Pentafluorophenol

Pentafluorophenol is the organofluorine compound (specifically a fluoroalcohol) with the formula C6F5OH. This is the perfluorinated analogue of phenol. It is a white odorless solid that melts just above room temperature. With a pKa of 5.5, it is one of the most acidic phenols.

Pentafluorophenol
Names
Preferred IUPAC name
Pentafluorophenol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.123
EC Number
  • 212-235-8
UNII
  • InChI=1S/C6HF5O/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H
    Key: XBNGYFFABRKICK-UHFFFAOYSA-N
  • C1(=C(C(=C(C(=C1F)F)F)F)F)O
Properties
C6F5OH
Molar mass 184.065 g·mol−1
Appearance white solid or colorless liquid
Melting point 32.8 °C (91.0 °F; 305.9 K)
Boiling point 145.6 °C (294.1 °F; 418.8 K)
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H312, H314, H315, H319, H335
P260, P261, P264, P270, P271, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Uses

Pentafluorophenol is used to prepare pentafluorophenyl esters, which are active esters useful in peptide synthesis.[1]

Environmental hazards

Pentafluorophenol is considered hazardous because of oral, dermal and inhalation toxicity and because it causes severe skin burns and eye damage.[2][3]

References
  1. Jones K, DeAmicis C (2009). "Pentafluorophenol". Encyclopedia of Reagents for Organic Synthesis. pp. 1–9. doi:10.1002/047084289X. hdl:10261/236866.
  2. "Pentafluorophenol SAFETY DATA SHEET". Thermo Fisher Scientific. January 18, 2018. Retrieved 26 February 2021.
  3. "Pentafluorophenol". PubChem. National Center for Biotechnology Information. February 20, 2021. Retrieved 26 February 2021.
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