Perchlorylbenzene

For the benzene derivative with all hydrogen atoms replaced by chlorine atoms, see perchlorobenzene.

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

Perchlorylbenzene

Names
IUPAC name (Trioxo-λ7-chloranyl)benzene
Other names Phenyltrioxo-λ7-chlorane
Identifiers
CAS Number	5390-07-8 N[PubChem]
3D model (JSmol)	Interactive image
PubChem CID	21559072
InChI InChI=1S/C6H5ClO3/c8-7(9,10)6-4-2-1-3-5-6/h1-5H Key: XUEMDHFELUYLBX-UHFFFAOYSA-N
SMILES C1=CC=C(C=C1)Cl(=O)(=O)=O
Properties
Chemical formula	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). Infobox references

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

• Electrophilic aromatic substitution
• Aromatic sulfonation
• Aromatic nitration