22407-40-5

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2-Benzene sulfonylethiophene is utilized as an intermediate in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides. Its unique chemical structure allows for the creation of compounds with specific therapeutic or pesticidal properties.
Used in Organic Electronics and Optoelectronics:
Due to its strong electron-accepting properties, 2-benzenesulfonylethiophene is employed in the field of organic electronics and optoelectronics. It serves as a key component in the design and fabrication of electronic devices and optoelectronic systems, such as organic solar cells, organic light-emitting diodes (OLEDs), and organic field-effect transistors (OFETs).
Used in Dye and Pigment Production:
2-Benzene sulfonylethiophene is also used in the production of dyes and pigments, where its chemical properties enable the creation of vibrant and stable colorants for various applications, including textiles, plastics, and printing inks.
Used in Specialty Chemicals:
The versatility of 2-benzenesulfonylethiophene extends to its use in the production of specialty chemicals, where it is incorporated into formulations to enhance performance characteristics such as stability, reactivity, or solubility in specific applications.

InChI:InChI=1/C10H8O2S2/c11-14(12,10-7-4-8-13-10)9-5-2-1-3-6-9/h1-8H

Upstream product

• 16718-12-0 2-(Phenylthio)thiophene 
• 16629-19-9 thiophene-2-sulfonyl chloride 
• 71-43-2 benzene 
• 3437-95-4 2-Iodothiophene 
• 6165-68-0 thiophene boronic acid 
• 98-09-9 benzenesulfonyl chloride 
• 873-55-2 sodium benzenesulfonate 
• 1003-09-4 2-bromothiophene 
• 96-43-5 2-thienyl chloride 
• 1286747-84-9 2-thiophenesulfinic acid sodium salt 
• 66003-76-7 Diphenyliodonium triflate 
• 136768-52-0 lithium thiophene-2-sulfinate 
• 188290-36-0 thiophene 
• 98-80-6 phenylboronic acid 

Downstream Products

• 5324-78-7 5-benzenesulfonyl-thiophene-2-carboxylic acid 
• 98010-06-1 2-phenylsulfonyl-3-thiophenecarboxylic acid 
• 128839-71-4 2,3'-bisformylphenyl-2'-thienyl sulfone 
• 5324-81-2 phenyl 5-methyl-2-thienyl sulfone 
• 1313758-67-6 4-(5-benzenesulfonylthiophene-2-yl)benzonitrile 
• 1313758-68-7 methyl 4-(5-benzenesulfonylthiophene-2-yl)benzoate 
• 1313758-66-5 4-(5-benzenesulfonylthiophene-2-yl)benzaldehyde 

Relevant academic research and scientific papers

Visible-Light-Mediated Late-Stage Sulfonylation of Boronic Acids via N-S Bond Activation of Sulfonamides

A visible-light-mediated late-stage arylation of N-S bonds in sulfonamides has been developed with using readily available imines as sulfonyl radical source. Diverse complex sulfones could be synthesized by prefunctionalizaiton and subsequent N-S bond ary

A Copper(I)-Catalyzed Sulfonylative Hiyama Cross-Coupling

An air-tolerant Cu-catalyzed sulfonylative Hiyama cross-coupling reaction enabling the formation of diaryl sulfones is described. Starting from aryl silanes, DABSO and aryliodides, the reaction tolerates a large variety of polar functional groups (amines, ketones, esters, aldehydes). Control experiments coupled with DFT calculations shed light on the mechanism, characterized by the formation of a Cu(I)-sulfinate intermediate via fast insertion of a SO2 molecule.

Synthesis of Sulfones and Sulfonyl Derivatives using Sodium (tert-butyldimethylsilyl)oxymethanesulfinate

The present invention relates to a method for manufacturing a sulfone and sulfonyl derivative compound using sodium (tert-butyldimethylsilyl)oxymethanesulfinate, which is a novel organic sulfin salt, wherein the novel organic sulfin salt has good stability, environmental friendliness and economy, and is easy to handle, and thus significantly reduces the amount of transition metal catalysts and the amount of organic sulfin salts used when introducing aryl or alkenyl. Also, alkylation, arylation, amination, and fluorination are all possible during secondary functionalization. Therefore, the present invention can be usefully used in preparation and mass production of various kinds of sulfones and derivatives thereof including asymmetric sulfone derivatives.

