1535-65-5

Usage

Uses

Used in Pharmaceutical Industry:
[(Difluoromethyl)sulfonyl]benzene is used as an efficient reagent for the difluoromethylation of carbonyls and aldehydes, which is crucial in the synthesis of various pharmaceutical compounds. Its ability to selectively introduce difluoromethyl groups into target molecules enhances the biological activity and pharmacokinetic properties of the resulting drugs.
Used in Organic Chemistry Research:
In the field of organic chemistry, [(Difluoromethyl)sulfonyl]benzene serves as a reagent for the nucleophilic difluoro(phenylsulfonyl)methylation of carbonyls. This reaction is essential for the synthesis of complex organic molecules and contributes to the development of new chemical compounds with potential applications in various industries.
Used in Chemical Synthesis:
[(Difluoromethyl)sulfonyl]benzene is also used in chemical synthesis processes, where its unique properties allow for the creation of novel compounds with specific functional groups. These synthesized compounds can be utilized in various applications, such as agrochemicals, materials science, and specialty chemicals.

InChI:InChI=1S/C7H6F2O2S/c8-7(9)12(10,11)6-4-2-1-3-5-6/h1-5,7H

Upstream product

• 1535-67-7 difluoromethyl phenyl sulfide 
• 75-45-6 Chlorodifluoromethane 
• 873-55-2 sodium benzenesulfonate 
• 1717-59-5 2,2-difluoro-2-(fluorosulfonyl)acetic acid 
• 1193-82-4 racemic methyl phenyl sulfoxide 
• 536975-50-5 [difluoro(phenylsulfonyl)methyl](trimethyl)silane 
• 536975-49-2 phenyl (trimethylsilyl)difluoromethyl sulfide 
• 108-98-5 thiophenol 
• 80351-58-2 [(bromodifluoromethyl)sulfonyl]benzene 
• 1073-67-2 4-vinylbenzyl chloride 
• 1042681-48-0 (3E)-1,1-difluoro-2,4-diphenyl-1-(phenylsulfonyl)but-3-en-2-ol 
• 3112-85-4 methylphenylsulfonate 
• 22235-34-3 phenylsulfonyldifluoroacetic acid 
• 100-52-7 benzaldehyde 

Downstream Products

• 359-15-9 difluoromethyl methyl ether 
• 1535-67-7 difluoromethyl phenyl sulfide 
• 618-41-7 Benzenesulfinic acid 
• 98-00-0 (2-furyl)methyl alcohol 
• 122590-90-3 α-(difluoromethyl)-2-furanmethanol 
• 122590-93-6 (difluoro(phenylsulfonyl)methyl)(phenyl)sulfane 
• 142887-91-0 1-[(2R,3aR,9aR)-3-(Benzenesulfonyl-difluoro-methyl)-3-hydroxy-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl]-4-ethoxy-1H-pyrimidin-2-one 
• 122590-88-9 2,2-difluoro-1-(4-methylphenyl)-2-phenylsulfonylethanol 
• 122590-89-0 1-(4-chlorophenyl)-2,2-difluoro-2-(phenylsulfonyl)ethan-1-ol 
• 122590-87-8 2,2-difluoro-1-(4-methoxyphenyl)-2-(phenylsulfonyl)ethan-1-ol 
• 122590-92-5 1,1-difluoro-3,3-dimethyl-1-(phenylsulfonyl)butan-2-ol 
• 122590-91-4 1,1-difluoro-3-methyl-1-(phenylsulfonyl)butan-2-ol 
• 186963-82-6 1-{(2R,4R,5R)-4-(Benzenesulfonyl-difluoro-methyl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione 
• 122590-86-7 2,2-difluoro-1-phenyl-2-(phenylsulfonyl)ethan-1-ol 

Relevant academic research and scientific papers

α-(Difluoromethyl)styrene: Improved approach to grams scale synthesis

Improved, efficient, grams scale synthesis of α-(difluoromethyl)styrene (DFMST) based on nucleophilic difluoromethylation process using difluoromethylphenyl sulfone, is presented. Difluoromethylating agent (PhSO2CF2H) was obtained in two-step synthetic sequence with 69% overall yield. Three-step DFMST synthetic route was easily implemented for the preparation of gram quantities of the monomer, allowing for polymerization studies. The syntheses were based on the use of commercially available and reasonable in price starting materials and reagents.

C-H Electrophilic (phenylsulfonyl)difluoromethylation of (hetero)arenes with a newly designed reagent

The synthesis of an original electrophilic difluoromethylating reagent was successfully achieved upon a straightforward protocol (3 steps). Like a Swiss army knife, this bench-stable reagent allowed the functionalization of various classes of compounds under mild and transition metal-free conditions. Hence, an efficient and operationally simple tool for the construction of C(sp2)-, C(sp3)- and S-CF2SO2Ph bonds was provided, expanding the chemical space of PhSO2CF2-containing molecules. Late-stage functionalization of bioactive molecules and the synthesis of PhSO2CF2- and HCF2-analogs of Lidocaine were also successfully achieved.

