Perchlorylbenzene
{{for|the benzene derivative with all hydrogen atoms replaced by chlorine atoms|perchlorobenzene}}{{Chembox
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| ImageFile = Perchlorylbenzene.png
| ImageSize = 100 px
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| IUPACName = (Trioxo-λ7-chloranyl)benzene
| OtherNames = Phenyltrioxo-λ7-chlorane
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| Section1 = {{Chembox Identifiers
| CASNo = 5390-07-8
| CASNo_Ref = {{Cascite|changed|PubChem}}
| PubChem = 21559072
| StdInChI=1S/C6H5ClO3/c8-7(9,10)6-4-2-1-3-5-6/h1-5H
| StdInChIKey = XUEMDHFELUYLBX-UHFFFAOYSA-N
| SMILES = C1=CC=C(C=C1)Cl(=O)(=O)=O
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| Section2 = {{Chembox Properties
| Formula = |C=6|H=5|Cl=1|O=3
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| BoilingPtC = 232
| BoilingPt_notes = (78 °C @ 2 mmHg)
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| Section3 = {{Chembox Hazards
| MainHazards = Explosive
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}}Perchlorylbenzene (C6H5ClO3, PhClO3), is an aromatic compound prepared by direct electrophilic perchlorylation of benzene using perchloryl fluoride and aluminum trichloride:{{Cite journal|last=Inman|first=C. E.|last2=Oesterling|first2=R. E.|last3=Tyczkowski|first3=E. A.|date=1958-10-01|title=Reactions of Perchloryl Fluoride with Organic Compounds. I. Perchlorylation of Aromatic Compounds1|journal=Journal of the American Chemical Society|volume=80|issue=19|pages=5286–5288|doi=10.1021/ja01552a069|issn=0002-7863}}
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.{{Cite book|title=The Preparatory Manual of Explosives|last=Ledgard|first=Jared|publisher=|year=2007|isbn=9780615142906|location=|pages=}}