947725-04-4

Usage

Uses

Used in Chemical Synthesis:
4-tert-Butyl-2,6-dimethylphenylsulfur Trifluoride is used as a deoxofluorination reagent for the synthesis of arylsulfur trifluorides, offering an improved method that enhances the overall process.
Used in Industrial Production:
4-tert-Butyl-2,6-dimethylphenylsulfur Trifluoride is used as a novel fluorinating reagent in various chemical processes, including industrial scale production, due to its excellent thermal stability, up to 150 °C, and its ability to promote nucleophilic deoxofluorination reactions.
For more information on 4-tert-Butyl-2,6-dimethylphenylsulfur Trifluoride, refer to the Datasheet for Fluolead: A Novel New Versatile Fluorinating Agent.

Upstream product

• 98-19-1 5-tert-Butyl-m-xylene 
• 68819-90-9 bis(4-tert-butyl-2,6-dimethylphenyl) disulfide 

Downstream Products

• 1259294-12-6 N-(4-tert-butyl-2,6-dimethylphenylsulfinyl)-3-fluoropiperidine 
• 1259293-90-7 N-(2-fluoroethyl)-N-methyl-4-tert-butyl-2,6-dimethylbenzensulfinamide 
• 1207990-88-2 4-tert-butyl-2,6-dimethylbenzenesulfinyl fluoride 
• 1207991-16-9 N-(4-tert-butyl-2,6-dimethylphenylsulfonyl)-3-fluoropyrrolidine 
• 1207989-71-6 2-fluoro-2-phenylethyl 4-tert-butyl-2,6-dimethylbenzenesulfinate 
• 1207989-62-5 2-fluoropropyl 4-tert-butyl-2,6-dimethylbenzenesulfinate 
• 1259294-10-4 2-fluoro-1-methylethyl 4-ert-butyl-2,6-dimethylbenzenesulfinate 
• 1259294-04-6 4-fluorobutyl 4-tert-butyl-2,6-dimethylbenzenesulfinate 
• 1207990-50-8 N-(2-fluoroethyl)-N-benzyl-4-tert-butyl-2,6-dimethylbenzensulfinamide 
• 1207990-03-1 3-fluoropropyl 4-tert-butyl-2,6-dimethylbenzenesulfinate 
• 1207990-05-3 4-fluoro-2-[4-tert-butyl-2,6-dimethylbenzenesulfinyloxy]pentane 
• 1229603-71-7 2,7-dibromo-9,9-difluoro-9H-fluorene 
• 1449225-57-3 ethyl 4-tert-butyl-2,6-dimethylphenylsulfinate 
• 1449225-58-4 ethyl 4-tert-butyl-2,6-dimethylphenylsulfonate 

Relevant academic research and scientific papers

Method of Synthesis of Arylsulfur Trifluorides and Use as in situ Deoxofluorination Reagent

The invention is a method of synthesizing Arylsulfur Trifluorides, such as Fluolead, by reacting BR2 and KF (or suitable alkali metal fluoride) in acetonitrile (or other suitable solvent). The invention also comprises using the Fluolead (or its

Discovery of 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride as a deoxofluorinating agent with high thermal stability as well as unusual resistance to aqueous hydrolysis, and its diverse fluorination capabilities including deoxofluoro-arylsulfinylation with high stereoselectivity

Versatile, safe, shelf-stable, and easy-to-handle fluorinating agents are strongly desired in both academic and industrial arenas, since fluorinated compounds have attracted considerable interest in many areas, such as drug discovery, due to the unique effects of fluorine atoms when incorporated into molecules. This article describes the synthesis, properties, and reactivity of many substituted and thermally stable phenylsulfur trifluorides, in particular, 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride (Fluolead, 1k), as a crystalline solid having surprisingly high stability on contact with water and superior utility as a deoxofluorinating agent compared to current reagents, such as DAST and its analogues. The roles of substiuents on 1k in thermal and hydrolytic stability, fluorination reactivity, and the high-yield fluorination mechanism it undergoes have been clarified. In addition to fluorinations of alcohols, aldehydes, and enolizable ketones, 1k smoothly converts non-enolizable carbonyls to CF2 groups, and carboxylic groups to CF3 groups, in high yields. 1k also converts C(=S) and CH3SC(=S)O groups to CF2 and CF3O groups, respectively, in high yields. In addition, 1k effects highly stereoselective deoxofluoro-arylsulfinylation of diols and amino alcohols to give fluoroalkyl arylsulfinates and arylsulfinamides, with complete inversion of configuration at fluorine and the simultaneous, selective formation of one conformational isomer at the sulfoxide sulfur atom. Considering the unique and diverse properties, relative safety, and ease of handling of 1k in addition to its convenient synthesis, it is expected to find considerable use as a novel fluorinating agent in both academic and industrial arenas.

SUBSTITUTED PHENYLSULFUR TRIFLUORIDE AND OTHER LIKE FLUORINATING AGENTS

Novel substituted phenylsulfur trifluorides that act as fluorinating agents are disclosed. Also disclosed are methods for their preparation and methods for their use in introducing one or more fluorine atoms into target substrate compounds.

Substituted phenylsulfur trifluoride and other like fluorinating agents

Novel substituted phenylsulfur trifluorides that act as fluorinating agents are disclosed. Also disclosed are methods for their preparation and methods for their use in introducing one or more fluorine atoms into target substrate compounds.