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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.
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.
Hazard Statements: H302-H312-H314-H318-H332-H335
Harmful if swallowed. Harmful in contact with skin. Causes severe skin burns and eye damage. Causes serious eye damage. Harmful if inhaled. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P270-P271-P280-P301+P312-P303+P361+P353-P304+P340-P305+P351+P338-P310-P312-P330-P363-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant