Perchlorylbenzene (C<sub>6</sub>H<sub>5</sub>ClO<sub>3</sub>, PhClO<sub>3</sub>), is an aromatic compound prepared by direct electrophilic perchlorylation of benzene using perchloryl fluoride and aluminum trichloride:
The compound is described as a somewhat shock-sensitive oily liquid. It exhibits low chemical reactivity and is inert towards acidic (HCl (aq.)) or reducing (LiAlH<sub>4</sub>, H<sub>2</sub>/Pd) conditions. However, it undergoes hydrolysis upon reflux in aqueous KOH to afford phenol, and undergoes aromatic nitration to afford the meta-nitration product, as expected for a strongly âÂÂI, âÂÂM substituent.
It and its derivatives have been investigated as novel energetic materials analogous to nitro compounds.