61820-95-9

Usage

Uses

Used in Photopolymerization Processes:
4'-METHYL-2(P-TOLYL SULFONYL)ACETOPHENONE is used as a photoinitiator for initiating photopolymerization processes. It forms a stable free radical, which is crucial for the polymerization of certain materials under exposure to light, facilitating the curing of coatings, adhesives, and other polymeric systems.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 4'-METHYL-2(P-TOLYL SULFONYL)ACETOPHENONE is utilized as a key intermediate. Its role in the synthesis of various pharmaceutical compounds is significant, contributing to the development of new drugs and active pharmaceutical ingredients.
Used in Organic Material Synthesis:
4'-METHYL-2(P-TOLYL SULFONYL)ACETOPHENONE is also employed in the synthesis of other organic materials, where its reactivity and properties are leveraged to create a range of chemical products, from specialty chemicals to advanced materials for various applications.

InChI:InChI=1/C16H16O3S/c1-12-3-7-14(8-4-12)16(17)11-20(18,19)15-9-5-13(2)6-10-15/h3-10H,11H2,1-2H3

Upstream product

• 61737-10-8 1-(p-tolyl)-2-(p-tolylthio)ethan-1-one 
• 54731-27-0 1-p-methylphenyl-1-trimethylsiloxyethene 
• 98-59-9 p-toluenesulfonyl chloride 
• 766-97-2 4-n-methylphenylacetylene 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 122-00-9 para-methylacetophenone 
• 619-41-0 4-(bromoacetyl)toluene 
• 68819-94-3 p-tolyl benzeneselenosulfonate 
• 10486-08-5 sodium p-thiocresolate 
• 4209-24-9 p-methylphenacyl chloride 
• 1338239-09-0 1-butyl-3-methylimidazolium p-toluenesulfinate 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 40805-62-7 2-iodo-1-(4-methylphenyl)ethanone 
• 657-84-1 sodium tosylate 

Downstream Products

• 122772-73-0 (E)-1-Phenyl-3-pyridin-4-yl-2-(toluene-4-sulfonyl)-propenone 
• 122772-77-4 (E)-3-Pyridin-4-yl-2-(toluene-4-sulfonyl)-1-p-tolyl-propenone 
• 122772-78-5 (Z)-3-Thiophen-2-yl-2-(toluene-4-sulfonyl)-1-p-tolyl-propenone 
• 122772-76-3 (E)-3-(4-Chloro-phenyl)-2-(toluene-4-sulfonyl)-1-p-tolyl-propenone 
• 122772-74-1 1-Phenyl-2-(toluene-4-sulfonyl)-3-p-tolylpropenone 
• 122772-75-2 (E)-3-(2-Hydroxy-phenyl)-2-(toluene-4-sulfonyl)-1-p-tolyl-propenone 
• 37891-96-6 1-((iodom ethyl)sulfonyl)-4-methylbenzene 
• 206132-42-5 5-(toluene-4-sulfonyl)-4-p-tolyl-[1,2,3]selenadiazole 
• 5337-93-9 4'-methylpropiophenone 
• 2001-28-7 2-phenyl-1-p-tolyl-ethanone 
• 681125-53-1 2-diazo-2-(toluene-4-sulfonyl)-1-p-tolylethanone 

Relevant academic research and scientific papers

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.

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.

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.

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.

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.

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.

Building a Pyrazole–Benzothiadiazole–Pyrazole Photosensitizer into Metal–Organic Frameworks for Photocatalytic Aerobic Oxidation

Charge separation plays a crucial role in regulating photochemical properties and therefore warrants consideration in designing photocatalysts. Metal–organic frameworks (MOFs) are emerging as promising candidates for heterogeneous photocatalysis due to their structural designability and tunability of photon absorption. Herein, we report the design of a pyrazole–benzothiadiazole–pyrazole organic molecule bearing a donor–acceptor–donor conjugated π-system for fast charge separation. Further attempts to integrate such a photosensitizer into MOFs afford a more effective heterogeneous photocatalyst (JNU-204). Under visible-light irradiation, three aerobic oxidation reactions involving different oxygenation pathways were achieved on JNU-204. Recycling experiments were conducted to demonstrate the stability and reusability of JNU-204 as a robust heterogeneous photocatalyst. Furthermore, we illustrate its applications in the facile synthesis of pyrrolo[2,1-a]isoquinoline-containing heterocycles, core skeletons of a family of marine natural products. JNU-204 is an exemplary MOF platform with good photon absorption, suitable band gap, fast charge separation, and extraordinary chemical stability for proceeding with aerobic oxidation reactions under visible-light irradiation.

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.

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.