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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.
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).
Gefahrenhinweise (EU): H225-H302
Highly flammable liquid and vapour. Harmful if swallowed.
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves and eye/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Dispose of contents/container in accordance with local/regional/national/international regulations.