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771-61-9 - Pentafluorophenol, 99% - PFP - A15574 - Alfa Aesar

A15574 Pentafluorophenol, 99%

CAS Number
771-61-9
Synonyms
PFP

Size Price ($) Quantity Availability
5g 28.74
25g 97.20
100g 357.41
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Pentafluorophenol, 99%

MDL
MFCD00002156
EINECS
212-235-8

Chemical Properties

Formula
C6HF5O
Formula Weight
184.06
Melting point
32-36°
Boiling Point
143°
Flash Point
72°(161°F)
Density
1.757
Refractive Index
1.4270
Solubility
Soluble in water.

Applications

Pentafluorophenol is used in the preparation of pentafluorophenyl esters for peptide synthesis and vulcanized polymers. It is also used for peptide coupling and heterocyclic acid derivatives. It is involved in the preparation of pentafluorophenyl formate which acts as a formulating agent for amines and amino acids.

Notes

Moisture sensitive. Incompatible with strong oxidizing agents, bases, acid chlorides and acid anhydrides.

Literature 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).

Pandith, A.; Kumar, A.; Kim, H. S. 9-N-Alkylaminomethylanthracene probes for selective fluorescence sensing of pentafluorophenol. RSC Adv. 2015, 5 (100), 81808-81816.

Alonso, J. M.; Fabre, B.; Trilling, A. K.; Scheres, L.; Franssen, M. C.; Zuilhof, H. Covalent Attachment of 1-Alkenes to Oxidized Platinum Surfaces. Langmuir. 2015, 31 (9), 2714-2721.

GHS Hazard and Precautionary Statements

Hazard Statements: H302-H312-H315-H319-H335

Harmful if swallowed. Harmful in contact with skin. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P362-P301+P312-P312-P363-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. Wash contaminated clothing before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
1912584
Harmonized Tariff Code
2908.19
TSCA
Yes
RTECS
SM6680000

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