Perchlorylbenzene (C6H5ClO3, PhClO3, systematic name: phenyltrioxo-λ7-chlorane) is an aromatic compound prepared by direct electrophilic perchlorylation of benzene using perchloryl fluoride and aluminum trichloride:
Ph-H + F-ClO3 + AlCl3 → Ph-ClO3 + HCl + AlCl2F (93% yield, based on AlCl3)
The compound is described as a somewhat shock-sensitive oily liquid (b.p. 232 °C @ 760 mmHg, 78 °C @ 2 mmHg). It exhibits low chemical reactivity and is inert towards acidic (HCl (aq.)) or reducing (LiAlH4, H2/Pd) conditions. However, it undergoes hydrolysis upon reflux in aqueous KOH:
Ph-ClO3 + KOH → Ph-OH + KClO3
It and its derivatives have been investigated as novel energetic materials analogous to nitro compounds.
References
Perchlorylbenzene Wikipedia(Text) CC BY-SA