Pentafluorophenol is the

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

(specifically a

fluoroalcohol Fluoroalcohols are organofluorine compounds consisting of an alcohol functional group with at least one C-F bond. These compounds often have distinctive solvent properties. Perfluoroalcohols Most primary and secondary perfluoroalcohols are unsta ...

) with the formula . This is the perfluorinated analogue of

phenol Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire. The molecule consists of a phenyl group () ...

. It is a white solid that melts just above room temperature, and smells of phenol. With a p''K''_a of 5.5, it is one of the most acidic

Uses

Pentafluorophenol is used to prepare

pentafluorophenyl esters Pentafluorophenyl (PFP) esters are chemical compounds with the generic formula RC(O)OC6F5. They are active esters derived from pentafluorophenol (HOC6F5). PFP esters are useful for attaching fluorophores such as fluorescein or haptens to primary ...

, which are

active ester In organic chemistry, an active ester is an ester functional group that is highly susceptible toward nucleophilic attack. Activation can be imparted by modifications of the acyl or the alkoxy components of a normal ester, say ethyl acetate. Typical ...

s useful in

peptide synthesis In organic chemistry, peptide synthesis is the production of peptides, compounds where multiple amino acids are linked via amide bonds, also known as peptide bonds. Peptides are chemically synthesized by the condensation reaction of the carboxyl ...

Environmental hazards

Pentafluorophenol is considered hazardous because of oral, dermal and inhalation toxicity and because it causes severe skin burns and eye damage.

References

{{Reflist Fluoroarenes Perfluorinated compounds Phenols