31377-97-6

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
1-(4-bromophenyl)-2-[(4-methylphenyl)sulfonyl]ethanone is used as a reagent in the synthesis of pharmaceuticals and agrochemicals. Its unique chemical structure allows it to be a key component in the production of various organic compounds.
Used in Organic Synthesis:
1-(4-bromophenyl)-2-[(4-methylphenyl)sulfonyl]ethanone is also utilized in organic synthesis, where it contributes to the creation of a wide range of organic compounds that have different applications across various industries.
Used in Medicinal Chemistry and Drug Discovery:
Due to its pharmacological activities, 1-(4-bromophenyl)-2-[(4-methylphenyl)sulfonyl]ethanone has potential applications in the fields of medicinal chemistry and drug discovery. Its properties make it a promising candidate for the development of new drugs and therapies.
Overall, 1-(4-bromophenyl)-2-[(4-methylphenyl)sulfonyl]ethanone is a versatile and important chemical compound with various industrial and research applications, making it a valuable asset in the fields of pharmaceuticals, agrochemicals, and organic synthesis.

Upstream product

• 342808-62-2 1-(4-bromophenyl)vinyl acetate 
• 98-59-9 p-toluenesulfonyl chloride 
• 657-84-1 sodium tosylate 
• 99-90-1 para-bromoacetophenone 
• 70-55-3 toluene-4-sulfonamide 
• 117465-34-6 2-bromo-1-(4-bromophenyl)ethanol 
• 99-73-0 para-bromophenacyl bromide 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 89108-50-9 1-(1-azidovinyl)-4-bromobenzene 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 536-57-2 p-toluene sulfinic acid 
• 5391-88-8 1-(4-bromophenyl)ethanol 

Downstream Products

• 31378-03-7 1-phenyl-2-tosylethanone 
• 99-90-1 para-bromoacetophenone 
• 1610556-10-9 4-(3-acetyl-5-(4-bromophenyl)-4-tosyl-1H-pyrazol-1-yl)benzenesulfonamide 
• 68275-75-2 4-(4-bromo-phenyl)-5-(toluene-4-sulfonyl)-[1,2,3]selenadiazole 
• 103-19-5 di(p-tolyl) disulfide 

Relevant academic research and scientific papers

Acridine Orange Hemi(Zinc Chloride) Salt as a Lewis Acid-Photoredox Hybrid Catalyst for the Generation of α-Carbonyl Radicals

A readily accessible organic-inorganic hybrid catalyst is reported for the reductive fragmentation of α-halocarbonyl compounds. The robust hybrid catalyst is a self-stabilizing combination of ZnCl2 Lewis acid and acridine orange as the photoactive organic dye. Mechanistic specifics of this hybrid catalyst have been studied in detail using both photophysical and electrochemical experiments. A systematic study enabled the discovery of the appropriate Lewis acid for the effective LUMO stabilization of α-halocarbonyl compounds and thereby lowering of reduction potential within the range of a standard organic dye. This strategy resolves the issues like dehalogenative hydrogenation or homo-coupling of alkyl radicals by guiding the photoredox cycle through an oxidative quenching pathway. The cooperativity between the photoactive organic dye and the Lewis acid counterparts empowers functionalization with a wide range of coupling partners through efficient and controlled generation of alkyl radicals and serves as an appropriate alternative to the expensive late transition metal-based photocatalysts. To demonstrate the application potential of this cooperative catalytic system, four different synthetic transformations of α-carbonyl bromides were explored with broad substrate scopes.

Copper-Catalyzed Aerobic Oxidative Cleavage of Unstrained Carbon-Carbon Bonds of 1,1-Disubstituted Alkenes with Sulfonyl Hydrazides

Alkoxy radical-mediated carbon-carbon bond cleavages have emerged as a powerful strategy to complement traditional ionic-type transformations. However, carbon-carbon cleavage reaction triggered by alkoxy radical intermediate derived from the combination of alkyl radical and dioxygen, is scarce and underdeveloped. Herein, we report alkoxy radical, which was generated from alkyl radical and dioxygen, mediated selective cleavage of unstrained carbon-carbon bond for the oxysulfonylation of 1,1-disubstituted alkenes, providing facile access to a variety of valuable β-keto sulfones. Mechanistic experiments indicated alkoxy radical intermediate that underwent subsequent regioselective β-scission might be involved in the reaction and preliminary computational studies were conducted to provide a detailed explanation on the regioselectivity of the C—C bond cleavage. Notably, the strategy was successfully applied for constructing uneasily obtained architecturally intriguing molecules.

