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Chlorobenzene (abbreviated PhCl) is an aryl chloride and the simplest of the chlorobenzenes, consisting of a benzene ring substituted with one chlorine atom. Its chemical formula is C 6 H 5 Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.
[6] [7] Due to the two step nature, the Raschig–Hooker process can be used to produce either chlorobenzene or phenol. Reaction scheme of the Raschig-Hooker process. The Raschig–Hooker process's ability to make phenol makes it comparable to other methods, such as the Dow and Bayer process, which also converts benzene into phenol. In fact ...
Aniline (from Portuguese anil 'indigo shrub', and -ine indicating a derived substance) [6] is an organic compound with the formula C 6 H 5 NH 2. Consisting of a phenyl group ( −C 6 H 5 ) attached to an amino group ( −NH 2 ), aniline is the simplest aromatic amine .
To form 4-chlorophenyl azide specifically, an aniline with a chloride group in the para position is used. The sodium nitrite reacts with aniline to form a diazonium salt that performs nucleophilic substitution with the azide ion formed by another reaction between sodium nitrite and hydrazine hydrate in an acidic medium. Such a reaction takes ...
Instead, the main product he isolated was chlorobenzene. [5] In modern times, the Sandmeyer reaction refers to any method for substitution of an aromatic amino group via preparation of its diazonium salt followed by its displacement with a nucleophile in the presence of catalytic copper(I) salts.
Benzene can be easily converted to chlorobenzene by nucleophilic aromatic substitution via a benzyne intermediate. [1] It is treated with aqueous sodium hydroxide at 350 °C and 300 bar or molten sodium hydroxide at 350 °C to convert it to sodium phenoxide, which yields phenol upon acidification. [2]
One major but discontinued application was the use of chlorobenzene as a solvent for dispersing the herbicide Lasso. Overall, production of aryl chlorides (also naphthyl derivatives) has been declining since the 1980s, in part due to environmental concerns. [3] Triphenylphosphine is produced from chlorobenzene:
Another use of 4-nitrochlorobenzene is its condensation with aniline to produce 4-nitrodiphenylamine. Reductive alkylation of the nitro group affords secondary aryl amines, which are useful antioxidants for rubber. 4-Nitrochlorobenzene is the precursor to the anti-leprosy drug Dapsone (4-[(4-aminobenzene)sulfonyl]aniline). [2]