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The first to investigate trifluoromethyl groups in relationship to biological activity was F. Lehmann in 1927. [5] An early review appeared in 1958. [6] An early synthetic method was developed by Frédéric Swarts in 1892, [7] based on antimony fluoride.
Trifluoromethyltrimethylsilane (known as Ruppert-Prakash reagent, TMSCF 3) is an organosilicon compound with the formula CF 3 Si(CH 3) 3.It is a colorless liquid. The compound is a reagent used in organic chemistry for the introduction of the trifluoromethyl group.
Togni reagent II (1-trifluoromethyl-1,2-benziodoxol-3(1H)-one) is a chemical compound used in organic synthesis for direct electrophilic trifluoromethylation. [ 1 ] [ 2 ] History
Sodium trifluoromethanesulfinate (CF 3 SO 2 Na) is the sodium salt of trifluoromethanesulfinic acid. Together with t-butyl hydroperoxide, an oxidant, this compound was found to be a suitable reagent for introducing trifluoromethyl groups onto electron-rich aromatic compounds by Langlois; this reagent is also known as the Langlois reagent.
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. Some common examples are trifluoromethane H– CF 3, 1,1,1-trifluoroethane H ...
In the laboratory, triflic acid is useful in protonations because the conjugate base of triflic acid is nonnucleophilic. It is also used as an acidic titrant in nonaqueous acid-base titration because it behaves as a strong acid in many solvents (acetonitrile, acetic acid, etc.) where common mineral acids (such as HCl or H 2 SO 4) are only moderately strong.
Carboxylic acids react with SF 4 to afford trifluoromethyl compounds: [10] C 6 H 13 CO 2 H + 2 SF 4 → C 6 H 13 CF 3 + 2 SOF 2 + HF. The formation of the trifluoromethyl derivative sometimes competes with formation of tetrafluoroalkyl ethers, which arise from the reaction between difluoromethyl cation and acyl fluoride. [11] [12]
Two other isomers are also known: 2-trifluoromethylbenzaldehyde and 3-trifluoromethylbenzaldehyde. These compounds are derivatives of benzaldehyde with trifluoromethyl substituents. The CF 3 group enhances the electrophilicity of the formyl group and provides a label for analysis by fluorine-19 nuclear magnetic resonance spectroscopy.