Perchlorylbenzene

{{for|the benzene derivative with all hydrogen atoms replaced by chlorine atoms|perchlorobenzene}}{{Chembox

| Name =

| ImageFile = Perchlorylbenzene.png

| ImageSize = 100 px

| ImageAlt =

| IUPACName = (Trioxo-λ⁷-chloranyl)benzene

| OtherNames = Phenyltrioxo-λ⁷-chlorane

| SystematicName =

| 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

}}

| Section2 = {{Chembox Properties

| Formula = |C=6|H=5|Cl=1|O=3

| MolarMass =

| Appearance =

| Density =

| MeltingPtC =

| MeltingPt_notes =

| BoilingPtC = 232

| BoilingPt_notes = (78 °C @ 2 mmHg)

| Solubility =

| SolubleOther = }}

| Section3 = {{Chembox Hazards

| MainHazards = Explosive

| FlashPt =

| AutoignitionPt = }}

| Section4 =

| Section5 =

| Section6 =

}}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}}

File: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.{{Cite book|title=The Preparatory Manual of Explosives|last=Ledgard|first=Jared|publisher=|year=2007|isbn=9780615142906|location=|pages=}}