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Perchlorylbenzene (C6H5ClO3, PhClO3), is an 
The compound is described as a somewhat shock-sensitive oily liquid. It exhibits low chemical reactivity and is inert towards acidic (
aromatic compound
Aromatic compounds or arenes are organic compounds "with a chemistry typified by benzene" and "cyclically conjugated."
The word "aromatic" originates from the past grouping of molecules based on odor, before their general chemical properties were ...
prepared by direct electrophilic
In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively charged, have an atom that carr ...
perchlorylation of benzene
Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...
using perchloryl fluoride
Perchloryl fluoride is a reactive gas with the chemical formula . It has a characteristic sweet odor that resembles gasoline and kerosene. It is toxic and is a powerful oxidizing and fluorinating agent. It is the acid fluoride of perchloric acid ...
and aluminum trichloride:
The compound is described as a somewhat shock-sensitive oily liquid. It exhibits low chemical reactivity and is inert towards acidic (HCl HCL may refer to:
Science and medicine
* Hairy cell leukemia, an uncommon and slowly progressing B cell leukemia
* Harvard Cyclotron Laboratory, from 1961 to 2002, a proton accelerator used for research and development
* Hollow-cathode lamp, a s ...
(aq.)) or reducing ( LiAlH4, H2/Pd) conditions. However, it undergoes hydrolysis upon reflux in aqueous KOH to afford phenol
Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire.
The molecule consists of a phenyl group () ...
, and undergoes aromatic nitration
In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group () into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters () between Alcohol ...
to afford the ''meta''-nitration product, as expected for a strongly –''I'', –''M'' substituent.
It and its derivatives have been investigated as novel energetic material
Energetic materials are a class of material with high amount of stored chemical energy that can be released.
Typical classes of energetic materials are e.g. explosives, pyrotechnic compositions, propellants (e.g. smokeless gunpowders and rocket fu ...
s analogous to nitro compound
In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups (). The nitro group is one of the most common explosophores (functional group that makes a compound explosive) used globally. The nit ...
s.
See also
*Electrophilic aromatic substitution
Electrophilic aromatic substitution (SEAr) is an organic reaction in which an atom that is attached to an aromatic ring, aromatic system (usually hydrogen) is replaced by an electrophile. Some of the most important electrophilic aromatic substitut ...
* Aromatic sulfonation
In organic chemistry, aromatic sulfonation is a reaction in which a hydrogen atom on an arene is replaced by a sulfonic acid () group. Together with nitration and chlorination, aromatic sulfonation is a widely used electrophilic aromatic substi ...
* Aromatic nitration
In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group () into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters () between alcohol ...
References
{{Reflist Perchloryl compounds Phenyl compounds