5713-57-5

Usage

Molecular structure

Consists of a thiophene ring with a sulfonyl group and a 4-methylphenyl group attached to it.

Stability

The sulfonyl group imparts good stability to the compound.

Reactivity

The sulfonyl group enhances the reactivity of the compound.

Use as intermediate

It is used as an intermediate in the synthesis of pharmaceuticals and agrochemicals.

Specific properties

Its specific properties and applications make it an important building block in the production of various chemicals and materials.

InChI:InChI=1/C11H10O2S2/c1-9-4-6-10(7-5-9)15(12,13)11-3-2-8-14-11/h2-8H,1H3

Upstream product

• 6165-68-0 thiophene boronic acid 
• 98-59-9 p-toluenesulfonyl chloride 
• 188290-36-0 thiophene 
• 124066-73-5 tris(thiophenyl-2-yl)bismuth 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 3437-95-4 2-Iodothiophene 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 52260-00-1 2-thiophene sulfonyl hydrazine 
• 36651-88-4 N-(4-methylphenylazo)pyrrolidine 
• 1026668-29-0 bis(2-thiophenyl)iodonium tosylate 
• 96-43-5 2-thienyl chloride 
• 58042-63-0 2-(p-tolylsulfanyl)thiophene 
• 455-16-3 p-toluenesulfonyl fluoride 

Relevant academic research and scientific papers

Sulfonylation of Bismuth Reagents with Sulfinates or SO2through BiIII/BiV Intermediates

Studies to explore the catalytic activities of main-group elements are attractive. We report here our study of sulfonylation of bismuth reagents with sulfinates or SO2 surrogates. Under oxidative conditions, triarylbismuthines and sulfinates were transformed into diaryl sulfones. A transition-metal-like two-electron redox process at the Bi center was achieved in this reaction. Sulfur dioxide generated in situ can also replace sulfinates to deliver the corresponding symmetric diaryl sulfones. A rational mechanism for this reaction was also proposed that involves a Bi(III)-Bi(V) manifold.

Nano copper catalyzed synthesis of symmetrical/unsymmetrical sulfones from aryl/alkyl halides and p-toluenesulfonylmethylisocyanide: TosMIC as a tosyl source

A magnetically induced nano copper-catalyzed efficient and mild route for the synthesis of diaryl and alkyl/aryl sulfones from aryl/alkyl halides and tosylmethyl isocyanide (TosMIC) has been developed. A variety of aryl and alkyl sulfones have been obtained in very good to excellent yields. Sulfones containing molecules have medicinal relevance as they are known to possess various activities such as antifungal, anti-HIV, antitumor, and anticancer. Herein, a magnetically induced nano copper-catalyzed efficient and mild route for the synthesis of biaryl and alkyl/aryl sulfones from aryl/alkyl halides and tosylmethyl isocyanide (TosMIC) has been developed. A variety of aryl and alkyl sulfones have been obtained in very good to excellent yields. In this newly developed protocol TosMIC acts as sulfonyl source. The catalyst can magnetically be recovered and recycled five times without significant loss in activity.

A practical synthesis of aryl sulfones via cross-coupling of sulfonyl hydrazides with aryltriazenes using copper/ionic liquid combination

A new and efficient approach adopting copper-catalyzed cross-coupling of sulfonyl hydrazides with aryltriazenes has been developed to synthesize aryl sulfones using Br?nsted acidic ionic liquid as promoter under ambient conditions. The process employs stable and easy to handle reacting partners, and is endowed with broad substrate scope.

Copper-mediated sulfonylation of aryl iodides and bromides with arylsulfonyl hydrazides in PEG-400

Sulfonylation using stable and readily available arylsulfonyl hydrazides and aryl iodides or bromides mediated by cupric acetate has been achieved. Using polyethylene glycol (PEG-400) as an eco-friendly medium, the coupling reaction could afford a series of unsymmetrical diaryl sulfones in moderate to good yields without the presence of additional ligands and base.

Rapid transformation of sulfinate salts into sulfonates promoted by a hypervalent iodine(III) reagent

An alternative method for forming sulfonates through hypervalent iodine(III) reagent-mediated oxidation of sodium sulfinates has been developed. This transformation involves trapping reactive sulfonium species using alcohols. With additional optimization of the reaction conditions, the method appears extendable to other nucleophiles such as electron-rich aromatic systems or cyclic ethers through a ring opening pathway.

A Metal-Free and Microwave-Assisted Efficient Synthesis of Diaryl Sulfones

An efficient and general protocol for the synthesis of diaryl sulfones via the metal-free coupling of readily available diaryliodonium salts and arenesulfinates in PEG-400 under microwave irradiation has been developed. Utilizing this metal-free and eco-friendly protocol, we have prepared various diaryl sulfones in high yields and shorter reaction times under mild conditions. Furthermore, the coupling of diaryliodonium with arenesulfinate salts with and without copper iodide provides a convenient access to various diaryl sulfones with high selectivity. Georg Thieme Verlag Stuttgart · New York.

A mild and efficient synthesis of aryl sulfones from aryl chlorides and sulfinic acid salts using microwave heating

The CuCl-catalyzed coupling of aryl chlorides and sulfinic acid salts provides a simple and extremely efficient route to unsymmetrical aryl sulfones in high to excellent yields under microwave irradiation within 3-30 minutes. Georg Thieme Verlag Stuttgart · New York.

Modifiable sulfur tethers as directing groups for aromatic C-H acetoxylation reactions

A designed new class of modifiable sulfur tethers for aromatic C-H bond functionalizations is presented. As a model, the palladium-catalyzed directed acetoxylation reaction was studied. The more challenging sulfoxide tethers were the most effective in this transformation, showing a broad functionality tolerance, high S oxido-redox stability and no catalyst poisoning. Preliminary mechanistic studies indicate that the higher reactivity and selectivity shown by the sulfoxide tethers vs. the corresponding sulfones can be attributed to an extra coordination of the sulfoxide S atom to the catalyst. The utility of the presented methodology to generate structurally interesting aromatic derivatives by a subsequent modification of the S-tether is also exemplified.

AMINOPYRIMIDINE COMPOUNDS AND METHODS OF USE

The invention relates to aminopyrimidine compounds useful for treating diseases mediated by polo-like kinase 1 (Plk1). The invention also relates to the therapeutic use of such aminopyrimidine compounds and compositions thereof in treating disease states associated with abnormal cell growth and unwanted cell proliferation.

Unsymmetrical diaryl sulfones through palladium-catalyzed coupling of aryl boronic acids and arylsulfonyl chlorides

A simple and efficient method for the synthesis of unsymmetrical diaryl sulfones using the palladium-catalyzed coupling of aryl boronic acids and arylsulfonyl chlorides has been developed. High product yields, a short reaction time, and mild reaction conditions are important features of this method.