- NSC 21627
- Phenol, 2,3,4,5,6-pentafluoro-
- Phenol, pentafluoro-
- PFP is an abbreviation for the pentafluorophenyl group
Physical And Chemical Properties:
Form (appearance): Form is solidified mass or fragments
Color (appearance): Beige
Melting point/freezing point: Melting point/range: 34 -36 °C -lit.
Initial boiling point and boiling range: 143 °C -lit.
Flash point: 72 °C -closed cup
Stability & Reactivity:
Avoid acid anhydrides, acid chlorides, bases and oxidizing agents, but stable under recommended storage conditions.
Pentafluorophenol is a fluorobenzene derivative primarily used to promote coupling to carboxylic and sulfonic acids by activation as a pentafluorophenyl ester. The strong electron-withdrawing character of the 5 fluorine atoms on the benzene ring makes the pentafluorophenolate anion an especially good leaving group. This results in facile coupling of the activated ester with amines and other nucleophiles, minimizing side reactions like racemization of chiral acids, as is often a problem in peptide synthesis.1 Pentafluorophenyl esters are also less sensitive to side reactions like hydrolysis.2 The increased stability of PFP-esters can allow it to serve as a protecting group through several functional group transformations prior to facilitating amidation or sulfonation.3
1 E.Atherton, L.R.Cameron, R.C.Sheppard, Tetrahedron, 1988, 44(3), 843–857.
2 Katz, J., 1998-12-15, “Advances in Peptide Coupling”, Harvard University.
3 J.Kihlberg, M.Elofsson, Current Medicinal Chemistry, 1997, 4(2), 90; B.G. Avitabile, C.A. Smith, D.B. Judd, Org. Lett., 2005, 7(5), 843–846.