79963-95-4 | 2,2,2-Trifluoroethyl Nonafluorobutanesulfonate

CAS:79963-95-4 | 2,2,2-Trifluoroethyl Nonafluorobutanesulfonate ,Description

2,2,2-Trifluoroethyl Nonafluorobutanesulfonate (TFENBS) is an organosulfonic acid that is used as a fluorinating agent in a variety of chemical processes. It is a colorless liquid with a low boiling point and a low vapor pressure. It is soluble in both water and organic solvents, making it an ideal reagent for various industrial and laboratory applications. TFENBS is often used in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. It has also been used in the synthesis of fluorinated polymers and in the production of fluorinated surfactants.
 

Scientific Research Applications

Trifluoromethoxylation Reagent

Trifluoromethyl Nonafluorobutanesulfonate (TFNf) is recognized for its unique properties in drug and agrochemical discovery, serving as an effective trifluoromethoxylating reagent. It is easily and safely prepared, bench-stable, reactive, and scalable. TFNf facilitates the synthesis of trifluoromethoxylated alkenes through high regio- and stereoselective hydro(halo)trifluoromethoxylation of alkyne derivatives, including haloalkynes, alkynyl esters, and alkynyl sulfones. Its synthetic potency is further highlighted in the high-yielding nucleophilic trifluoromethoxylation of alkyl triflates/bromides and primary/secondary alcohols (Lu et al., 2021).

Transition Metal-Catalyzed Reactions

Nonafluorobutanesulfonates are cost-effective intermediates for transition metal-catalyzed reactions, offering many advantages over commonly used triflates. Their application in metal-catalyzed processes such as Heck, Suzuki, Sonogashira, Stille, Negishi couplings, or amination reactions demonstrates their utility in both laboratory and industrial scale organic synthesis. The advantages of nonaflates over triflates in these reactions are significant, indicating their potential for broader applications (Hoegermeier & Reissig, 2009).

Ionic Liquid Applications

Ionic liquids containing nonafluorobutanesulfonate anions exhibit remarkable properties like high ionic conductivity and stability, making them suitable for various applications, including electrochemical devices and fuel cells. The study of these ionic liquids in combination with common cations like 1-ethyl-3-methylimidazolium reveals their potential for enhancing the performance of devices requiring high ionic conductivity and stability at elevated temperatures (Gouveia et al., 2017).

Diazo Transfer and Azide Synthesis

Nonafluorobutanesulfonyl azide has emerged as an efficient, shelf-stable, and cost-effective diazo transfer reagent for synthesizing azides from primary amines. It facilitates one-pot regioselective synthesis of 1,2,3-triazoles from primary amines through sequential diazo transfer and azide-alkyne 1,3-dipolar cycloaddition processes. This method offers a convenient and versatile approach for azide synthesis, which is fundamental in organic synthesis and material science (Suárez et al., 2010) .

Gel Polymer Electrolytes for Lithium-ion Batteries

The use of nonafluorobutanesulfonate-based ionic liquids in gel polymer electrolytes demonstrates significant advancements in lithium-ion battery technology. These electrolytes, incorporating lithium nonafluorobutanesulfonate, show high ionic conductivity and excellent cycling performance, indicating their potential to enhance the efficiency and durability of rechargeable lithium-ion batteries (Karuppasamy et al., 2016).

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