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Pentafluorophenol

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Pentafluorophenol
Names
Preferred IUPAC name Pentafluorophenol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.123 Edit this at Wikidata
EC Number
  • 212-235-8
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6HF5O/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12HKey: XBNGYFFABRKICK-UHFFFAOYSA-N
SMILES
  • C1(=C(C(=C(C(=C1F)F)F)F)F)O
Properties
Chemical formula C6F5OH
Molar mass 184.065 g·mol
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:
Pictograms GHS05: CorrosiveGHS07: Exclamation mark
Signal word Danger
Hazard statements H302, H312, H314, H315, H319, H335
Precautionary statements 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 , 100 kPa). Infobox references
Chemical compound

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.

Uses

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

Environmental hazards

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

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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