421-83-0 | Trifluoromethanesulfonyl chloride

CAS:421-83-0 | Trifluoromethanesulfonyl chloride ,Description

Trifluoromethanesulfonyl chloride (TFMSCl) is an important reagent in synthetic organic chemistry, used in a variety of reactions and applications. It is a highly versatile and reactive compound that has a wide range of uses in the laboratory. TFMSCl is a colorless, volatile liquid with a pungent odor. It is a strong halogenating agent and is highly reactive with other compounds, making it a powerful reagent for a variety of reactions.
 

Scientific Research Applications

Trifluoromethylation and Other Reactions

CF3SO2Cl is extensively used for direct trifluoromethylation of various substrates. It is also employed for trifluoromethylsulfenylation, trifluoromethylsulfinylation, sulfonylation, and chlorination. This versatility allows for the introduction of SCF3 and S(O)CF3 groups into different compounds, enhancing their properties for various applications (Guyon, Chachignon, & Cahard, 2017).

NMR Spectrometry

CF3SO2Cl is useful in fluorine-19 nuclear magnetic resonance (NMR) spectrometry. It aids in identifying oxygen, nitrogen, and sulfur functional groups in organic compounds. This application is significant for structural analysis and functional determination in organic chemistry (Shue & Yen, 1982).

Electrophilic Trifluoromethylthiolation

The compound finds application in regioselective trifluoromethylthiolation under reductive conditions, offering a metal-free process. This is particularly relevant for the trifluoromethylthiolation of indole derivatives, azaarenes, enamines, and enoxysilanes (Chachignon et al., 2016).

Lewis Acid Catalysis

CF3SO2Cl is related to scandium trifluoromethanesulfonate, a potent Lewis acid catalyst. This compound is used for acylation of alcohols with acid anhydrides and esterification of alcohols by carboxylic acids, significantly enhancing catalytic activities (Ishihara, Kubota, Kurihara, & Yamamoto, 1996).

Novel Reagent Applications

CF3SO2Cl serves as a reagent for various chemical transformations. This includes its use in the synthesis of triflamides and triflimides, acting as a source of nitrogen in C-amination reactions. These compounds are important in organic synthesis, medicine, biochemistry, catalysis, and agriculture (Moskalik & Astakhova, 2022).

Vinyl and Aryl Triflates Synthesis

CF3SO2Cl contributes to the synthesis of vinyl and aryl triflates, important in cross-coupling reactions and natural product synthesis. It facilitates the preparation of these compounds, leading to enhanced regio- and diastereoselectivity in reactions (Ritter, 1993).

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