Petrofluorophenyl magnesium chloride was prepared by reacting monochloropentafluorobenzene, a byproduct of the preparation of hexafluorobenzene from hexachlorobenzene, with magnesium at a reaction temperature of 45–50 °C for 2.5 h. Triisopropyl borate was used as a borizing agent to prepare dipropyl pentafluorophenylboronic acid at a reaction temperature of -10–-15 °C for 3 h. Dipropyl pentafluorophenylboronic acid was then hydrolyzed under acidic conditions to obtain pentafluorophenylboronic acid. Pentafluorophenylboronic acid was then reacted with hydrogen peroxide to obtain pentafluorophenol at a reaction temperature of 65 °C for 5 h. The resulting product had a purity of over 99.5% (GC), with a three-step yield of 60.25%.
Pentafluorophenol can be used for the preparation of penta-fluorophenyl esters for peptide synthesis. It 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. It can be used for synthesizing novel reagents which can achieve highly diastereoselective acetal cleavage.
3. Ishihara, Kazuaki, N. Hanaki, and H. Yamamoto. "Highly diastereoselective acetal cleavages using novel reagents prepared from organoaluminum and pentafluorophenol" Cheminform 25.9(2010):no-no.
For the preparation of pentafluorophenyl esters for peptide synthesis.
Used for the preparation of pentafluorophenyl esters for peptide synthesis
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.
Pentafluorophenol can be used as a reactant to synthesize pentafluorophenyl esters from:
- N-protected amino acid in the presence of dicyclohexylcarbodiimide and ethyl acetate.
- t-Butoxycarbonyl-L-alanylglycinein the presence of 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride.
- Aliphatic dicarboxylic acids in the presence of pyridine, diisopropylcarbodiimide, and acetonitrile.
It can also be used as a reactant to synthesize pentafluorophenyl formate which can be used as a formylating agent in organic synthesis.
Pentafluorophenol is widely used as a precursor in both solution and
solid-phase peptide synthesis. It is also involved in the preparation of
aromatic fluoro derivatives.
reaction type: Addition Reactions
scu-rat LD50:322 mg/kg IZSBAI 3,91,65
Pentafluorophenol is a hygroscopic low melting solid not freely soluble in H2O. Purify it by distillation, preferably in a vacuum [Forbes et al. J Chem Soc 2019 1959, IR and pKa: Birchall & Haszeldine J Chem Soc 13 1959]. IRofafilmhas max 3600 (OH) and 1575 (fluoroaromatic breathing) cm-1 . The benzoyl derivative has m 74-75o, 3,4-dinitrobenzoyl derivative has m 107o, the tosylate has m 64-65o (from EtOH) and the K salt crystallises from Me2CO, m 242o(dec), with 1H2O-salt the m is 248o(dec) and the 2H2O-salt has m 245o(dec). [Beilstein 6 IV 782.]
