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Perchlorylbenzene

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For the benzene derivative with all hydrogen atoms replaced by chlorine atoms, see perchlorobenzene.
Perchlorylbenzene
Names
IUPAC name (Trioxo-λ-chloranyl)benzene
Other names Phenyltrioxo-λ-chlorane
Identifiers
CAS Number
3D model (JSmol)
PubChem CID
InChI
  • InChI=1S/C6H5ClO3/c8-7(9,10)6-4-2-1-3-5-6/h1-5HKey: XUEMDHFELUYLBX-UHFFFAOYSA-N
SMILES
  • C1=CC=C(C=C1)Cl(=O)(=O)=O
Properties
Chemical formula C6H5ClO3
Molar mass 160.55 g·mol
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 , 100 kPa). Infobox references
Chemical compound

Perchlorylbenzene (C6H5ClO3, PhClO3, 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 (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.

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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