3085-42-5

Usage

Chemical Properties

SLIGHTLY YELLOW TO LIGHT BEIGE FINE CRYST. POWDER

Safety Profile

A poison by intravenous route.Moderately toxic by intraperitoneal route. When heated todecomposition it emits toxic vapors of NOx and Cl-.

InChI:InChI=1/C12H8Cl2OS/c13-9-1-5-11(6-2-9)16(15)12-7-3-10(14)4-8-12/h1-8H

Upstream product

• 5181-10-2 bis(4-chlorophenyl)sulfide 
• 24824-20-2 dichloro-bis-(4-chloro-phenyl)-λ⁴-sulfane 
• 108-90-7 chlorobenzene 
• 1016-82-6 1-benzenesulfinyl-4-chloro-benzene 
• 106-48-9 4-chloro-phenol 
• 139-66-2 diphenyl sulfide 
• 1013-23-6 Dibenzothiophene sulfoxide 
• 5285-87-0 phenyl thiocyanate 
• 108-88-3 toluene 
• 71-43-2 benzene 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 637-87-6 1-Chloro-4-iodobenzene 
• 7732-18-5 water 

Downstream Products

• 5181-10-2 bis(4-chlorophenyl)sulfide 
• 125428-43-5 tris(4-chlorophenyl)sulfonium bromide 
• 83373-39-1 trans-4-guanidinomethylcyclohexanecarboxylic acid p-chlorophenyl ester hydrochloride 
• 80-07-9 4,4'-dichlorodiphenyl sulphone 
• 95-57-8 2-monochlorophenol 
• 106-48-9 4-chloro-phenol 
• 106-46-7 para-dichlorobenzene 
• 1308853-73-7 ethyl 1-(5-chloro-2-(4-chlorophenylthio)phenyl)-2-oxocyclohexanecarboxylate 
• 7205-72-3 (4-chlorophenyl) isopropyl sulfoxide 
• 555-16-8 4-nitrobenzaldehdye 

Relevant academic research and scientific papers

Iron(III) chloride (FeCl3)-catalyzed electrophilic aromatic substitution of chlorobenzene with thionyl chloride (SOCl2) and the accompanying auto-redox in sulfur to give diaryl sulfides (Ar2S): Comparison to catalysis by aluminum chloride (AlCl3)

The Lewis acids MCl3(M = Fe and Al)-catalyzed electrophilic aromatic (ArH) substitution reactions with thionyl chloride (SOCl2) have been shown to give diaryl sulfoxide (Ar2SO) and the reduced diaryl sulfide (Ar2S). Under various selected conditions, the FeCl3-catalyzed reactions of chlorobenzene gave substantially much higher percent yields of Ar2S (Ar = p-ClC6H4) than the reactions catalyzed by AlCl3, showing that FeCl3facilitates the reduction in the sulfur center of SOCl2. A dπ?>pπ*back bond between Fe(III) and the O?S group is thought to be responsible for enhancement of the reduction.

Ni-Catalyzed Borylation of Aryl Sulfoxides

A nickel/N-heterocyclic carbene (NHC) catalytic system has been developed for the borylation of aryl sulfoxides with B2(neop)2 (neop=neopentyl glycolato). A wide range of aryl sulfoxides with different electronic and steric properties were converted into the corresponding arylboronic esters in good yields. The regioselective borylation of unsymmetric diaryl sulfoxides was also feasible leading to borylation of the sterically less encumbered aryl substituent. Competition experiments demonstrated that an electron-deficient aryl moiety reacts preferentially. The origin of the selectivity in the Ni-catalyzed borylation of electronically biased unsymmetrical diaryl sulfoxide lies in the oxidative addition step of the catalytic cycle, as oxidative addition of methoxyphenyl 4-(trifluoromethyl)phenyl sulfoxide to the Ni(0) complex occurs selectively to give the structurally characterized complex trans-[Ni(ICy)2(4-CF3-C6H4){(SO)-4-MeO-C6H4}] 4. For complex 5, the isomer trans-[Ni(ICy)2(C6H5)(OSC6H5)] 5-I was structurally characterized in which the phenyl sulfinyl ligand is bound via the oxygen atom to nickel. In solution, the complex trans-[Ni(ICy)2(C6H5)(OSC6H5)] 5-I is in equilibrium with the S-bonded isomer trans-[Ni(ICy)2(C6H5)(SOC6H5)] 5, as shown by NMR spectroscopy. DFT calculations reveal that these isomers are separated by a mere 0.3 kJ/mol (M06/def2-TZVP-level of theory) and connected via a transition state trans-[Ni(ICy)2(C6H5)(η2-{SO}-C6H5)], which lies only 10.8 kcal/mol above 5.

PROCESS FOR PRODUCING 4,4'-DICHLORODIPHENYL SULFONE

The invention relates to a process for producing 4,4'-dichlorodiphenyl sulfone, comprising: (I) reacting thionyl chloride, chlorobenzene and aluminum chloride forming an intermediate reaction product and hydrogen chloride; (II) mixing aqueous hydrochloric acid and the intermediate reaction product to obtain an organic phase comprising 4,4'-dichlorodiphenyl sulfoxide and an aqueous phase; (III) cooling the organic phase to a temperature below the saturation point of 4,4'- dichlorodiphenyl sulfoxide to obtain a suspension; (IV) solid-liquid-separation of the suspension to obtain crystallized 4,4'-dichlorodiphenyl sulfoxide, and mother liquor; (V) washing the crystallized 4,4'-dichlorodiphenyl sulfoxide with a carboxylic acid to obtain carboxylic acid-wet 4,4'-dichlorodiphenyl sulfoxide; (VI) reacting the washed 4,4'-dichlorodiphenyl sulfoxide and an oxidizing agent in a carboxylic acid as solvent to obtain a reaction mixture comprising 4,4'-dichlorodiphenyl sulfone and carboxylic acid; (VII) separating the reaction mixture comprising 4,4'-dichlorodiphenyl sulfone and carboxylic acid into a residual moisture comprising 4,4'-dichlorodiphenyl sulfone as crude product and a liquid phase comprising carboxylic acid.