Hantzsch Ester as a Visible-Light Photoredox Catalyst for Transition-Metal-Free Coupling of Arylhalides and Arylsulfinates

Diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (HEH) has been utilized as a visible-light photoredox catalyst for the cross coupling of arylhalides and arylsulfinates without transition metal, sacrificial agent, and mediator. This method is compatible with various functional groups and provides diaryl sulfones in good to high yields. Mechanistic studies indicate that this reaction undergoes the stepwise light irradiation of HE?, single electron transfer (SET) in donor–acceptor complex (DAC) from *HE? to arylhalide, trapping of aryl radical with sulfinate, and SET oxidation of sulfone radical anion by HE. to sulfone by the DAC method.

Method for preparing heterocyclic sulfone organic compounds

The invention discloses a method for preparing heterocyclic sulfone organic compounds from heterocyclic aryl halogen and aryl sulfinate. The method comprises the following steps: 1, in an inert gas protection, according to the molar ratio of heterocyclic aryl halogen compounds, benzene sulfinate compound, inorganic alkali to HEH of 1:2:1.5:0.2, adding the reactants into a reaction container provided with a stirring device, then adding dimethyl sulfoxide, and carrying out stirring reaction for 24 hours at room temperature under blue LED irradiation, so as to obtain the heterocyclic sulfone organic compound. According to the invention, HEH is used as a catalyst for the first time under the condition of not adding any auxiliary transition metal catalyst and precious metal photosensitizer, anda series of cross-coupling reactions of heterocyclic aryl halogen and benzene sulfinate are realized. In addition, the whole process is green, efficient and easy to operate, and the method is excellent for synthesizing the heterocyclic sulfone organic compound.

Silyloxymethanesulfinate as a sulfoxylate equivalent for the modular synthesis of sulfones and sulfonyl derivatives

An efficient protocol for the modular synthesis of sulfones and sulfonyl derivatives has been developed utilizing sodium tert-butyldimethylsilyloxymethanesulfinate (TBSOMS-Na) as a sulfoxylate (SO22-) equivalent. TBSOMS-Na, easily prepared from the commercial reagents Rongalite and TBSCl, serves as a potent nucleophile in S-alkylation and Cu-catalyzed S-arylation reactions with alkyl and aryl electrophiles. The sulfone products thus obtained can undergo the second bond formation at the sulfur center with various electrophiles without a separate unmasking step to afford sulfones and sulfonyl derivatives such as sulfonamides and sulfonyl fluorides.

Regiospecific Cleavage of S-N Bonds in Sulfonyl Azides: Sulfonyl Donors

Sulfonyl azides have been widely used as sulfonamido, diazo, and azido donors, as well as all-nitrogen 1,3-dipoles donors in synthetic chemistry. Here, the sulfonyl azides were used as efficient sulfonyl donors, which is very unusual. Trifluoromethanesulfonic acid-induced formation of the sulfonyl cation reactive species from sulfonyl azides was developed and used for the first time to couple various inactivated arenes to prepare sulfones at ambient temperature.

A Class of Amide Ligands Enable Cu-Catalyzed Coupling of (Hetero)aryl Halides with Sulfinic Acid Salts under Mild Conditions

The amide derived from 4-hydroxy-l-proline and 2,6-dimethylaniline is a powerful ligand for Cu-catalyzed coupling of (hetero)aryl halides with sulfinic acid salts, allowing the formation of a wide range of (hetero)aryl sulfones from the corresponding (hetero)aryl halides at considerably low catalytic loadings. The coupling of (hetero)aryl iodides and sodium methanesulfinate proceeds at room temperature with only 0.5 mol % CuI and ligand, representing the first example for Cu-catalyzed arylation at both low catalytic loading and room temperature.

Visible-Light Photoredox/Nickel Dual Catalysis for the Cross-Coupling of Sulfinic Acid Salts with Aryl Iodides

An efficient cross-coupling of sodium or lithium sulfinates with aryl iodides, using a combination of nickel and photoredox catalysis, is described. The dual catalyst system enables a versatile synthesis of aryl sulfones at room temperature in good yields and displays a broad functional group compatibility. The potential utility of this method in the late-stage diversification of complex molecules and in the conversion of organolithium reagents and sulfur dioxide into sulfones is demonstrated.

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.