351-83-7

white to off-white fluffy crystalline powder

4-Fluoroacetanilide solutions and commercial samples serve as the crystallizing material in metastable zone width (MZW) measurements in aqueous ethanol[3].

4-Fluoroacetanilide is prepared from commercial 4-fluoroaniline and acetic anhydride, affording a yellow solid (19%) with a melting point of 150 °C[1]. The 13C-labelled analogue, 1-[13C]-4-fluoroacetanilide, is synthesized by reacting 4-fluoroaniline directly with acetyl-1-[13C]-chloride in a 1:1.1 molar ratio, then washing with distilled water and recrystallizing from ethanol[2].

[1]Bienvenu, A., Barthelemy, A., Boichut, S., Marquet, B., Billard, T., & Langlois, B. R. (2002). Synthesis of 4-Fluorophenols from 4-tert-Butylphenols and Fluoride Sources Under Oxidative Conditions. Collection of Czechoslovak Chemical Communications, 67(10), 1467–1478. https://doi.org/10.1135/cccc20021467
[2]SCARFE, G. B. (1999). Studies on the metabolism of 4-fluoroaniline and 4-fluoroacetanilide in rat: formation of 4-acetamidophenol (paracetamol) and its metabolites via defluorination and N-acetylation. Xenobiotica, 29(2), 205–216. https://doi.org/10.1080/004982599238759
[3]Threlfall, T. L., De'Ath, R. W., & Coles, S. J. (2013). Metastable Zone Widths, Conformational Multiplicity, and Seeding. Organic Process Research & Development, 17(3), 578–584. https://doi.org/10.1021/op3003486