28525-13-5

Usage

Uses

Used in Pharmaceutical Industry:
4-(phenylsulfonyl)benzonitrile is used as a building block for the synthesis of various pharmaceuticals due to its versatile chemical structure and potential pharmacological activities.
Used in Agrochemical Industry:
4-(phenylsulfonyl)benzonitrile is utilized as a precursor in the development of agrochemicals, contributing to the creation of effective products for agricultural applications.
Used in Dye and Pigment Industry:
4-(phenylsulfonyl)benzonitrile is employed as a component in the production of dyes and pigments, taking advantage of its chemical properties to enhance color characteristics.
Used in Material Science:
It serves as a key intermediate in the synthesis of functional materials, where its unique structure contributes to the development of advanced materials with specific properties.
Used in Medicinal Chemistry Research:
4-(phenylsulfonyl)benzonitrile is used as a research compound for exploring its potential role in treating certain diseases and conditions, highlighting its importance in the advancement of medical treatments.

Upstream product

• 98-10-2 benzenesulfonamide 
• 5361-54-6 4-(phenylsulfonyl)benzoic acid 
• 55204-60-9 4-benzenesulfonyl-benzoic acid amide 
• 623-00-7 4-bromobenzenecarbonitrile 
• 873-55-2 sodium benzenesulfonate 
• 3058-39-7 4-iodobenzonitrile 
• 98-80-6 phenylboronic acid 
• 98-09-9 benzenesulfonyl chloride 
• 2252-32-6 4-cyanophenyldiazonium tetrafluoroborate 
• 780-69-8 triethoxyphenylsilane 
• 17672-27-4 4-hydrazinobenzonitrile 
• 591-50-4 iodobenzene 
• 66003-76-7 Diphenyliodonium triflate 
• 824-79-3 sodium 4-methylbenzenesulfinate 

Downstream Products

• 5585-14-8 3,4-diphenyl-furazan 2-oxide 
• 111797-44-5 5-(4-benzenesulfonyl-phenyl)-3-phenyl-[1,2,4]oxadiazole 
• 65085-83-8 4'-(phenylsulfonyl)acetophenone 
• 4779-37-7 2-bromo-1-(4-(phenylsulfonyl)phenyl)ethan-1-one 
• 78064-96-7 4-(pyrrolidin-1-ylmethyl)benzonitrile 
• 928649-05-2 [(4-cyanophenyl)methyl](methyl)(isopropyl)amine 
• 1440419-03-3 tert-butyl 2-(4-cyanophenyl)pyrrolidine-1-carboxylate 
• 1588517-27-4 tert-butyl 2-(4-(phenylsulfonyl)phenyl)pyrrolidine-1-carboxylate 
• 1520089-89-7 tert-butyldimethyl(phenyl(4-(phenylsulfonyl)phenyl)methoxy)silane 
• 1454285-13-2 5-amino-N-[[4-(benzenesulfonyl)phenyl]methyl]furo[2,3-c]pyridine-2-carboxamide 
• 1454285-49-4 N-[[4-(benzenesulfonyl)phenyl]methyl]-5-[(diphenylmethylidene)amino]furo[2.3-c]pyridine-2-carboxamide 
• 1454285-48-3 N-[[4-(benzenesulfonyl)phenyl]methyl]-5-chlorofuro[2,3-c]pyridine-2-carboxamide 
• 1454285-18-7 4-amino-N-[[4-(benzenesulfonyl)phenyl]methyl]-1,3-dihydropyrrolo[3.4-c]pyridine-2-carboxamide 
• 1454285-00-7 7-amino-N-[[4-(benzenesulfonyl)phenyl]methyl]furo[2.3-c]pyridine-2-carboxamide 

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.

Method for synthesizing sulfone compounds under photocatalysis condition

The invention belongs to the technical field of compound preparation, and particularly relates to a method for synthesizing sulfone compounds under a photocatalysis condition. Aromatic hydrazine and sulfinate are used as raw materials, and under the action of alkali and a solvent, a sulfone compound is generated through reaction under the condition of air or oxygen under the illumination of visible light. According to the method disclosed by the invention, aryl hydrazine is used as an arylation reagent, polyacid salt is used as a catalyst or an organic photosensitizer is used as a catalyst, and the sulfones compound can be efficiently synthesized by coupling with sulfinate under the condition of room temperature through visible light irradiation. The method has good substrate universalityand relatively mild reaction conditions, is not only a substitute for synthesizing sulfone compounds by coupling from simple substrates reported at present, but also broadens the new application of the polyacid salt in the field of photocatalysis.

Sulfonylation of Aryl Halides by Visible Light/Copper Catalysis

An efficient visible-light-assisted, copper-catalyzed sulfonylation of aryl halides with sulfinates is reported. In our protocol, a single ligand CuI photocatalyst formed in situ was used in the photocatalytic transformation. Diverse organosulfones were obtained in moderate to good yields. This strategy demonstrates a promising approach toward the synthesis of diverse and useful organosulfones.

Metal-Free Aminomethylation of Aromatic Sulfones Promoted by Eosin Y

A metal-free α-aminomethylation of heteroaryls promoted by eosin Y under green light irradiation is reported. A large variety of α-trimethylsilylamines as precursor of α-aminomethyl radical species were engaged to functionalize sulfonyl-heteroaryls following a Homolytic Aromatic Substitution (HAS) pathway. This method has provided a range of α-aminoheteroaryl compounds including a functionalized natural product. The mechanism of this late-stage functionalization of aryls was investigated and suggests the formation of a sulfonyl radical intermediate over a reductive quenching cycle.

Ceramic boron carbonitrides for unlocking organic halides with visible light

Photochemistry provides a sustainable pathway for organic transformations by inducing radical intermediates from substrates through electron transfer process. However, progress is limited by heterogeneous photocatalysts that are required to be efficient, stable, and inexpensive for long-term operation with easy recyclability and product separation. Here, we report that boron carbonitride (BCN) ceramics are such a system and can reduce organic halides, including (het)aryl and alkyl halides, with visible light irradiation. Cross-coupling of halides to afford new C-H, C-C, and C-S bonds can proceed at ambient reaction conditions. Hydrogen, (het)aryl, and sulfonyl groups were introduced into the arenes and heteroarenes at the designed positions by means of mesolytic C-X (carbon-halogen) bond cleavage in the absence of any metal-based catalysts or ligands. BCN can be used not only for half reactions, like reduction reactions with a sacrificial agent, but also redox reactions through oxidative and reductive interfacial electron transfer. The BCN photocatalyst shows tolerance to different substituents and conserved activity after five recycles. The apparent metal-free system opens new opportunities for a wide range of organic catalysts using light energy and sustainable materials, which are metal-free, inexpensive and stable. This journal is

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.

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.

Organic photoredox catalysis enabled cross-coupling of arenediazonium and sulfinate salts: Synthesis of (un)symmetrical diaryl/alkyl aryl sulfones

We disclose herein the first transition-metal-and external oxidant/reductant-free visible-light-mediated synthesis of (un)symmetrical diaryl/alkyl aryl sulfones from arenediazonium tetrafluoroborates and sodium sulfinates using eosin Y as an organic photoredox catalyst. The utilization of visible light as an inexpensive and ecosustainable energy source, operational simplicity, ambient temperature and clean reaction in aqueous acetonitrile are the salient features of the developed protocol. The desired sulfones were also synthesized via a one-pot, two-step process directly from anilines and sulfinate salts in good to excellent yields.