34101-22-9

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
(E)-2-(4-chlorophenyl)ethenyl phenyl sulfone is used as a key building block for the synthesis of pharmaceuticals and agrochemicals. Its unique chemical structure allows for the development of new compounds with specific therapeutic or pesticidal properties, contributing to the advancement of these industries.
Used as a Cross-linking Agent in Polymerization Reactions:
In the field of polymer chemistry, (E)-2-(4-chlorophenyl)ethenyl phenyl sulfone is employed as a cross-linking agent. Its incorporation into polymerization reactions enhances the structural integrity and stability of the resulting polymers, leading to improved material properties and performance.
Used as a Fluorescent Imaging Agent in Biological Studies:
(E)-2-(4-chlorophenyl)ethenyl phenyl sulfone also finds application in biological research as a fluorescent imaging agent. Its ability to emit fluorescence under specific conditions makes it a valuable tool for visualizing and tracking biological processes at the molecular level, aiding in the understanding of complex biological systems.
Used as a Starting Material for the Synthesis of New Materials:
Furthermore, (E)-2-(4-chlorophenyl)ethenyl phenyl sulfone serves as a starting material for the synthesis of new materials with specialized properties. Its unique chemical structure can be modified and combined with other compounds to create novel materials with specific characteristics, such as enhanced thermal stability, improved mechanical properties, or unique optical properties.
It is crucial to handle (E)-2-(4-chlorophenyl)ethenyl phenyl sulfone with care, as it may pose health risks if ingested or inhaled and can cause skin and eye irritation. Proper safety measures should be taken during its use to minimize potential hazards.

Upstream product

• 3112-85-4 methylphenylsulfonate 
• 2788-86-5 4-Chlorostyrene oxide 
• 873-55-2 sodium benzenesulfonate 
• 1615-02-7 3-(4-chlorophenyl)prop-2-enoic acid 
• 1073-67-2 4-vinylbenzyl chloride 
• 3959-23-7 benzenesulfonylacetic acid 
• 104-88-1 4-chlorobenzaldehyde 
• 98-09-9 benzenesulfonyl chloride 
• 32291-83-1 1-(4'-chlorophenyl)-2-(phenylsulfanyl)ethene 
• 683-08-9 Diethyl methylphosphonate 
• 368-43-4 phenylsulfonyl fluoride 
• 5535-48-8 PVS 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 126613-18-1 1-(benzenesulfonyl)-2-(p-chlorophenyl)acetylene 

Downstream Products

• 66022-86-4 [2-Benzenesulfonyl-1-(4-chloro-phenyl)-ethyl]-dimethyl-amine 
• 911832-91-2 methyl 4-phenylsulfonyl-3-(4-chlorophenyl)butyrate 
• 89130-31-4 (Z)-1-chloro-4-(3-methylbut-1-en-1-yl)benzene 
• 911833-01-7 4-benzenesulfonyl-3-(4-chloro-phenyl)-2-cyano-butyric acid ethyl ester 
• 1245924-50-8 (2-[(2R,3S)-3-(4-chlorophenyl)-4-(phenylsulfonyl)butan-2-yl]phenyl)(p-tolyl)-(S)-sulfoxide 
• 1245924-63-3 [(2S,3R)-3-(2-((S)-p-tolylsulfinyl)phenyl)-4-phenyl-1-(phenylsulfonyl)butan-2-yl]-4-chlorobenzene 

Relevant academic research and scientific papers

Controlled Synthesis of β-Keto Sulfones and Vinyl Sulfones under Electrochemical Oxidation

Selective sulfonylation and oxosulfonylation of alkenes with sulfinates have been developed via anodic oxidation in an undivided cell. The novel electrosynthetic method provided β-keto sulfones and vinyl sulfones with good to excellent yields in the absence of any transition metal catalyst and oxidants. Mechanism studies show that two different pathways involved in these two transformations.

Generation of potent Nrf2 activators via tuning the electrophilicity and steric hindrance of vinyl sulfones for neuroprotection

Oxidative stress is constantly involved in the etiopathogenesis of an ever-widening range of neurodegenerative diseases. As a consequence, effective repression of cellular oxidative stress to a redox homeostatic condition is a promising and feasible strategy to treat, or at least retard the progression of, such disorders. Nrf2, a primary orchestrator of cellular antioxidant response machine, is responsible for detoxifying and compensating for deleterious oxidative stress via transcriptional activation of a diverse array of antioxidant biomolecules. In the framework of our persistent interest in disclosing small molecules that interfere with cellular redox-regulating machinery, we report herein the synthesis, optimization, and biological assessment of 47 vinyl sulfone scaffold-bearing small molecules, most of which exhibit robust neuroprotective effect against H2O2-mediated lesions to PC12 cells. After initial screening, the most potent neuroprotective compounds 9b and 9c with marginal cytotoxicity were selected for the follow-up studies. Our results demonstrate that their neuroprotective effects are attributed to the up-regulation of a panel of antioxidant genes and corresponding gene products. Further mechanistic studies indicate that Nrf2 is indispensable for the cellular performances of 9b and 9c, arising from the fact that silence of Nrf2 gene drastically nullifies their protective action. Taken together, 9b and 9c discovered in this work merit further development as neuroprotective candidates for the treatment of oxidative stress-mediated pathological conditions.

