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Trifluoromethanesulfonyl chloride (or triflyl chloride, CF3SO2Cl) can be used in a highly efficient method to introduce a trifluoromethyl group to aromatic and heteroaromatic systems, including known pharmaceuticals such as Lipitor. The chemistry is general and mild, and uses a photoredox catalyst and a light source at room temperature. [27]
In organic chemistry, the triflyl group (systematic name: trifluoromethanesulfonyl group) is a functional group with the formula R−SO 2 CF 3 and structure R−S(=O) 2 −CF 3. The triflyl group is often represented by –Tf. The related triflate group (trifluoromethanesulfonate) has the formula R−OSO 2 CF 3, and is represented by –OTf. [1]
The undesired products, by-products chlorine, hydrogen chloride, and chlorotrifluoromethane, can be removed by evaporation at -110 °C. Trifluoromethanol has a melting point of -82 °C and a calculated boiling point of about -20 °C.
For example, n-butyl triflate can be written as CH 3 CH 2 CH 2 CH 2 OTf. The corresponding triflate anion , CF 3 SO − 3 , is an extremely stable polyatomic ion ; this comes from the fact that triflic acid ( CF 3 SO 3 H ) is a superacid ; i.e. it is more acidic than pure sulfuric acid , already one of the strongest acids known.
Trifluoromethanesulfonic anhydride, also known as triflic anhydride, is the chemical compound with the formula (CF 3 SO 2) 2 O. It is the acid anhydride derived from triflic acid . This compound is a strong electrophile , useful for introducing the triflyl group , CF 3 SO 2 .
Trifluoromethyl group covalently bonded to an R group. The trifluoromethyl group is a functional group that has the formula-CF 3.The naming of is group is derived from the methyl group (which has the formula -CH 3), by replacing each hydrogen atom by a fluorine atom.
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Its pK a value in water cannot be accurately determined but in acetonitrile it has been estimated as −0.10 and in 1,2-dichloroethane −12.3 (relative to the pK a value of 2,4,6-trinitrophenol (picric acid), anchored to zero to crudely approximate the aqueous pK a scale [2]), making it more acidic than triflic acid (pK a MeCN = 0.70, pK a DCE ...