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For example, reaction of aniline with sulfuric acid at 180 °C produces sulfanilic acid, H 2 NC 6 H 4 SO 3 H. If bromine water is added to aniline, the bromine water is decolourised and a white precipitate of 2,4,6-tribromoaniline is formed. To generate the mono-substituted product, a protection with acetyl chloride is required:
Aniline is a benzenoid compound. The NH 2 group attached to the benzene ring means that there is a lone pair of electrons that can enter into conjugation with the benzene ring resulting in delocalization in the aniline. Aniline absorbs in the K (220 - 250 nm) and the B (250 - 290 nm) bands exhibited by benzenoid compounds.
2,4,6-Trichloroaniline can be prepared by reaction of dry aniline with chlorine gas while in an anhydrous solution of carbon tetrachloride. 2,4,6-Trichloroaniline precipitates from solution as a white solid. In the presence of water in the solution the white material will be contaminated with aniline black. [3]
In the industrial production, MDA is produced by reaction of formaldehyde and aniline in the presence of hydrochloric acid. [3] MDA is a common monomer in the synthesis of polymer materials. These include polyamides, [4] polyimides and polyimines. [5] MDA is also used extensively as a precursor to methylene diphenyl diisocyanate (MDI).
General structure of an imine. Schiff bases are imines in which R 3 is an alkyl or aryl group (not a hydrogen). R 1 and R 2 may be hydrogens General structure of an azomethine compound. In organic chemistry, a Schiff base (named after Hugo Schiff) is a compound with the general structure R 1 R 2 C=NR 3 (R 3 = alkyl or aryl, but not hydrogen).
2,4,6-Tribromoaniline is a brominated derivative of aniline with the formula C 6 H 4 Br 3 N. It is used in organic synthesis of pharmaceuticals, agrochemicals and fire-extinguishing agents. It is used in organic synthesis of pharmaceuticals, agrochemicals and fire-extinguishing agents.
N,N-Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of aniline. It is a tertiary amine, featuring a dimethylamino group attached to a phenyl group. This oily liquid is colourless when pure, but commercial samples are often yellow. It is an important precursor to dyes such as crystal violet.
2-Nitroaniline is prepared commercially by the reaction of 2-nitrochlorobenzene with ammonia: [2] ClC 6 H 4 NO 2 + 2 NH 3 → H 2 NC 6 H 4 NO 2 + NH 4 Cl. Many other methods exist for the synthesis of this compound. Direct nitration of aniline is inefficient since anilinium is produced instead.