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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 most abundantly produced aryl halide, chlorobenzene, is produced by this route: [4] C 6 H 6 + Cl 2 → C 6 H 5 Cl + HCl. Monochlorination of benzene is accompanied by formation of the dichlorobenzene derivatives. [3] Arenes with electron donating groups react with halogens even in the absence of Lewis acids.
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.
More recently, trifluoromethylation of diazonium salts has been developed and is referred to as a 'Sandmeyer-type' reaction. Diazonium salts also react with boronates, iodide, thiols, water, hypophosphorous acid and others, [6] and fluorination can be carried out using tetrafluoroborate anions (Balz–Schiemann reaction). However, since these ...
Most commonly, diazonium salts are prepared by treatment of aromatic amines with nitrous acid and additional acid. Usually the nitrous acid is generated in situ (in the same flask) from sodium nitrite and the excess mineral acid (usually aqueous HCl, H 2 SO 4, p-H 3 CC 6 H 4 SO 3 H, or H[BF 4]): ArNH 2 + HNO 2 + HX → [ArN 2] + X − + 2 H 2 O
Diazotization of aniline in the presence of hydrochloric acid: C 6 H 5 NH 2 + HNO 2 + HCl → [C 6 H 5 N 2]Cl + 2 H 2 O. The tetrafluoroborate can be obtained from crude benzenediazonium chloride by salt metathesis using tetrafluoroboric acid. [C 6 H 5 N 2]Cl + HBF 4 → [C 6 H 5 N 2]BF 4 + HCl. The tetrafluoroborate is more stable than the ...
The carbylamine reaction (also known as the Hoffmann isocyanide synthesis) is the synthesis of an isocyanide by the reaction of a primary amine, chloroform, and base.The conversion involves the intermediacy of dichlorocarbene.
However, the extent of chlorination is difficult to control. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst. [2] The haloform reaction, using chlorine and sodium hydroxide, is also able to generate alkyl halides from methyl ketones, and related compounds. Chloroform was formerly ...