Pentafluorobenzene is a fluorinated benzene with anesthetic properties. Pentafluorobenzene has been shown to potently and reversibly inhibited human α4β2 neuronal nicotinic acetylcholine receptor depe ndent on drug hydrophobicity in Xenopus laevis oocyte. New reaction conditions are described that enable the direct arylation of pentafluorobenzene with sterically encumbered aryl bromides and aryl chlorides. Bis (pentafluoropheny1) methane and tris (pentafluoropheny1) methane were prepared in 77 and 92% yields, respectively, by a Friedel-Crafts reaction of pentafluorobenzene with methylene chloride and chloroform using aluminum chloride as the Lewis acid.
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Applications
Pentafluorobenzene is a fluorinated benzene with anesthetic properties. Pentafluorobenzene has been shown to potently and reversibly inhibited human α4β2 neuronal nicotinic acetylcholine receptor depe ndent on drug hydrophobicity in Xenopus laevis oocyte. New reaction conditions are described that enable the direct arylation of pentafluorobenzene with sterically encumbered aryl bromides and aryl chlorides. Bis (pentafluoropheny1) methane and tris (pentafluoropheny1) methane were prepared in 77 and 92% yields, respectively, by a Friedel-Crafts reaction of pentafluorobenzene with methylene chloride and chloroform using aluminum chloride as the Lewis acid.
Solubility
Insoluble in water.
Notes
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from strong oxidizing agents.
RUO – Research Use Only
W. F. Beckert,; James U. LoweJr.. Friedel-Crafts alkylation of pentafluorobenzene. J. Org. Chem.,. 1967, 32 (4),1212-1215.
Marc Lafrance,; Daniel Shore,; Keith Fagnou. Mild and General Conditions for the Cross-Coupling of Aryl Halides with Pentafluorobenzene and Other Perfluoroaromatics. Org. Lett. 2006, 8(26) ,5097-5100.
Used for the introduction of the pentafluorophenyl group via pentafluorophenyllithium, stable at low temperatures. Review of the effects of the pentafluorophenyl group on reactivity: Fluorine Chem. Rev., 8, 1 (1977).