17447-59-5

Basic information

• Product Name: diphenylmethyl 4-methylbenzenesulfinate
• CAS NO: 17447-59-5
• Molecular Formula: C₂₀H₁₈O₂S
• Molecular Weight: 322.4207
• Mol File: 17447-59-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 485.6°C at 760 mmHg
• Flash Point: 247.5°C
• Density: 1.24g/cm³
• Vapor Pressure: 4.12E-09mmHg at 25°C
• Refractive Index: 1.661
• CAS DataBase Reference: diphenylmethyl 4-methylbenzenesulfinate(CAS DataBase Reference)
• NIST Chemistry Reference: diphenylmethyl 4-methylbenzenesulfinate(17447-59-5)
• EPA Substance Registry System: diphenylmethyl 4-methylbenzenesulfinate(17447-59-5)

Safety Data

• Hazardous Substances Data: 17447-59-5(Hazardous Substances Data)

Usage

General Description

Diphenylmethyl 4-methylbenzenesulfinate is a white to light yellow solid chemical compound that is used as a reagent in organic synthesis. It is a sulfinate ester, which means it contains a sulfur atom attached to a carbon atom through a double bond. diphenylmethyl 4-methylbenzenesulfinate is commonly used as a source of the sulfinyl group in various reactions, such as in the synthesis of sulfoxides and sulfones. It is also utilized in the preparation of chiral ligands and catalysts for asymmetric synthesis. Furthermore, diphenylmethyl 4-methylbenzenesulfinate has been studied for its potential applications in the development of new pharmaceutical drugs and materials. Overall, this chemical compound has diverse uses and plays an important role in organic chemistry research and industrial processes.

Upstream product

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

Relevant articles and documents

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.

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.