947725-04-4 | 4-tert-Butyl-2,6-dimethylphenylsulfur Trifluoride

CAS:947725-04-4 | 4-tert-Butyl-2,6-dimethylphenylsulfur Trifluoride ,Description

4-tert-Butyl-2,6-dimethylphenylsulfur Trifluoride (4-TBMPSF) is a highly versatile and multifunctional compound that is used in a wide range of scientific applications. It is a colorless liquid that has a wide range of applications in organic synthesis, material science, and biochemistry. 4-TBMPSF is a highly reactive compound that can be used for a variety of synthetic and analytical purposes. It is also used in a variety of biochemical and physiological applications, such as in the synthesis of enzymes and other biological molecules.
 

Scientific Research Applications

Novel Fluorinating Agent

4-tert-Butyl-2,6-dimethylphenylsulfur trifluoride, identified as Fluolead (1k), is a crystalline solid known for its high stability upon contact with water and excellent utility as a deoxofluorinating agent, surpassing traditional reagents like DAST and its analogs. The compound's synthesis, thermal and hydrolytic stability, fluorination reactivity, and mechanism have been thoroughly investigated. Fluolead efficiently fluorinates alcohols, aldehydes, enolizable and non-enolizable ketones, carboxylic groups, converting them to CF(2) or CF(3) groups, and demonstrates superior yields. Additionally, it has shown remarkable capabilities in highly stereoselective deoxofluoro-arylsulfinylation of diols and amino alcohols, leading to fluoroalkyl arylsulfinates and arylsulfinamides with complete inversion at the fluorine atom and selective sulfoxide sulfur atom conformation. This breadth of applications, combined with its safety, ease of handling, and synthesis, positions Fluolead as a valuable fluorinating agent in both academic and industrial settings (Umemoto, Singh, Xu, & Saito, 2010).

Rhodium-Catalyzed Synthesis of Diaryl Sulfides

The research also highlights the utility of di-tert-butyl tetrasulfide, a compound related to the 4-tert-Butyl-2,6-dimethylphenylsulfur trifluoride, in the Rhodium-catalyzed synthesis of diaryl sulfides. This process involves the reaction of substituted pentafluorobenzenes with sulfur in the presence of Rhodium catalysts, leading to bis(4-substituted 2,3,5,6-tetrafluorophenyl) sulfides. The study delves into the comparative reactivity of organic trisulfides and tetrasulfides, showing di-tert-butyl tetrasulfide's specific reactivity with aryl monofluorides and substituted pentafluorobenzenes, providing insights into substrate specificity and the influence of S-S bond energy on reactivity (Arisawa, Ichikawa, & Yamaguchi, 2012).

More Information