24437-48-7

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-CHLOROPHENYL)-2-(METHYLSULFONYL)ETHANONE is used as a chemical intermediate for the synthesis of various drugs. Its unique structure and properties make it a valuable component in the development of new pharmaceuticals, contributing to the advancement of medical treatments and therapies.
Used in Agrochemical Industry:
In the agrochemical sector, 1-(4-CHLOROPHENYL)-2-(METHYLSULFONYL)ETHANONE serves as a key intermediate in the production of agrochemicals. Its application in this industry aids in the development of effective and efficient solutions for agricultural challenges, such as pest control and crop protection.
Used in Research and Development:
1-(4-CHLOROPHENYL)-2-(METHYLSULFONYL)ETHANONE is utilized in research and development within the pharmaceutical industry. Its unique properties and reactivity make it an essential tool for scientists and researchers working on the discovery and optimization of new drug candidates and agrochemical products.

InChI:InChI=1/C9H9ClO3S/c1-14(12,13)6-9(11)7-2-4-8(10)5-3-7/h2-5H,6H2,1H3

Upstream product

• 20277-69-4 sodium methansulfinate 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 91193-23-6 O-ethyl S-2-(4-chlorophenyl)-2-oxoethyl carbonodithioate 
• 67-68-5 dimethyl sulfoxide 
• 1073-67-2 4-vinylbenzyl chloride 
• 873-73-4 4-n-chlorophenylacetylene 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 67-71-0 dimethylsulfone 
• 153784-07-7 ethyl 2-[2-(4-chlorophenyl)-2-oxoethyl]sulfonylacetate 
• 99-91-2 para-chloroacetophenone 
• 58518-76-6 ((1-(4-chlorophenyl)vinyl)oxy)trimethylsilane 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 1599463-31-6 (Z)-N-(1-(4-chlorophenyl)-2-(methylsulfonyl)vinyl)acetamide 
• 1599463-03-2 (S)-N-(1-(4-chlorophenyl)-2-(methylsulfonyl)ethyl)acetamide 
• 1599462-77-7 C₁₁H₁₂ClNO₃S 

Relevant academic research and scientific papers

Copper-catalyzed aerobic oxidative cross-coupling reactions of vinylarenes with sulfinate salts: A direct approach to β-ketosulfones

A copper-catalyzed aerobic oxidative cross-coupling reactions for the synthesis of β-ketosulfones via formation of a C[sbnd]S bond has been demonstrated. Promoted by the crucial copper catalyst, perfect selectivity and good to excellent yields could be achieved. This method, including inexpensive copper catalyst, wide functional group tolerance, and open air conditions, make it very attractive and practical. More importantly, it also provides a versatile tool for the construction of β-ketosulfones from basic starting materials under mild conditions.

Visible-light-promoted aerobic oxidative synthesis of β-ketosulfones under photocatalyst-free conditions

A simple and convenient visible-light-mediated method has been developed for the construction of β-ketosulfones via aerobic oxidative difunctionalization of alkynes with arylazo sulfones and dioxygen in air under photocatalyst-free conditions. The present photochemical methodology provides a facile and attractive protocol to construct a series of β-ketosulfones in moderate to good yields.

Synthesis of β-ketosulfone derivatives as new non-cytotoxic urease inhibitors in vitro

Background: Peptic ulcer and urolithiasis are largely due to infection caused by urease-producing bacteria. Therefore, the discovery of urease inhibitors is an important area of medicinal chemistry research. Objective: The main aim of the work was to identify novel urease inhibitors with no cytotoxicity. Method: During the current study, a series of β-ketosulfones 1-26 was synthesized in two steps and evaluated for their in vitro urease inhibition potential. Results: Out of twenty-six compounds, seventeen have shown good to significant urease inhibitory activity with IC50 values ranging between 49.93-351.46 μM, in comparison to standard thiourea (IC50 = 21 ± 0.11 μM). Moreover, all compounds found to be non-cytotoxic against normal 3T3 cell line. Conclusion: This study has identified β-ketosulfones as novel and non-cytotoxic urease inhibitors.

