20621-29-8 | Trifluoromethanesulfinyl Chloride

CAS:20621-29-8 | Trifluoromethanesulfinyl Chloride ,Description

Trifluoromethanesulfinyl chloride (TFMSCl) is a highly reactive and versatile organofluorine compound used in a variety of chemical and pharmaceutical applications. It is a colorless liquid with a pungent odor, and is a member of the family of sulfonyl chlorides. The compound has a wide range of uses, from the synthesis of pharmaceuticals to the production of fluorinated polymers and other materials. It is also used in the synthesis of fluorinated compounds, such as trifluoromethanesulfonyl fluoride (TFMSF), and in the production of fluorinated surfactants.
 

Scientific Research Applications

Electrophilic Trifluoromethylthiolation

CF3SOCl is a novel reagent for C-H trifluoromethylthiolation of organic compounds like indoles, thiophenes, and ketones. It functions under catalyst-free conditions, without the need for a reductant, and provides pathways for trifluoromethylthiolation through either direct trifluoromethylthiolation with CF3SCl or trifluoromethylsulfoxidation with CF3SOCl. This process can also be extended to functionalize other organic compounds under the promotion of certain catalysts like Ag2CO3 (Jiang et al., 2018).

Trifluoromethylation and Sulfenylation/Sulfinylation

CF3SOCl, in combination with sodium trifluoromethanesulfinate (CF3SO2Na), is widely used for the direct trifluoromethylation of a broad spectrum of substrates. These reagents are instrumental in trifluoromethylsulfenylation and trifluoromethylsulfinylation processes, introducing SCF3 and S(O)CF3 groups, respectively. Their versatility extends to other reactions such as sulfonylation and chlorination (Guyon et al., 2017).

Catalytic Acylation and Macrolactonization

Scandium trifluoromethanesulfonate, a derivative of trifluoromethanesulfonyl chloride, serves as an extremely active Lewis acid catalyst. It is particularly effective in catalyzing the acylation of alcohols with acid anhydrides or esterification of alcohols by carboxylic acids. The high catalytic activity is also beneficial for selective macrolactonization of omega-hydroxy carboxylic acids, providing a useful method in synthetic chemistry (Ishihara et al., 1996).

Trifluoromethylsulfinylation

The monoreduction of trifluoromethanesulfonyl chloride by specific phosphines generates trifluoromethanesulfinyl chloride, which acts as a donor of the CF3S(O)+ cation. This enables direct trifluoromethylsulfinylation of various organic compounds, showcasing its potential in the field of organic synthesis (Chachignon & Cahard, 2017).

Analytical Applications

Trifluoromethanesulfonyl chloride is also utilized in analytical chemistry, particularly in fluorine-19 nuclear magnetic resonance spectrometry. It forms stable compounds with tertiary nitrogen bases and yields sulfonation products with active hydrogen-containing compounds, aiding in the determination of organic structure and functionality (Shue & Yen, 1982).

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