17447-59-5

Usage

Uses

Used in Organic Synthesis:
Diphenylmethyl 4-methylbenzenesulfinate is used as a source of the sulfinyl group for various chemical reactions, such as the synthesis of sulfoxides and sulfones. Its ability to provide the sulfinyl group makes it a valuable intermediate in the creation of a range of organic compounds.
Used in the Preparation of Chiral Ligands and Catalysts:
In the field of asymmetric synthesis, diphenylmethyl 4-methylbenzenesulfinate is utilized for the preparation of chiral ligands and catalysts. These are essential for enantioselective reactions, which are crucial in producing enantiomerically pure compounds, often required in pharmaceuticals and agrochemicals.
Used in Pharmaceutical Drug Development:
Diphenylmethyl 4-methylbenzenesulfinate has been studied for its potential in the development of new pharmaceutical drugs. Its unique structure and reactivity contribute to the exploration of novel therapeutic agents, particularly in the context of medicinal chemistry.
Used in Material Science:
This chemical compound is also considered for applications in material science, where its properties may be leveraged to develop new materials with specific characteristics, such as improved stability or reactivity in certain conditions.
Overall, diphenylmethyl 4-methylbenzenesulfinate plays a significant role in organic chemistry research and various industrial processes, underpinning its importance across different scientific and technological domains.

Upstream product

• 91-01-0 1,1-Diphenylmethanol 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 536-57-2 p-toluene sulfinic acid 
• 4545-20-4 benzophenone tosylhydrazone 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 

Relevant academic research and scientific papers

N - P -Toluenesulfinylimidazole: A New in situ Reagent for the Mild and Efficient Synthesis of p -Toluenesulfinate Alkyl Esters and Aryl Esters

A new synthetic methodology has been developed for the synthesis of sulfinate alkyl and aryl esters. The methodology involves the combination of p -toluenesulfinic acid and 1,1′-carbonyldiimidazole (CDI) to create the putative reagent sulfinylimidazole. The process spontaneously releases carbon dioxide upon the addition of the CDI to the acid suggesting the rapid formation of the proposed reagent. Reaction of this reagent with a series of alcohols (primary, secondary, and tertiary) afforded the corresponding sulfinate alkyl esters in good to excellent yields by the addition of alcohols. It was also possible to form the related sulfinate aryl esters by treating the proposed sulfinylimidazole with selected phenols (phenol, p - tert -butylphenol, and thymol). The aryl esters were formed in excellent conversion based on analysis of the 500 MHz 1H NMR spectra of the crude reaction mixtures.

Wittig Ylide Mediated Decomposition of N -Sulfonylhydrazones to Sulfinates

N-Sulfonylhydrazones generate sulfinates selectively when treated with a stabilized Wittig ylide in a polar aprotic solvent at elevated temperature. The transition metal and base free decomposition method is applicable to N-sulfonylhydrazones generated from a number of aromatic and heteroaromatic aldehydes and ketones. In the case of N-tosylhydrazones derived from O-allyl and O-propargyl salicylaldehydes, selective formation of sulfinate occurs over intramolecular [3 + 2]-cycloaddition reaction.

Substrate- and temperature-controlled divergence in reactions of alcohols with TosMIC catalyzed by BF3 · Et2O: Facile access to sulfinates and sulfones

An efficient BF3 · Et2O-catalyzed divergent synthesis of sulfinate esters and sulfones through C–O and C–S bond formation has been achieved from alcohols and p-toluenesulfonylmethyl isocyanide (TosMIC). Various alcohols reacted smoothly with TosMIC under the present conditions at room temperature providing sulfinate esters exclusively. By tuning the reaction temperature, the alcohols that provide highly stabilized carbocation in the reaction medium afforded sulfones as sole products. This study was aimed at understanding the regioselectivity of ambidentate sulfinate ion and to elucidate the interpretation of sulfinate/sulfone scaffolds.

Sulfination of alcohols with sodium sulfinates promoted by BF3·OEt2: An unexpected access

A BF3·OEt2-promoted direct substitution of various alcohols with sodium sulfinates affording sulfinates under mild conditions has been developed. Further reaction of the hydroxysteroids achieves the highly complex sulfinates in good yields, which are two potential pharmacophores routinely encountered in drug discovery.

Sulfination of Alcohols with p-Toluenesulfonylmethyl Isocyanide under Metal-Free Conditions: A Mitsunobu Approach

A Mitsunobu approach for the synthesis of sulfinate esters by direct nucleophilic substitution of alcohols is described. The salient features of this strategy include neutral and metal-free conditions for the rapid synthesis of sulfinates in high yields. The present protocol using p-toluenesulfonylmethyl isocyanide (TosMIC) and the triphenylphosphine (TPP)/diisopropyl azodicarboxylate (DIAD) reagent system represents the general synthetic route to this important class of compounds. (Figure presented.).