84355-05-5

Usage

Chemical class

Sulfone-based compound

Structure

Contains a benzene ring substituted with a chloro group and a sulfonylmethyl group attached to a phenyl ring

Usage

Often used as a precursor in the synthesis of various drugs and pesticides

Potential

Building block in organic synthesis and pharmaceutical research

Applications

Potential applications in medicinal chemistry and drug development

Hazards

May have hazardous properties and should be handled with care by trained professionals in a controlled laboratory environment.

Upstream product

• 23566-23-6 1,1’-[thiobis(methylene)]bis[4-chlorobenzene] 
• 622-95-7 4-chlorobenzyl bromide 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 

Downstream Products

• 874512-60-4 2,5-bis-(4-chloro-phenyl)-1,1-dioxo-1λ⁶-thiophene-3,4-diol 

Relevant academic research and scientific papers

A new series of Ni(II), Cu(II), Co(II) and Pd(II) complexes with an ONS donor Schiff base: Synthesis, crystal structure, catalytic properties and bioactivities

A new series of bichelated complexes of the formula M(L)2 and M(L)Cl, where M = Ni(II), Cu(II), Co(II) and Pd(II) and L = a deprotonated Schiff base, were synthesized from the reaction of 5-bromo N-[(2-benzylthio)- phenyl] salicylaldimine (HL, 1), a new potential tridentate (O, N, S donor) Schiff base, with metal salts in methanol medium, and the complexes were characterized by a variety of physicochemical techniques, namely elemental analyses, FT-IR, 1H NMR and UV-Vis spectroscopies, thermogravimetric analysis and conductivity studies. The coordination mode of the palladium complex was determined by single crystal X-ray diffraction studies and was found to possess a distorted square planar structure with the ligand coordinated as a uninegatively charged tridentate chelating agent via the hydroxyl oxygen, azomethine nitrogen and thioether sulfur atoms, and the remaining fourth coordinating site was filled by a chloride ion. The copper complex shows very good catalytic activities towards the oxidation of organic thioethers to the corresponding sulfoxide and sulfones using H2O2 as the oxidant. The ligand and complexes exhibited considerable antibacterial and antifungal activities against Klebsiella pneumoniae (ATCC 10536), Staphylococcus aureus (ATCC 11632) and Candida albicans.

A simple and efficient direct method for the synthesis of symmetric dibenzyl sulfones from sodium dithionite and benzyl chlorides in ionic liquid

Symmetric dibenzyl sulfones were synthesized in ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim]BF4) at 100°C from various benzyl chlorides and sodium dithionite in moderate yields.

Organic Reactions of Reduced Species of Sulfur Dioxide

Rongalite (sodium hydroxymethanesulfinate or sodium formaldehydesulfoxylate) reacts with organic halides in a variety of ways depending on the structure of the organic compound.Benzyl and other alkyl halides give sulfones in generally good yields; but in several cases, reduction (2,4-dinitrobenzyl bromide, phenacyl halides) or coupling (p-nitrobenzyl bromide under basic conditions, phenacyl bromide or iodide) of the halide occurs.Addition of sodium iodide to the mixture of Rongalite and phenacyl chloride changed the reaction from one of complete reduction to acetophenone to one of mainly dimerization to 1,4-diphenyl-1,4-butanedione.The amount of acetophenone from phenacyl bromide depends on the water content of the reaction mixture, more dimer being formed when little water is present.Diphenacyl sulfone is formed from phenacyl bromide and Rongalite in the presence of excess sulfur dioxide.The intermediate β-keto sulfinate is believed to normally lose sulfur dioxide very readily to give the enolate anion, which either is protonated to give acetophenone or reacts with phenacyl halide to give the butanedione.In the presence of excess sulfur dioxide, the loss of sulfur dioxide from the sulfinate is supressed, allowing sulfone formation to occur by reaction of the sulfinate with phenacyl halide. o-Xylylene dibromide gave o-xylylene, trapped as the Diels-Alder adduct with norbornene, along with the expected cyclic sulfone and cyclic sulfinate ester (sultine).A convenient synthesis of the sultine in 78percent yield is achieved by treatment of α,α'-dichloro-o-xylene with Rongalite and sodium iodide.Treatment of Rongalite in DMF-H2O with sulfur dioxide gives the blue anion radical complex (SO2)(SO2.-).Anion radicals are produced from p-dinitrobenzene and p-nitrobenzoate ion when they are treated with Rongalite.

A SIMPLE, ONE STEP, PROCEDURE FOR THE PREPARATION OF DIBENZYL SULPHONES FROM BENZYL HALIDES

Sodium formaldehyde sulphoxylate is shown to be a useful reagent for the conversion of benzyl halides to dibenzyl sulphones.

NOVEL ADDUCTS OF SULFIDES AND 4-SUBSTITUTED 1,2,4-TRIAZOLINE-3,5-DIONES ( TAD )- A SIMILARITY OF TAD AND SINGLET OXYGEN ( 1O2 ) -

The 4-substituted 1,2,4-triazoline-3,5-diones( 2 ) afford with sulfides( 1 ) having acidic α-hydrogens the 1,4-disubstituted urazoles( 3 ).Reactivity of the triazoline-dione shows similarity in possible reaction modes with that of singlet oxygen.