pentafluorophenol

• ChemBase ID: 9652
• Molecular Formular: C6HF5O
• Molecular Mass: 184.063556
• Monoisotopic Mass: 183.99475575
• SMILES: c1(F)c(F)c(O)c(c(c1F)F)F
• Canonical SMILES: Fc1c(O)c(F)c(c(c1F)F)F
• InChI: InChI=1S/C6HF5O/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H
• InChIKey: XBNGYFFABRKICK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: pentafluorophenol
• IUPAC Traditional name: pentafluorophenol
• Synonyms: 2,3,4,5,6-Pentafluorophenol; Pentafluorophenol; Pentafluorophenol; Pentafluorophenol; Perfluorophenol 99%; 2,3,4,5,6-pentafluorophenol; PFP; 2,3,4,5,6-五氟苯酚; 五氟苯酚; 2,3,4,5,6-五氟苯酚

Database IDs

• CAS Number: 771-61-9
• EC Number: 212-235-8
• MDL Number: MFCD00002156
• Beilstein Number: 1912584
• PubChem SID: 160972959; 24846624; 24867998
• PubChem CID: 13041

CALCULATED PROPERTIES

• Acid pKa: 5.765602
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 2.1974938
• LogD (pH = 7.4): 0.904295
• Log P: 2.3831902
• Molar Refractivity: 29.1209 cm^3
• Polarizability: 10.361605 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 32-36°C; 34-36 °C(lit.); 34-36°C
• Boiling Point: 143 °C(lit.); 143°C; 143°C
• Flash Point: 161.6 °F; 72 °C; 72°C; 72°C(161°F)
• Density: 1.757
• Refractive Index: 1.4270

Safety Information

• Storage Warning: TOXIC, CORROSIVE; Toxic/Irritant/Air Sensitive/Store under Argon
• RTECS: SM6680000
• European Hazard Symbols: Corrosive (C); X; Irritant (Xi)
• UN Number: UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: II
• Risk Statements: 21/22-34; 36/37/38
• Safety Statements: 26-36; 26-36/37/39-45
• TSCA Listed: true; 是
• GHS Pictograms: GHS05; GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301-H311-H314-H318; H315-H319-H335
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P361-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99%; 97%; 98%; 99%; 99+%
• Grade: analytical standard; ReagentPlus®
• Packaging: ampule of 1000 mg
• Linear Formula: C6F5OH
• Empirical Formula (Hill Notation): C6HF5O

DETAILS

Apollo Scientific Ltd - PC5630

Useful reagent for peptide coupling via the reactive PFP esters, often prepared by carbodiimide coupling.

Sigma Aldrich - 103799

Application
For the preparation of pentafluorophenyl esters for peptide synthesis.
Packaging
5, 10, 100 g in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

REFERENCES

• Widely used for peptide coupling (see Appendix 6) via the active PFP esters, generally prepared by carbodiimide coupling: Liebigs Ann. Chem., 1421 (1973); Tetrahedron Lett., 1785 (1974). With Fmoc-protected amino acids, the coupling takes place very rapidly, which reduces the amount of Fmoc-cleavage during the peptide bond formation: Synthesis, 325 (1983). Fmoc protected PFP esters have also been applied in solid phase peptide synthesis: Tetrahedron, 44, 843 (1988). PFP esters have been recommended for preparation of derivatives of heterocyclic acids, effective where DCC or DIC alone fail: Synth. Commun., 28, 753 (1998).
• For preparation and use of the moderately stable PFP formate as a formylating agent for amines and amino acids, see: Synthesis, 510 (1987).