(C)CRYSTAL COMPOSITION (CC) COMPRISING 4,4'-DICHLORODIPHENYLSULFONE CRYSTALS (C)

The invention relates to crystals (C) consisting of at least 98 % by weight of 4,4'- dichlorodiphenylsulfone, 0 to 2 % by weight of impurities and 0 to 2 % by weight of at least one solvent (c). Moreover, the present invention relates to a crystal composition (CC) comprising crystals (C) and a process for the production of the crystal composition (CC) and the crystals (C).

Selective synthesis of sulfoxides and sulfonesviacontrollable oxidation of sulfides withN-fluorobenzenesulfonimide

A practical and mild method for the switchable synthesis of sulfoxides or sulfonesviaselective oxidation of sulfides using cheapN-fluorobenzenesulfonimide (NFSI) as the oxidant has been developed. These highly chemoselective transformations were simply achieved by varying the NFSI loading with H2O as the green solvent and oxygen source without any additives. The good functional group tolerance makes the strategy valuable.

Photocatalytic Activity of Ruthenium(II) Complex with 1,10-Phenanthroline-3,8-dicarboxylic Acid in Aerobic Oxidation Reactions

Abstract: Mixed-ligand ruthenium(II) complex with 2,2′-bipyridine and 1,10-phenanthroline-3,8-dicarboxylic acid with the composition [Ru(phen-C)(bpy)2]Cl2·5H2O (bpy = 2,2′-bipyridine, phen-C = 1,10-phenantroline-3,8-dicarboxylic acid) has been synthesized and characterized by spectral data. The complex has been tested as photocatalyst in aerobic oxidation reactions, including transformation of arylboronic acids to phenols, primary amines to imines, and sulfides to sulfoxides in aqueous medium. The possibility of regeneration of the catalyst in the oxidation of sulfides has been demonstrated.

PROCESS FOR PRODUCING 4,4`-DICHLORODIPHENYL SULFOXIDE

The invention relates to a process for producing 4,4'-dichlorodiphenyl sulfoxide comprising: (I) reacting thionyl chloride, chlorobenzene and aluminum chloride in a molar ratio of thionyl chloride : chlorobenzene : aluminum chloride of 1 : (6 to 9) : (1 to 1.5) at a temperature in the range from 0 to below 20°C, forming an intermediate reaction product and hydrogen chloride; (II) mixing aqueous hydrochloric acid and the intermediate reaction product at a temperature in the range from 70 to 110°C to obtain an organic phase comprising 4,4'-dichlorodiphenyl sulfoxide and an aqueous phase; (III) cooling the organic phase comprising the 4,4'-dichlorodiphenyl sulfoxide to a temperature below the saturation point of 4,4'-dichlorodiphenyl sulfoxide to obtain a suspension comprising crystallized 4,4'-dichlorodiphenyl sulfoxide; (IV) solid-liquid-separation of the suspension to obtain a residual moisture containing solid 4,4'-dichlorodiphenyl sulfoxide comprising crystallized 4,4'-dichlorodiphenyl sulfoxide and mother liquor.

Preparation method for catalytic synthesis 4 and 4 ’ -dichlorophenylsulfone (by machine translation)

A catalyst, chlorobenzene and thionyl chloride 4 are 4 ’ - subjected to a Fourier reaction under the action of catalyst, chlorobenzene and thionyl chloride are subjected to a Fourier reaction under the action of a catalyst pH value is poured into reaction liquid to obtain '- dichlorodiphenyl sulfoxide, then the reaction solution is cooled down to devitrification and filtered to obtain' - dichlorodiphenyl sulfone 4,4 . 0 - 5 °C 4,4The product has the advantages of simple process, low cost, less impurities, high purity of the obtained product, less than 99.2percent, 2 and 4 ’ isomer content, more than 0.1percent, good economic benefit and suitability for industrial production 90percent. (by machine translation)

Selective oxidation of (hetero)sulfides with molecular oxygen under clean conditions

The development of eco-friendly and switchable catalytic systems for the conversion of a sole raw-material into distinct high-value products is a particularly attractive concept and a daunting synthetic challenge. In the present work, the first example of efficient and selective oxidation of sulfides to sulfones and sulfoxides using molecular oxygen under clean conditions was established.

Synthesis and nano-Pd catalyzed chemoselective oxidation of symmetrical and unsymmetrical sulfides

A highly chemoselective, efficient and nano-Pd catalyzed protocol for the rapid construction of sulfoxides and sulfones via the oxidation of symmetrical and unsymmetrical sulfides using H2O2 as an oxidant has been developed, respectively. The ready availability of starting materials, easy recovery and reutilization of the catalyst, wide substrate scope, and high yields make this protocol an attractive alternative. The process also involves the metal-free and microwave-promoted synthesis of symmetrical diarylsulfides, and FeCl3-mediated preparation of symmetrical diaryldisulfides through the reaction of arenediazonium tetrafluoroborates with Na2S·9H2O as a sulfur source. In addition, unsymmetrical sulfides were generated via the K2CO3-mediated reaction of arenediazonium tetrafluoroborates with symmetrical disulfides.