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

A15574 Pentafluorophenol, 99%

CAS-Nummer
771-61-9
Synonyme
PFP

Größe Preis ($) Menge Verfügbarkeit
5g 28,74
25g 97,20
100g 357,41
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Pentafluorophenol, 99%

MDL
MFCD00002156
EINECS
212-235-8

Chemische Eigenschaften

Formel
C6HF5O
Molmasse
184.06
Schmelzpunkt
32-36°
Siedepunkt
143°
Flammpunkt
72°(161°F)
Dichte
1.757
Brechungsindex
1.4270
Löslichkeit
Soluble in water.

Anwendungen

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.

Bemerkungen

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

Literaturverweise

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 Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H302-H312-H315-H319-H335

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

Sicherheitshinweise: 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.

Weitere Referenzen

Beilstein
1912584
Harmonized Tariff Code
2908.19
TSCA
Yes
RTECS
SM6680000

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