15296-88-5

Usage

Uses

Used in Pharmaceutical Industry:
[bromo(phenyl)methyl]sulfonylbenzene is used as a pharmaceutical intermediate for the synthesis of various organic compounds. Its unique chemical structure allows for the creation of specialized compounds that can be utilized in the development of new medications and therapies.
Used in Agrochemical Industry:
In the agrochemical industry, [bromo(phenyl)methyl]sulfonylbenzene is used as a building block for the synthesis of target molecules that can be applied in the development of pesticides, herbicides, and other agricultural chemicals. Its versatility in organic synthesis makes it a valuable component in the creation of effective and environmentally friendly agrochemicals.
Used in Organic Synthesis Research:
[bromo(phenyl)methyl]sulfonylbenzene is also used as a research compound in the field of organic synthesis. Its reactivity and structural features make it an attractive candidate for the development of new synthetic methods and the exploration of novel chemical reactions. Researchers and chemists can leverage {[bromo(phenyl)methyl]sulfonyl}benzene to study and understand complex organic transformations, potentially leading to the discovery of new synthetic pathways and applications.

Upstream product

• 79916-85-1 α,α-dibromobenzyl phenyl sulfone 
• 3112-88-7 Benzyl phenyl sulfone 
• 7417-81-4 benzyl phenyl sulfoxide 
• 100-39-0 benzyl bromide 
• 873-55-2 sodium benzenesulfonate 
• 70683-04-4 α-benzenesulfonyl-phenylacetic acid 
• 26910-39-4 α-Brommethylphenyl-phenylsulfoxid 
• 831-91-4 Benzyl phenyl sulfide 

Downstream Products

• 3112-88-7 Benzyl phenyl sulfone 
• 76160-90-2 9,9'-bisphenylthio-9,9'bifluorenyl 

Relevant academic research and scientific papers

Alkyl Halides via Visible Light Mediated Dehalogenation

Net selective bromination and chlorination of activated C-H bonds can be effected in generally high yield via a simple perhalogenation/dehalogenation sequence. The photochemical reductions require no photocatalyst, relying instead on the formation of an electron donor-acceptor complex of the substrate and reductant, or alternatively autophotocatalysis. Some reactions proceed despite any apparent photon absorption, serving as a cautionary tale for other photochemical reactions involving amines. Mechanistic experiments provide an explanation for this observation.

Controlled α-mono- and α,α-di-halogenation of alkyl sulfones using reagent-solvent halogen bonding

The direct and selective α-mono-bromination of alkyl sulfones was achieved through base-mediated electrophilic halogenation. The appropriate combination of solvent and electrophilic bromine source was found to be critical to control the nature of the products formed, where reagent-solvent halogen bonding is proposed to control the selectivity via alteration of the effective size of the electrophilic bromine source. Conversely, the α,α-di-brominated sulfones were selectively obtained in good yields following polyhalogenation followed by selective de-halogenation during workup. Both procedures can be applied on gram scale, and the mono-halogenation was successfully extended to the fully selective α-chlorination, α-iodination and α-fluorination of alkyl sulfones.

Unexpected differences in the α-halogenation and related reactivity of sulfones with perhaloalkanes in KOH-t-BuOH

Most alkyl phenyl sulfones are readily α-chlorinated with CCl4 and α-brominated with CBrCl3 in KOH-t-BuOH via radical-anion radical pair (RARP) reactions. While isopropyl mesityl sulfone (4) is easily α-chlorinated with CCl4, it was completely recovered when treated with the more reactive CBrCl3. Subsequent investigations showed the latter result to be due to the poor acidity of 4 together with the rapid depletion of CBrCl3 and KOH by their reaction with each other, and led to a variety of other important results. 4-Hydroxyphenyl isopropyl sulfone (6) is unreactive with either CCl4 or CBrCl3 in KOH-t-BuOH, its phenoxide anion strongly reducing the electronegativity of the sulfonyl group, thereby inhibiting α-anion formation. This effect is reversed by the electron-withdrawing influence of two α-phenyls, so that benzhydryl 4-hydroxyphenyl sulfone (8) is readily α-halogenated in KOH-t-BuOH with CCl4 or CBrCl3. On further contact with KOH-t-BuOH the α-halogenated sulfones from 8 are decomposed into benzophenone and phenol. While the α-halogenated derivatives of 4-methoxyphenyl benzhydryl sulfone (9) are stable to base, they are decomposed even under mildly acidic conditions into 4-methoxyphenyl 4-methoxybenzenethiolsulfonate (9c), phenol, and benzophenone. Mono-α-halogenation of benzyl phenyl sulfone (10) enhances the rate of the subsequent halogenation, so that α,α-dihalogenation is attained while much substrate is still present and the mono-α-halogenated product is not detected. The ease of reductive debromination of α-bromo sulfones with Cl3C- was correlated with the stability of the formed α-anions, explaining the success with α-bromobenzylic sulfones but failure with α-bromoalkyl sulfones. In the presence of air and the absence of competing halogenation, formation of the α-anions of alkyl aryl sulfones is quickly accompanied by oxidative cleavage by atmospheric O2, leading to the formation of arenesulfonyl alcohols, arenesulfonyl halides, and haloarenes.