10409-06-0

Basic information

• Product Name: DIPHENYLDISULFONE
• Synonyms: DIPHENYLDISULFONE;Disulfone, diphenyl
• CAS NO: 10409-06-0
• Molecular Formula: C₁₂H₁₀O₄S₂
• Molecular Weight: 282.34
• Mol File: 10409-06-0.mol

Chemical Properties

• Boiling Point: 466.2°Cat760mmHg
• Flash Point: 300.2°C
• Appearance: /
• Density: 1.405g/cm³
• Vapor Pressure: 2.02E-08mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: DIPHENYLDISULFONE(CAS DataBase Reference)
• NIST Chemistry Reference: DIPHENYLDISULFONE(10409-06-0)
• EPA Substance Registry System: DIPHENYLDISULFONE(10409-06-0)

Safety Data

• Hazardous Substances Data: 10409-06-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 31, p. 3418, 1966 DOI: 10.1021/jo01348a514Tetrahedron Letters, 36, p. 3849, 1995 DOI: 10.1016/0040-4039(95)00653-T

InChI:InChI=1/C12H10O4S2/c13-17(14,11-7-3-1-4-8-11)18(15,16)12-9-5-2-6-10-12/h1-10H

Upstream product

• 93-59-4 Perbenzoic acid 
• 67-66-3 chloroform 
• 14758-47-5 tetrathioorthocarbonic acid tetraphenyl ester 
• 60-29-7 diethyl ether 
• 140-89-6 potassium ethyl xanthogenate 
• 98-09-9 benzenesulfonyl chloride 
• 618-41-7 Benzenesulfinic acid 
• 6272-36-2 1,2-bis(benzenesulfonyl)hydrazine 
• 599-71-3 piloty's acid 
• 882-33-7 diphenyldisulfane 
• 94-36-0 dibenzoyl peroxide 
• 7732-18-5 water 
• 151-50-8 potassium cyanide 
• 67-64-1 acetone 

Downstream Products

• 882-33-7 diphenyldisulfane 
• 98-10-2 benzenesulfonamide 

Relevant articles and documents

Electrochemical oxidation of sulfinic acids: Efficient oxidative synthesis of diaryl disulfones

Electrochemical oxidation of sulfinic acids has been studied in aqueous solutions using cyclic voltammetry, controlled-potential coulometry, chronoamperometry and chronocoulometry methods. The results indicate that the oxidation of sulfinic acids is an ir

I2-Catalyzed N-Sulfonylation of Sulfoximines with Sulfinates in Water at Room Temperature

An oxidative coupling of NH-sulfoximines and arylsulfinates catalyzed by of I2 and H2O2 affords N-sulfonyl sulfoximines. The reaction proceeds under aerobic conditions in water at room temperature. The merits of this proto

Sonochemical Preparation of Aromatic α-Disulfones

Reasonable yields (60-70percent) of aromatic α-disulfones can be obtained in short reaction times from a sonicated mixture of an arenesulfonyl chloride and lithium in THF. - Key Words: Alpha-disulfones, sonication, Wurtz-type coupling

A paradigm shift in rate determining step from single electron transfer between phenylsulfinylacetic acids and iron(III) polypyridyl complexes to nucleophilic attack of water to the produced sulfoxide radical cation: a non-linear Hammett

Mechanism of oxidative decarboxylation of phenylsulfinylacetic acids (PSAAs) by iron(III) polypyridyl complexes in aqueous acetonitrile medium has been investigated spectrophotometrically. An initial intermediate formation between PSAA and [Fe(NN)3]3+ is confirmed from the observed Michaelis–Menten kinetics and fractional order dependence on PSAA. Significant rate retardation with concentration of [Fe(NN)3]3+ is rationalized on the basis of coordination of a water molecule at the carbon atom adjacent to the ring nitrogen of the metal polypyridyl complexes by nucleophilic attack at higher concentrations. Electron-withdrawing and electron-releasing substituents in PSAA facilitate the reaction and Hammett correlation gives an upward ‘V’ shaped curve. The apparent upward curvature is rationalized based on the change in the rate determining step from electron transfer to nucleophilic attack, by changing the substituents from electron-releasing to electron-withdrawing groups. Electron-releasing substituents in PSAA accelerate the electron transfer from PSAA to the complex and also stabilize the intermediate through resonance interaction leading to negative reaction constants (ρ). Conversely, electron-withdrawing groups, while retarding the electron transfer exert an accelerating effect on the nucleophilic attack of H2O which leading to low magnitude of ρ+ compared to high ρ? values of electron-releasing groups. Marcus theory is applied, and a fair agreement is seen with the experimental values. Copyright

Tunable and Practical Synthesis of Thiosulfonates and Disulfides from Sulfonyl Chlorides in the Presence of Tetrabutylammonium Iodide

A tunable and practical synthesis of electrophilic sulfenylating reagents, thiosulfonates and disulfides, from inexpensive and easily available sulfonyl chlorides, has been developed. By appropriate choice of solvents, the reaction of sulfonyl chlorides and tetrabutylammonium iodide gave the target products in good to excellent yields, respectively. These transformations probably proceed through a reducing–coupling pathway. (Figure presented.).

Synthesis of 1,1-difluoroethylsilanes and their application for the introduction of the 1,1-difluoroethyl group

1,1-Difluoroethysilanes (R3SiCF2CH3, R = Me or Et) were synthesized from 1,1-difluoroethyl phenyl sulfone and chlorosilanes using magnesium metal via reductive 1,1-difluoroethylation. It was confirmed that 1,1-difluoroethylsilanes were effective 1,1-difluoroethylating reagents for carbonyl compounds.

Temperature-controlled selective reduction of arenesulfonyl chlorides promoted by samarium metal in DMF

Promoted by samarium in DMF, arenesulfonyl chlorides can be selectively reduced to diaryldisulfones, diarylthiosulfonates and diaryldisulfides in good to excellent yields by reaction temperature control without the need to pretreat or activate the metallic samarium.

Oxidation of thiols with hydrogen peroxide under phase transfer catalysis conditions

Theophenol was shown to be oxidized with hydrogen peroxide under conditions of phase transfer catalysis in the presence of sodium metavanadate to afford benzenesulfonic acid, diphenyl disulfide, phenyl benzenesulfonate, and diphenyl sulfone. The yield of oxidation products increases with increasing temperature, catalyst concentration, and lipophilicity of the phase transfer catalyst.

OXIDATION OF 1,2-bis-(BENZENESULFONYL)HYDRAZINE TO 1,2-DIPHENYLDISULFONE

The oxidation of 1,2-bis(benzenesulfonyl)hydrazine yields diphenyldisulfone and not 1,2-bis(benzenesulfonyl)diimide as previously reported.

OXIDATION OF DISULPHIDES BY HYDROGEN PEROXIDE IN THE PRESENCE OF SUBSTITUTED PHTHALOCYANINES OF TRANSITION METALS

A study has been made of the oxidation of disulphides of different structure by hydrogen peroxide in the presence of nitrosubstituted phthalocyanines of transition metals.It has been established that phthalocyanines in a homophase system ensure a higher initial oxidation rate of disulphides to disulphones and thiosulphonates than Na2WO4 in a two-phase system with the use of interphase transfer catalysts.