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7-Fluoro-1-tetralone was prepared from 3-(4-fluorobenzoyl)-propionic acid by Wolff-Kishner reduction followed by ring closure with polyphosphoric acid and other substituted 1-tetralones where commercially available. Reduction of 3-(4-fluorobenzoyl)propionic acid with an excess of tert-butylamine borane (TBAB) in the presence of AlCl3 provided 4-(4-fluorophenyl)-1-butanol (87) in 63% yield for the synthesis of LM-1507 sodium salt. Penfluridol 1-[4,4-bis(4-fluorophenyl)butyl]-4-(4-chloro-3-trifluoromethylphenyl)- 4-hydroxypiperidine, C 28 H 27 ClF 5 NO, M r 523.99, mp 105 - 107°C, is obtained by reducing the ketone of 3-(4-fluorobenzoyl)propionic acid into a lactone.
Lodewyk J. Mienie,; Jacobus J. Bergh,; Jeffrey R. Bloomquist,; Neal Castagnoli Jr.,; Stefanus J. Steyn,; Cornelis J. Van der Schyf. p-Fluorophenylglycine in the urine of baboons treated with HPTP, the tetrahydropyridine analog of haloperidol. Life Sciences. 1999, 65 (5), 535-542.
Hyeon Soo Kim,; Minseok Song,; Sanatombi Yumkham,; Jang Hyun Choi,; Taehoon Lee,; Joseph Kwon,; Sung Jae Lee. Identification of a new functional target of haloperidol metabolite: implications for a receptor-independent role of 3-(4-fluorobenzoyl) propionic acid. Journal of Neurochemistry. 2006, 99(2), 458-469.
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P280g-P305+P351+P338
Wear protective gloves. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.