 are produced at almost the same rate.Evidence is presented that all the oxidation reactions are electrophilic processes taking place via a simple bimolecular mechanism not involving the coordination of the substrate to the metal.The low selectivity is due to the scarce reactivity of the thioether center in thianthrene 5-oxide.The investigation of the oxidative behavior of structurally related compounds reveals that such a low reactivity results from a combination of stereoelectronic effects.These findings provide a rationale to some ambiguous results obtained when thianthrene 5-oxide is employed as a mechanistic probe of the electronic character of the oxidants.

FURTHER FUNCTIONAL GROUP OXIDATIONS USING SODIUM PERBORATE

Sodium perborate in acetic acid is an effective reagent for the oxidation of aromatic aldehydes to carboxylic acids, iodoarenes to (diacetoxyiodo)arenes, azines to N-oxides, and various types of sulfur heterocycles to S,S-dioxides.Nitriles are unaffected by the reagent in acetic acid, but undergo smooth hydration to amides when aqueous methanol is employed as solvent.