Perchlorylbenzene

Perchlorylbenzene
Names
	IUPAC name (Trioxo-λ7-chloranyl)benzene
	Other names Phenyltrioxo-λ7-chlorane
Identifiers
CAS Number	5390-07-8 [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

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

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]

References

^ 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.
^ Ledgard, Jared (2007). The Preparatory Manual of Explosives. ISBN 9780615142906.

[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.

[1]

[2]

See also

References