pentafluorophenol
{{Chembox
| ImageFile = Pentafluorophenol.svg
| ImageSize = 132
| PIN = Pentafluorophenol
|Section1={{Chembox Identifiers
| CASNo = 771-61-9
| PubChem = 13041
| ChemSpiderID = 12499
| EC_number = 212-235-8
| UNII = A2YCF0YUHA
| StdInChI=1S/C6HF5O/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H
| StdInChIKey = XBNGYFFABRKICK-UHFFFAOYSA-N
| SMILES = C1(=C(C(=C(C(=C1F)F)F)F)F)O
}}
|Section2={{Chembox Properties
| Formula = {{chem2|C6F5OH}}
| C=6|H=1|F=5|O=1
| Appearance = white solid or colorless liquid
| MeltingPtC = 32.8
| BoilingPtC = 145.6
}}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS05}}{{GHS07}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|302|312|314|315|319|335}}
| PPhrases = {{P-phrases|260|261|264|270|271|280|301+312|301+330+331|302+352|303+361+353|304+340|305+351+338|310|312|321|322|330|332+313|337+313|362|363|403+233|405|501}}
}}
}}
Pentafluorophenol is the organofluorine compound (specifically a fluoroalcohol) with the formula {{chem2|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 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.{{cite encyclopedia|title=Pentafluorophenol|vauthors=Jones K, DeAmicis C|encyclopedia=Encyclopedia of Reagents for Organic Synthesis|year=2009|pages=1–9|doi=10.1002/047084289X|hdl=10261/236866|hdl-access=free}}
Environmental hazards
Pentafluorophenol is considered hazardous because of oral, dermal and inhalation toxicity and because it causes severe skin burns and eye damage.{{cite web |title=Pentafluorophenol SAFETY DATA SHEET |url=https://www.fishersci.com/store/msds?partNumber=AC147130050&productDescription=PENTAFLUOROPHENOL+99%2B%25+5GR&vendorId=VN00032119&countryCode=US&language=en |publisher=Thermo Fisher Scientific |access-date=26 February 2021 |date=January 18, 2018}}{{cite web |title=Pentafluorophenol |url=https://pubchem.ncbi.nlm.nih.gov/compound/13041#section=Hazards-Identification |website=PubChem |publisher=National Center for Biotechnology Information |access-date=26 February 2021 |date=February 20, 2021}}