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For small-scale laboratory preparations, trifluorotoluene is synthesized by coupling an aromatic halide and trifluoromethyl iodide in the presence of a copper catalyst: [2] PhX + CF 3 I → PhCF 3 (where X = I, Br) Industrial production is done by reacting benzotrichloride with hydrogen fluoride in a pressurized reactor. [3] PhCCl 3 + 3 HF → ...
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. In this reaction benzotrichloride was reacted with SbF 3 to form PhCF 2 Cl and PhCF 3.
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 ...
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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.
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In contrast, the boiling points of PhF and benzene are very similar, differing by only 4 °C. It is considerably more polar than benzene, with a dielectric constant of 5.42 compared to 2.28 for benzene at 298 K. [4] Fluorobenzene is a relatively inert compound reflecting the strength of the C–F bond.