Perchlorylbenzene

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:[1]

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.[2]

See also

References

  1. ↑ Inman, C. E.; Oesterling, R. E.; Tyczkowski, E. A. (1958-10-01). "Reactions of Perchloryl Fluoride with Organic Compounds. I. Perchlorylation of Aromatic Compounds1". Journal of the American Chemical Society. 80 (19): 5286–5288. doi:10.1021/ja01552a069. ISSN 0002-7863.
  2. ↑ Ledgard, Jared (2007). The Preparatory Manual of Explosives. ISBN 9780615142906.
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