Pentafluorobenzoic acid (PFBA) is an

organofluorine compound Organofluorine chemistry describes the chemistry of the organofluorines, organic compounds that contain the carbon–fluorine bond. Organofluorine compounds find diverse applications ranging from oil and water repellents to pharmaceuticals, r ...

with the formula C₆F₅CO₂H. It is a white crystalline powder that has a high solubility in water. Its pK_a of 1.48 indicates that it is a strong acid.Prakash, G. K. S.; Hu, J. "Pentafluorobenzoic Acid" in '' e-EROS Encyclopedia of Reagents for Organic Synthesis'', 2005.

Preparation

Pentafluorobenzoic acid is prepared by treating pentafluorophenyllithium (or pentafluorophenyl Grignard reagent) with carbon dioxide. These reagents are usually prepared in situ from

pentafluorobenzene Pentafluorobenzene is an organofluoride compound with the molecular formula . The compound consists of a benzene ring substituted with five fluorine atoms. The substance is a colorless liquid with a boiling point similar to that of benzene.''CRC H ...

and bromopentafluorobenzene. It arises via the reaction of

perfluorotoluene Perfluorotoluene or octafluorotoluene is a chemical which belongs to the class of fluorocarbons, sometimes referred to as perfluorocarbons or PFCs. Fluorocarbons and their derivatives are useful fluoropolymers, refrigerants, solvents, and anest ...

with

trifluoroacetic acid Trifluoroacetic acid (TFA) is an organofluorine compound with the chemical formula CF3CO2H. It is a structural analogue of acetic acid with all three of the acetyl group's hydrogen atoms replaced by fluorine atoms and is a colorless liquid with ...

and antimony pentafluoride.

Substitution reactions

Substitution of fluoride occurs typically at the para position. This reaction has been used to anchor the −C₆F₄CO₂H group to surfaces. Magnesium methoxide results in ortho methoxylation. Cleavage of this ether gives tetrafluorosalicylic acid. Via similar ortho-directed reactivity, nickel complexes catalyse the defluoridation of 2 and 5 positions. Without nickel, defluoridation occurs with para-selectivity.

References

{{Reflist Benzoic acids Perfluorinated compounds Pentafluorophenyl compounds