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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.
The main steps in this process are the production of chlorobenzene from benzene, hydrochloric acid and oxygen, and the subsequent hydrolysis of chlorobenzene to phenol. [4] The first step uses either a copper or iron chloride catalyst and exposes the materials to air at 200–250 °C.
For example, 2,4-dinitrochlorobenzene reacts in basic solution to give a phenol. Unlike in most other substitution reactions, fluoride is the best leaving group, and iodide the worst. [ 16 ] A 2018 paper indicates that this situation may actually be rather common, occurring in systems that were previously assumed to proceed via S N Ar mechanisms.
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]
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.
Phenol is also a versatile precursor to a large collection of drugs, most notably aspirin but also many herbicides and pharmaceutical drugs. Phenol is a component in liquid–liquid phenol–chloroform extraction technique used in molecular biology for obtaining nucleic acids from tissues or cell culture samples.
Aniline: 184.3 3.69 –5.96 –5.87 ... Phenol: 181.75 3.60 43.0 –7.27 K f [2] K b [1] Water: ... Chlorobenzene: 131.7 [15] p-chlorobenzotrifluoride: 1.34
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]