Fluolead™: Everything that DAST Will Do … And More That It Won’t

by catylixinc

Catylix is the sole primary North American manufacturer source of Fluolead (4-tert-Butyl-2,6-dimethylphenylsulfur trifluoride).

CAS # 9947725-04-4

The fluorinating reagent has proven to be more versatile, more stable, and easier to handle than Deoxofluor, DAST, and analogs for a variety of fluorination reactions. Fluolead™ is particularly advantageous for high-yielding gem-difluorinations of carbonyl groups with minimal side product formation due to elimination of HF.

Fluolead will do everything that DAST, Xtalfluor, deoxofluor, and similar reagent can do, and much more. Fluolead is more thermally stable and easier to handle. Fluolead is soluble in most organic solvents. And Fluolead carries out fluorination reactions (for example -COOH to -CF3 and -C=O to -CF2 that cannot be achieved nearly as efficiently with other reagents.

Fluolead reactions

 

In 2010, Umemoto reported an air-stable, thermostable alternative to common fluorinating agents such as DAST for the conversion of hydroxyl to fluorides and and carbonyl groups to gem-difluorides. The reagent 4-tert-Butyl-2,6-dimethylphenylsulfur trifluoride was trade-named Fluolead™.1 This reagent has proved to be very versatile reacting with a variety of hydroxyl and carbonyl groups yielding the corresponding fluorinated products in good to high yields. Fluolead™, a white to off-white crystalline material, also showed high thermal stability and high resistance to aqueous hydrolysis. Extensive studies have been conducted using DSC and ARC to evaluate the thermal stability of Fluolead™. These studies conclusively show the highest thermal stability of Fluolead™ compared to DAST and Deoxo-fluor™. In particular, it showed that Fluolead™ has an excellent thermal stability above 150 °C, which makes it the most stable deoxofluorination reagent to date. It gives Fluolead™ the ability to be used in reactions requiring temperatures in excess of 100 °C, commonly used for the conversion of carboxylic acids to trifluoromethyl groups. More importantly, these results illustrate the suitability of Fluolead™ for deoxofluorination reactions on commercial scales.

Reference: Umemoto, T. et al. J. Am. Chem. Soc. 2010, 132, 18199

Fluolead™ is a trademark of UBE America, Inc.

Contact Catylix for your requirements for additional information. Fluolead™ is available from grams to multi-tons only from Catylix, Inc.

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