Perchlorylbenzene

Last updated
Perchlorylbenzene
Perchlorylbenzene.png
Names
IUPAC name
(Trioxo-λ7-chloranyl)benzene
Other names
Phenyltrioxo-λ7-chlorane
Identifiers
3D model (JSmol)
PubChem CID
  • InChI=1S/C6H5ClO3/c8-7(9,10)6-4-2-1-3-5-6/h1-5H
    Key: XUEMDHFELUYLBX-UHFFFAOYSA-N
  • C1=CC=C(C=C1)Cl(=O)(=O)=O
Properties
C6H5ClO3
Molar mass 160.55 g·mol−1
Boiling point 232 °C (450 °F; 505 K) (78 °C @ 2 mmHg)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Explosive
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Perchlorylbenzene (C6H5ClO3, PhClO3), is an aromatic compound prepared by direct electrophilic perchlorylation of benzene using perchloryl fluoride and aluminum trichloride: [1]

Synth-PhClO3.png

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 (LiAlH4, H2/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 –I, –M substituent.

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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