22898-07-3

Usage

Uses

Used in Chemical Synthesis:
Benzene, 1-bromo-4-(ethenylsulfonyl)is used as a reactive intermediate in chemical synthesis, particularly for the production of various organic compounds. Its bromine atom facilitates reactions such as substitution and addition, making it a valuable component in the synthesis of new molecules.
Used in Pharmaceutical Development:
In the pharmaceutical industry, Benzene, 1-bromo-4-(ethenylsulfonyl)is used as a building block for the development of new drugs. The sulfonyl group in its structure can be key in the formation of bioactive molecules, potentially leading to the creation of novel therapeutic agents.
Used in Research and Development:
Benzene, 1-bromo-4-(ethenylsulfonyl)is employed in research settings to study the effects of its structural components on chemical reactivity and bioactivity. This can help in understanding the underlying mechanisms of action and potential applications in various fields.

Upstream product

• 106-53-6 para-bromobenzenethiol 
• 14703-92-5 4-(2-hydroxyethylthio)bromobenzene 
• 107737-89-3 4-(2-hydroxyethylsulfonyl)bromobenzene 
• 420-12-2 thirane 
• 98-58-8 4-bromobenzenesulfonyl chloride 
• 26732-25-2 1-bromo-4-(2-chloroethylsulfonyl)benzene 

Downstream Products

• 94243-50-2 3-(4-Bromo-benzenesulfonyl)-4,5-dihydro-1H-pyrazole 
• 1404060-99-6 C₈H₇BrO₃S 
• 109384-79-4 [(1S,2R)-2-(4-Bromo-benzenesulfonyl)-cyclopropyl]-(4-chloro-phenyl)-methanone 
• 109384-80-7 [(1S,2R)-2-(4-Bromo-benzenesulfonyl)-cyclopropyl]-p-tolyl-methanone 
• 63858-81-1 4-{1-[2-(4-bromo-benzenesulfonyl)-ethyl]-4a-methyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl}-morpholine 
• 63858-80-0 4-{3-[2-(4-bromo-benzenesulfonyl)-ethyl]-4a-methyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl}-morpholine 
• 57847-78-6 4-[2-(4-bromo-benzenesulfonyl)-decahydro-cyclobuta[b]naphthalen-2a-yl]-morpholine 
• 63858-84-4 4-[2-(4-bromo-benzenesulfonyl)-ethyl]-morpholine 

Relevant academic research and scientific papers

Metal-free visible-light-promoted C(sp3)-H functionalization of aliphatic cyclic ethers using trace O2

Presented is a light-promoted C-C bond forming reaction yielding sulfone and phosphate derivatives at room temperature in the absence of metals or photoredox catalyst. This transformation proceeds in neat conditions through an auto-oxidation mechanism which is maintained through the leaching of trace amounts of O2 as sole green oxidant. This journal is

Safe and Metal-Free Synthesis of 1-Alkenyl Aryl Sulfides and Their Sulfones from Thiiranes and Diaryliodonium Salts

A series of 1-alkenyl aryl sulfides was synthesized from thiiranes and diaryliodonium salts in tetrahydrofuran in the presence of potassium tert -butoxide. The proposed reaction mechanism involves generation of benzynes from the diaryliodonium salts in the presence of the base. Then, nucleophilic attack of the benzynes by thiiranes, followed by hydrogen abstraction and ring opening of the generated thiiranium intermediates, provides the sulfides. These sulfides were further oxidized with performic acid to the corresponding sulfones. The current method provides a metal-free and safe method for the preparation of 1-alkenyl aryl sulfides and their sulfones.

Design, Synthesis, and Evaluation of 2-(arylsulfonyl)oxiranes as Cell-permeable Covalent Inhibitors of Protein Tyrosine Phosphatases

A structure-based design approach has been applied to develop 2-(arylsulfonyl)oxiranes as potential covalent inhibitors of protein tyrosine phosphatases. A detailed kinetic analysis of inactivation by these covalent inhibitors reveals that this class of compounds inhibits a panel of protein tyrosine phosphatases in a time- and dose-dependent manner, consistent with the covalent modification of the enzyme active site. An inactivation experiment in the presence of sodium arsenate, a known competitive inhibitor of protein tyrosine phosphatase, indicated that these inhibitors were active site bound. This finding is consistent with the mass spectrometric analysis of the covalently modified protein tyrosine phosphatase enzyme. Additional experiments indicated that these compounds remained inert toward other classes of arylphosphate-hydrolyzing enzymes, and alkaline and acid phosphatases. Cell-based experiments with human A549 lung cancer cell lines indicated that 2-(phenylsulfonyl)oxirane (1) caused an increase in intracellular pTyr levels in a dose-dependent manner thereby suggesting its cell-permeable nature. Taken together, the newly identified 2-(arylsulfonyl)oxiranyl moiety could serve as a novel chemotype for the development of activity-based probes and therapeutic agents against protein tyrosine phosphatase superfamily of enzymes.