Preparation method of beta-carbonyl sulfone compound promoted by visible light

The invention discloses a preparation method of a beta-carbonyl sulfone compound promoted by visible light. The preparation method includes the following steps that olefin and aryl-sulphonazo are mixed with an organic solvent and water, and then a reaction is conducted for 16-24 hours at room temperature under visible illumination; and after the reaction, ethyl acetate is used for extracting reaction liquid, and the beta-carbonyl sulfone compound is obtained after concentration and column chromatography isolation of an extract. According to the method, clean light energy is used as reaction energy, oxygen in air is used as an oxidant and an oxygen source, the beta-carbonyl sulfone compound is effectively synthesized at the room temperature, the method does not require any photocatalyst orequivalent inorganic oxidant, and has the advantages of easy and convenient operation, low energy consumption, high reaction safety, environmental friendliness and the like.

Photocatalyst-Free Visible Light-Induced Synthesis of β-Oxo Sulfones via Oxysulfonylation of Alkenes with Arylazo Sulfones and Dioxygen in Air

A catalyst-free strategy has been established for the synthesis of β-oxo sulfones via visible light-induced oxysulfonylation of alkenes with arylazo sulfones with dioxygen in air. The present photoinduced transformation proceeds smoothly at room temperature in the absence of an external photosensitizer, which not only provides a mild and efficient approach to various β-oxo sulfones, but also opens a different reaction mode for the photochemical reaction of arylazo sulfones.

Efficient synthesis of chiral β-hydroxy sulfones: Via iridium-catalyzed hydrogenation

A highly efficient Ir/f-Amphol-catalyzed asymmetric hydrogenation of prochiral β-keto sulfones was successfully developed to prepare a series of chiral β-hydroxy sulfones with good to excellent results (62%->99% conversions, 35%-99% yields and 86%->99% ee). Our Ir/f-Amphol L4 catalytic system exhibited very high activity; the gram-scale asymmetric hydrogenation was performed well with just 0.005 mol% catalyst loading (S/C = 20,000) to afford the desired product 2a with >99% conversion, 99% yield and 93% ee.

Facile Synthesis of β-Keto Sulfones Employing Fenton's Reagent in DMSO

A new facile method for the synthesis of β-keto sulfones employing xanthates, DMSO, and Fenton's reagent is described. The reaction proceeds under very mild conditions providing a cost-effective straightforward approach to various β-keto sulfones in high yields.

Nickel-Catalyzed Highly Enantioselective Hydrogenation of β-Acetylamino Vinylsulfones: Access to Chiral β-Amido Sulfones

The nickel/(S)-Binapine complex was found to be an efficient catalyst for asymmetric hydrogenation of β-acetylamino vinylsulfones to afford chiral β-Amido sulfones with excellent yields and enantioselectivities (up to 95% yields and >99% ee). This protocol has good compatibility with a series of substituted (Z)-β-acetylamino vinylsulfones or Z/E isomeric mixtures. A gram-scale reaction has also been achieved in the presence of a 0.2 mol % catalyst loading.

CO/O2 assisted oxidative carbon-carbon and carbon-heteroatom bond cleavage for the synthesis of oxosulfonates from DMSO and olefins

Selective carbon-carbon and carbon-heteroatom bond cleavage was achieved in a one reaction system. With this strategy a novel Pd/Cu-catalyzed aerobic oxidative oxosulfonation of olefins with DMSO has been developed. Preliminary mechanistic investigations indicated that CO/O2 assisted the bond cleavage and the leaving groups from the starting materials were trapped by O2 and underwent a hydroxylation process.

Iron(III)-catalyzed aerobic oxidation and cleavage/formation of a C-S bond

A new iron(III)-catalyzed synthesis of β-oxo sulfones is described that employs vinylarenes and readily available dimethyl sulfoxide (DMSO) with hydrazine and oxygen as the oxidant. The reaction tolerates various functional group substituents on the vinylarene substrates to afford β-oxo sulfones in moderate to good yields. The cleavage and formation of the C-S bond are the key steps of this transformation.