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One of several isomers of dichloronitrobenzene, it is a yellow solid that is insoluble in water. It is produced by nitration of 1,4-dichlorobenzene. It is a precursor to many derivatives of commercial interest. Hydrogenation gives 1,4-dichloroaniline.
This reaction affords a mixture of isomers. Using an acid ratio of 30% nitric acid, 56% sulfuric acid and 14% water, the product mix is typically 34-36% 2-nitrochlorobenzene and 63-65% 4-nitrochlorobenzene, with only about 1% 3-nitrochlorobenzene. [1]
The nitration of 1,2-dichlorobenzene mainly produces 1,2-dichloro-4-nitrobenzene, together with smaller amounts of the 3-nitro isomer. It can also be prepared by chlorination of 1-chloro-4-nitrobenzene. [1] One of the chlorides is reactive toward nucleophiles.
Nitrochlorobenzene is typically synthesized by nitration of chlorobenzene in the presence of sulfuric acid: C 6 H 5 Cl + HNO 3 → O 2 NC 6 H 4 Cl + H 2 O. This reaction affords a mixture of isomers. Using an acid ratio of 30/56/14, the product mix is typically 34-36% 2-nitrochlorobenzene and 63-65% 4-nitrochlorobenzene, with only about 1% 3 ...
Nitration gives 2,4-dinitrochlorobenzene, and 3,4-dichloronitrobenzene. Reduction with iron metal gives 4-chloroaniline . The electron-withdrawing nature of the appended nitro-group makes the benzene ring especially susceptible to nucleophilic aromatic substitution , unlike related chlorobenzene.
The phrase ipso nitration was first used by Perrin and Skinner in 1971, in an investigation into chloroanisole nitration. [18] In one protocol, 4-chloro- n -butylbenzene is reacted with sodium nitrite in t -butanol in the presence of 0.5 mol% Pd 2 (dba) 3 , a biarylphosphine ligand and a phase-transfer catalyst to provide 4-nitro- n -butylbenzene.
Other methods afford the compound less efficiently include the chlorination of 1,3-dinitrobenzene, nitration of o-nitrochlorobenzene and the dinitration of chlorobenzene. [3] By virtue of the two nitro substituents, the chloride in DNCB is particularly susceptible to nucleophilic substitution, at least relative to simple chlorobenzene. In this ...
Nitrobenzene is prepared by nitration of benzene with a mixture of concentrated sulfuric acid, water, and nitric acid. This mixture is sometimes called "mixed acid." The production of nitrobenzene is one of the most dangerous processes conducted in the chemical industry because of the exothermicity of the reaction (ΔH = −117 kJ/mol). [5] +