Perchlorylbenzene (C6H5ClO3, PhClO3, is an aromatic compound prepared by direct electrophilic perchlorylation of benzene using perchloryl fluoride and aluminum trichloride:[1]
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| Names | |
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| IUPAC name
(Trioxo-λ7-chloranyl)benzene
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| Other names
Phenyltrioxo-λ7-chlorane
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| 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
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Explosive |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
editReferences
edit- ^ 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.