Photosensitizer-free synthesis of β-keto sulfones: Via visible-light-induced oxysulfonylation of alkenes with sulfonic acids

A practical and environment-friendly methodology for the construction of β-keto sulfones through visible-light induced direct oxysulfonylation of alkenes with sulfonic acids at ambient temperature under open-air conditions was developed. Most importantly, the reaction proceeded smoothly without the addition of any photocatalyst or strong oxidant, ultimately minimizing the production of chemical waste.

Oxy-sulfonylation of terminal alkynesviaC-S coupling enabled by copper photoredox catalysis

We report the first literature example using visible light-induced trimethylsilyl azide (TMS-N3)-assisted copper-catalyzed oxy-sulfonylation of terminal C-C bonds to form β-keto sulfones (C-S bond formation). TMS-N3promotes the reaction by facilitating the formation of sulfonyl radicals, which later decompose into N2gas upon light irradiation. This method involves the use of commercially available and stable starting materials. Also, a wide range of functional groups have been well-tolerated under the current photoredox process, evading the side product formation. Potent biologically active compounds, such as CES1, 11β-HSD1 inhibitors, anti-analgesic agents, and reactive synthesis intermediates were synthesized to demonstrate the synthetic utility of the current methodology. Moreover, green chemistry metrics and Eco-scale evaluation for the current photochemical method show that the protocol is eco-friendly and highly efficient.

Cu(OTf)2-Catalyzed efficient sulfonylation of vinyl azides with sodium sulfinates

A simple oxidative cross-coupling reaction between vinyl azides and sodium sulfinates was developed. This reaction uses commercial arylsulfinates that are more efficient, cheaper, and more stable as sulfonylation reagents, for efficiently, cheaply, and environmentally friendly synthesis of β-keto sulfones. And the reaction has the advantages of simple operation, high efficiency, good yield, and also has a wide range of functional group tolerance.

Electrochemical Synthesis of β-Ketosulfones from Switchable Starting Materials

A synthesis of β-ketosulfones via sulfination of aryl methyl ketones and aryl acetylenes with sodium sulfinates under mild electrochemical conditions, in moderate to good chemical yields, is described. In particular, an electrochemical sulfination reaction of alkynes with sulfinate salts has never been explored. An environmentally friendly characteristic of this reaction is that it uses electricity as a valuable energy source for electrochemical synthesis of β-ketosulfones. This strategy is more convenient and practical compared to previous approaches.

Preparation method of beta-carbonyl sulfone compound

The invention discloses a preparation method of a beta-carbonyl sulfone compound, and belongs to the technical field of organic synthesis. The preparation method of the beta-carbonyl sulfone compoundis provided for solving the problems that in the prior art, operation is complex, the substrate range is narrow, and the functional group tolerance is poor. The preparation method comprises the stepsof taking a compound shown in formula I and a compound shown in formula II as raw materials, taking copper salt as a catalyst, carrying out reaction in an organic solvent, and after the reaction is completed, carrying out aftertreatment to obtain the beta-carbonyl sulfone compound. The preparation method is simple and convenient to operate, mild in reaction condition, wide in substrate range and good in functional group tolerance, the yield reaches up to 93%, and the synthesis cost is remarkably reduced.

Sulfated tungstate/dioxygen: A new catalytic system for oxysulfonylation of styrenes to form β-keto sulfones

A new system for synthesis of a wide range of β-keto sulfones using sulfated tungstate as a heterogeneous catalyst and oxygen as an environmentally benign oxidant with aryl hydrazides and styrenes as reacting counterparts has been developed. The preliminary experimental results support the involvement of free radical species. Thus, aryl sulfonyl free radicals, generated by oxidation of aryl sulfonyl hydrazides, subsequently undergo a tandem addition to styrenes to form intermediate benzyl free radicals, and oxygen capture and oxidation to furnish β-keto sulfones. The method is mild and efficient with easy workup procedures. The catalyst is recyclable. This journal is

Metal-Free Electrochemical Coupling of Vinyl Azides: Synthesis of Phenanthridines and β-Ketosulfones

We reported an efficient and environmentally benign electrochemical synthesis of phenanthridines by oxidative coupling of vinyl azides with sodium azide or benzenesulfonyl hydrazides, for the first time. The reaction conditions are mild, and no additional metal-catalyst or exogenous oxidants are needed. The protocol has broad substrate scope and high functional group tolerance. Furthermore, this green electrochemical procedure can be readily extended to the synthesis of β-ketosulfones. Gram scale reactions further demonstrate the practicability.

Visible light promoted sulfonylation and sulfonylcarbonylation of alkenes

Visible light promoted sulfonylation and sulfonylcarbonylation reactions of readily available alkenes with TosMIC for the synthesis of valuable vinyl sulfones and β-keto sulfones were described. A reasonable radical involved mechanism is proposed.