Visible-Light-Induced Three-Component Intermolecular Trifluoromethyl-Alkenylation Reactions of Unactivated Alkenes

Herein, we describe a practical protocol for efficient, mild, visible-light-induced three-component intermolecular trifluoromethyl-alkenylation reactions of unactivated alkenes. The protocol has good functional group tolerance and a broad substrate scope. Using this protocol, we not only introduced a trifluoromethyl group into alkenes but also converted unactivated alkenes to styrene-based activated alkenes, in addition to accomplishing late-stage functionalization of pharmaceutical intermediates. (Figure presented.).

Visible-Light-Mediated Alkenylation of Alkyl Boronic Acids without an External Lewis Base as an Activator

Herein we report a protocol for the direct visible-light-mediated alkenylation of alkyl boronic acids at room temperature without an external Lewis base as an activator, and we propose a mechanism involving benzenesulfinate activation of the alkyl boronic acids. The protocol permits the efficient functionalization of a broad range of cyclic and acyclic primary and secondary alkyl boronic acids with various alkenyl sulfones. We demonstrated its utility by preparing or functionalizing several pharmaceuticals and natural products.

Visible-light-mediated alkylation of 4-alkyl-1,4-dihydropyridines with alkenyl sulfones

Herein we report a mild, general protocol for visible-light-mediated alkylation of 4-alkyl-1,4-dihydropyridines with alkenyl sulfones. The protocol permits efficient functionalization of sulfones with a broad range of cyclic and acyclic secondary and tert

PhB(OH)2-Promoted Electrochemical Sulfuration-Formyloxylation of Styrenes and Selectfluor-Mediated Oxidation-Olefination

We report a PhB(OH)2-promoted electrochemical sulfuration-formyloxylation reaction of styrenes employing commercially available thiophenols/thiols as thiolating agents. Specifically, metal catalysts and external chemical oxidants are not needed in the reaction for the formation of β-formyloxy sulfides, and these sulfides can be further converted to (E)-vinyl sulfones via the Selectfluor-mediated oxidation-olefination. Notably, on the basis of this electrochemical oxidation strategy, β-hydroxy sulfide, β-formyloxy sulfoxide, β-formyloxy sulfone, and (E)-vinyl sulfoxide can also be easily prepared.

Vinyl sulfone synthesisviacopper-catalyzed three-component decarboxylative addition

The synthesis of vinyl sulfone derivativesviathe reaction of arylpropiolic acids, K2S2O5, and aryl boronic acids is reported. The CuBr2/1,10-phenanthroline catalytic system in the presence of acetic acid provide

Intermolecular [2 + 2] Photocycloaddition of α,β-Unsaturated Sulfones: Catalyst-Free Reaction and Catalytic Variants

2-Aryl-1-sulfonyl-substituted cyclobutanes were prepared in an intermolecular [2 + 2] photocycloaddition from various α,β-unsaturated sulfones and olefins upon irradiation at λ = 300 nm (26 examples, 60-99% yield). Lewis acids catalyzed the [2 + 2] photocycloaddition of 2-benzimidazolyl styryl sulfones. At short wavelengths, the latter substrates underwent C-S bond cleavage but AlBr3 (5 mol %) allowed for an intermolecular reaction with 2,3-dimethyl-2-butene at longer wavelengths. A chiral-at-metal Lewis acid (2 mol %) facilitated an enantioselective reaction (up to 77% ee).

N,N′-Disulfonylhydrazines: New sulfonylating reagents for highly efficient synthesis of (E)-vinyl sulfones at room temperature

N,N′-Disulfonylhydrazines have been proven to be the most reactive precursors of sulfonyl radicals in all types of sulfonyl substituted hydrazines as early as a half century ago. But such function has not been applied in organic synthesis except the formation of disulfones by self-dimerization of sulfonyl radicals. In this article, they were introduced as new sulfonylating reagents and their combinations with NIS and Et3N were established as excellent iodosulfonylating reagents for alkenes. Finally, a highly efficient method for the synthesis of (E)-vinyl sulfones was developed by mixing an alkene, a N,N′-disulfonylhydrazine, NIS and Et3N in THF at room temperature for 5 min.

Base-controlled divergent synthesis of vinyl sulfones from (benzylsulfonyl)benzenes and paraformaldehyde

A tuneable metal-free protocol for the selective preparation of a-substituted vinyl sulfone and (E)-vinyl sulfone derivatives has been described. In this process, stable paraformaldehyde was used as the carbon source. The base played an important role in the selectivity control of transformations. More than 50 products were synthesized with excellent chemoselectivity and broad functional group tolerance.