Regio- and chemoselectivity in S- and O- difluoromethylation reactions using diethyl (bromodifluoromethyl)phosphonate

The effective difluoromethylations of various S- and O- based- nucleophiles, presenting a wide range of pKa values, using diethyl(bromodifluoromethyl) phosphonate (1) under basic conditions is described. These reactions, which rely on the quantitative generation of difluorocarbene formed through the hydrolysis of 1, were found to be effective only once the starting materials had pKa values of less than ca. 11. Importantly, in cases in which the substrates held two or three nucleophilic centers this feature was successfully implemented to achieve a high chemo- or regioselective difluoromethylation of the center exhibiting the lowest pKa value and the highest polarizability.

Method for constructing fluorine-containing methyl sulfone compound through multi-component coupling

The invention discloses a fluorine-containing methyl sulfone compound as shown in a formula (1) and a synthesis method thereof. Aromatic iodide (aryl iodide or heteroaryl iodide), an inorganic sulfur reagent and a fluorine-containing building block are used as reaction raw materials and react in a solvent under the action of alkali, a catalyst and an additive to obtain a series of fluorine-containing methyl sulfone compounds. According to the invention, the fluorine-containing sulfone compound is constructed by a one-pot two-step method by taking an inorganic sulfur reagent as a sulfur source under a catalytic condition, so that the defects of the traditional synthesis of a fluorine-containing sulfone compound by thioether oxidation are avoided. According to the synthesis strategy developed by the invention, some clinical methyl sulfone drugs can be modified, and monofluoro, difluoro and trifluoromethyl sulfone compounds can be successfully obtained, which have huge potential in the field of drug development in the future.

Preparation method of difluoromethyl sulfone compound

The invention discloses a preparation method of a difluoromethyl sulfone compound. The invention provides a preparation method of a difluoromethyl sulfone compound, which comprises the following step:in a solvent, in the presence of alkali and a phase transfer catalyst, carrying out difluoromethylation reaction shown in the specification on sulfinic acid and/or salt thereof and CHClF2 to obtain the difluoromethyl sulfone compound. The solvent is a mixed solvent of water and an organic solvent; The sulfinic acid and/or salt thereof comprises positive ions and negative ions, and the negative ions contain structural fragments shown as a formula I; and the difluoromethyl sulfone compound contains a structural fragment as shown in a formula II which is described in the specification. The preparation method provided by the invention has the advantages of accessible raw materials, wide substrate range, mild reaction conditions and simple operation, can implement separation without column chromatography, and is suitable for industrial production. The difluoromethyl sulfone compound can be obtained at a high yield.

Nucleophilic (Phenylsulfonyl/arylthio)difluoromethylation of Aldehydes with TMSCF2Br: A Three-Component Strategy

An efficient method for nucleophilic (phenylsulfonyl/arylthio)difluoromethylation of aldehydes with TMSCF2Br was developed. The reaction proceeds through in situ generation of difluorocarbene, which is captured by PhSO2Na or ArSNa to

Decarboxylative difluoromethylation of aldehydes with PhSO2CF2COOK: A facile and efficient access to difluoromethylated carbinols

A novel decarboxylative difluoromethylation reaction of PhSO2CF2COOK with aldehydes under metal- and ligand-free conditions has been developed. The reaction is very mild and tolerates a wide range of aldehydes (both enolizable and non-enolizable aldehydes), providing a facile and efficient method for the synthesis of structurally diverse difluoromethylated carbinols in moderate to excellent yields.

Copper-Mediated Di- and Monofluoromethanesulfonylation of Arenediazonium Tetrafluoroborates: Probing the Fluorine Effect

A copper-mediated di- and monofluoromethanesulfonylation of arenediazonium tetrafluoroborates using di- and monofluoromethanesulfinate reagents provides aryl difluoromethyl (or monofluoromethyl) sulfones in good yields. It was found that the relative reactivity of these sodium fluoroalkanesulfinates in the present reactions decreases in the following order: CH2FSO2Na > CF2HSO2Na > CF3SO2Na.

Conversion of methyl ketones and methyl sulfones into α-deutero-α,α-difluoromethyl ketones and α-deutero-α,α-difluoromethyl sulfones in three synthetic steps

Deuterodifluoromethyl ketones and sulfones were assembled in three synthetic steps from methyl ketones and sulfones, respectively. The key synthetic transformation is the deuteration of the difluorocarbanion generated by the release of trifluoroacetate from highly α-fluorinated gem-diols. High levels of deuterium on the “CF2D” group were routinely observed. This strategy is mild and versatile and it can be applied to both ketones and sulfones without additional concerns of over- or under-fluorination. Additional examples address issues of over-deuteration when compounds with other acidic protons are subjected to the reaction conditions. This process not only demonstrates a new method to install a “CF2D” group but also extends the scope of trifluoroacetate release to sulfones.

Radical (Phenylsulfonyl)difluoromethylation of Isocyanides with PhSO2CF2H under Transition-Metal-Free Conditions

An atom-economical method for radical (phenylsulfonyl)difluoromethylation of isocyanides with PhSO2CF2H under transition-metal-free conditions has been developed. A PhSO2CF2 radical is generated through the oxidation of PhSO2CF2- after the deprotonation of PhSO2CF2H in one pot. The reaction exhibits excellent functional-group tolerance and the resulting products can be further modified with the removal of a PhSO2 group to give other CF2-containing compounds.