80-00-2

Usage

Uses

Used in Pharmaceutical Industry:
Sulfenone is used as an impurity in Dapson (D193250) for the treatment of dermatitis herpetiformis, a chronic skin condition characterized by itchy blisters.
Used in Pest Control:
Sulfenone is used as an acaricide, which is a chemical agent designed to control or kill mites and ticks, helping to prevent infestations and the spread of diseases they may carry.
Used in Chemical Synthesis:
4-Chlorophenyl Phenyl Sulfone, an impurity of Dapson (D193250), is used in the synthesis of various chemical compounds, contributing to the development of new pharmaceuticals and other industrial applications.

InChI:InChI=1/C12H9ClO2S/c13-10-6-8-12(9-7-10)16(14,15)11-4-2-1-3-5-11/h1-9H

Upstream product

• 13343-26-5 phenyl p-chlorophenyl sulfide 
• 15481-45-5 methyl p-chlorobenzenesulphonate 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 71-43-2 benzene 
• 108-90-7 chlorobenzene 
• 98-09-9 benzenesulfonyl chloride 
• 98-11-3 benzenesulfonic acid 
• 80-18-2 Methyl benzenesulfonate 
• 98-66-8 4-chloro-benzenesulfonic acid 
• 14064-15-4 (4-chlorophenyl)trimethylstannane 
• 7446-70-0 aluminium trichloride 
• 7697-37-2 nitric acid 
• 80-07-9 4,4'-dichlorodiphenyl sulphone 
• 14752-66-0 sodium p-chlorobenzenesulphinate 

Downstream Products

• 38040-20-9 (4-chloro-3-nitro-phenyl)-(3-nitro-phenyl)-sulfone 
• 7402-69-9 p-hydroxyphenyl p-tolyl sulfone 
• 83627-59-2 3-(4-chlorophenylsulfonyl)-1-nitrobenzene 
• 139225-65-3 4'-Phenylsulfonyl-3,5-di-tert-butyl-<1,1'-biphenyl>-4-ol 
• 138453-04-0 3-(4-Benzenesulfonyl-phenyl)-2,5-dimethyl-1H-pyrrole 
• 28276-07-5 Bis(benzene-4-sulfonylphenyl)ether 
• 114194-15-9 (4-carboxyanilino)phenyl phenylsulfone 
• 100711-28-2 2-(4-benzenesulfonyl-phenoxy)-ethylamine 
• 1230-51-9 4-(phenylsulfonyl)biphenyl 
• 134983-66-7 C₃₀H₂₂O₈S₄ 
• 70714-83-9 4-hydrazinodiphenylsulfone 
• 90139-53-0 1,1'-(1-methylethylidene)bis[4-[4-(phenylsulfonyl)phenoxy]benzene] 
• 127-63-9 diphenyl sulphone 
• 35181-66-9 4-benzenesulfonylbenzenethiol 

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

Metal-free sulfonylation of arenes with: N -fluorobenzenesulfonimide via cleavage of S-N bonds: expeditious synthesis of diarylsulfones

A novel metal-free sulfonylation of arenes with N-fluorobenzenesulfonimide (NFSI) toward the synthesis of diarylsulfones has been developed. The reaction represents a rare example of sulfonylation reaction using NFSI as an efficient sulfonyl donor and the first example of acid-mediated sulfonylation of unactivated arenes with NFSI via selective cleavage of S-N bonds. This protocol provides a concise approach for the construction of pharmaceutically and biologically important diarylsulfones. Applications in the functionalization of natural products (e.g., β-estradiol) and in the synthesis of a key intermediate to an inhibitor of farnesyl-protein transferase, as well as in the gram-scale synthesis of the EPAC2 antagonist, are demonstrated. This journal is

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.

On the important transition of sugar-based surfactant as a microreactor for C-S coupling in water: From micelle to vesicle

A reversible, temperature-induced micelle-to-vesicle transition of a sugar-based pseudogemini surfactant (C11D12) was employed for copper-catalyzed C-S coupling in water. The phase behavior and morphology of the C11D12 aqueous solution were investigated by DLS and cryo-TEM. The aggregates undergo a series of transitions upon increasing the temperature: spherical micelles were initially transformed into large vesicles, but they eventually transformed into smaller vesicles. The vesicular catalytic protocol accommodates an excellent substrate scope with moderate to high yields. The mechanisms of temperature-induced aggregate transition and vesicular catalysis were elucidated by experimental results and DFT calculations. It was revealed that the charge layer of the vesicle grants stronger nucleophilicity to the PhSO2-Cu-D12Ga intermediate. Furthermore, the aqueous reaction medium can be recycled and reused several times after easily separating the precipitated product.

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.

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.

Pd/NHC-catalyzed arylsulfonylation of boronic acids: A general and direct protocol to access diarylsulfones

For the first time, robust NHC-Pd complexes have been demonstrated as highly efficient catalysts in the direct arylsulfonylation of boronic acids. Remarkably, a broad number of diaryliodonium salts as powerful electrophilic arylation reagents are well compatible to form functional ortho-substituted diarylsulfones in satisfactory yields. Owing to the stronger σ-donor and weaker π-acceptor properties, the acenaphthoimidazolylidene ligands exhibit higher catalytic activities towards this challenging one-step arylsulfonylation reaction.

Interfacing sugar-based surfactant micelles and Cu nanoparticles: A nanoreactor for C-S coupling reactions in water

A simple and sustainable synergistic catalytic protocol by interfacing nanomicelles and metal nanoparticles (MNPs) is reported for C-S coupling reactions in water. The sugar-based surfactant GluM was synthesized by introducing a PEG chain to stabilize MNPs and self-assembled to form nanomicelles. Cu2O nanoparticles were generated via in situ reduction of copper salt in an aqueous solution of the sugar-based surfactant. The nature of the interaction between nanomicelles and Cu2O nanoparticles was revealed by XPS, XRD, in situ IR, TEM, and 1H NMR. A broad substrate scope with moderate to excellent yields was documented and the recycling of the GluM/Cu aqueous mixture was surprising.

Selective oxidation of (hetero)sulfides with molecular oxygen under clean conditions

The development of eco-friendly and switchable catalytic systems for the conversion of a sole raw-material into distinct high-value products is a particularly attractive concept and a daunting synthetic challenge. In the present work, the first example of efficient and selective oxidation of sulfides to sulfones and sulfoxides using molecular oxygen under clean conditions was established.

Oxidation of aromatic sulfides with molecular oxygen: Controllable synthesis of sulfoxides or sulfones

The recent development of selective oxidation of aromatic sulfides with molecular oxygen was highlighted. The sulfoxides and sulfones could be obtained by simply switching the reaction media, i.e., bis(2-butoxyethyl)ether (BBE) or poly(ethylene glycol)dimethyl ether (PEGDME). The application of the high-boiling-point polyether as an initiator and green media can eliminate the need of large quantities of additives and volatile solvents. This strategy represents an economic and eco-friendly method that could find potential applications.