Pentafluorophenol

Pentafluorophenol
Names
	Preferred IUPAC name Pentafluorophenol
Identifiers
CAS Number	771-61-9;
3D model (JSmol)	Interactive image;
ChemSpider	12499;
ECHA InfoCard	100.011.123
EC Number	212-235-8;
PubChem CID	13041;
UNII	A2YCF0YUHA;
CompTox Dashboard (EPA)	DTXSID9061120 ;
	InChI InChI=1S/C6HF5O/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H Key: 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−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:
Pictograms
Signal word	Danger
Hazard statements	H302, H312, H314, H315, H319, H335
Precautionary statements	P260, 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

Pentafluorophenol is the organofluorine compound (specifically a fluoroalcohol) with the formula C₆F₅OH. This is the perfluorinated analogue of phenol. It is a white solid that melts just above room temperature, and smells of phenol. With a pK_a of 5.5, it is one of the most acidic phenols and can be easily deprotonated to pentafluorophenolate.

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

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

[1] Jones K, DeAmicis C (2009). "Pentafluorophenol". Encyclopedia of Reagents for Organic Synthesis. pp. 1–9. doi:10.1002/047084289X. hdl:10261/236866.

[sds-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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