Aniline

aniline dyeaniline dyescoal tar dyeAniline hydrochlorideanilinesanilinium aromatic amineanilideaniline blackaniline salt
Aniline is an organic compound with the formula C 6 H 5 NH 2.wikipedia
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Amine

aminoaminesamino group
Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine.
Important amines include amino acids, biogenic amines, trimethylamine, and aniline; see for a list of amines.

Aromatic amine

aromatic aminesaromaticPrimary Aromatic Amine
Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine.
It is a broad class of compounds that encompasses anilines, but also many more complex aromatic rings and many amine substituents beyond NH 2.

Nitrobenzene

nitrobenzenesnitroarenesNO 2
First, benzene is nitrated with a concentrated mixture of nitric acid and sulfuric acid at 50 to 60 °C to yield nitrobenzene.
It is produced on a large scale from benzene as a precursor to aniline.

Antoine Béchamp

A. Béchamp
The reduction of nitrobenzene to aniline was also performed as part of reductions by Antoine Béchamp in 1854, using iron as the reductant (Bechamp reduction).
Béchamp developed the Béchamp reduction, an inexpensive method to produce aniline dye, permitting Perkin to launch the synthetic-dye industry.

Hydrogenation

hydrogenatedcatalytic hydrogenationhydrogenated vegetable oil
The nitrobenzene is then hydrogenated (typically at 200–300 °C) in the presence of metal catalysts:
The reduction of nitrobenzene to aniline has been reported to be catalysed by fullerene, its mono-anion, atmospheric hydrogen and UV light.

Benzene

benzene ringbenzolbenzene rings
First, benzene is nitrated with a concentrated mixture of nitric acid and sulfuric acid at 50 to 60 °C to yield nitrobenzene.
Examples of simple benzene derivatives are phenol, toluene, and aniline, abbreviated PhOH, PhMe, and PhNH 2, respectively.

Toluidine

p''-toluidinepara-toluidinep-toluidine
In commerce, three brands of aniline are distinguished: aniline oil for blue, which is pure aniline; aniline oil for red, a mixture of equimolecular quantities of aniline and ortho- and para-toluidines; and aniline oil for safranine, which contains aniline and ortho-toluidine and is obtained from the distillate (échappés) of the fuchsine fusion. These include toluidines, xylidines, chloroanilines, aminobenzoic acids, nitroanilines, and many others.
All three are aryl amines whose chemical structures are similar to aniline except that a methyl group is substituted onto the benzene ring.

Nitroaniline

These include toluidines, xylidines, chloroanilines, aminobenzoic acids, nitroanilines, and many others.
The term nitroaniline in chemistry refers to a derivative of aniline (C 6 H 5 NH 2 ) containing a nitro group (—NO 2 ) There are three simple nitroanilines of formula C 6 H 4 (NH 2 )(NO 2 ) which differ only in the position of the nitro group:

Bechamp reduction

Béchamp reduction
The reduction of nitrobenzene to aniline was also performed as part of reductions by Antoine Béchamp in 1854, using iron as the reductant (Bechamp reduction).
The Bechamp reduction is used to reduce aromatic nitro compounds to their corresponding anilines, using iron and hydrochloric acid.

Phenol

carbolic acidphenoxidephenolate
Aniline can alternatively be prepared from ammonia and phenol derived from the cumene process.
However, phenol's ring is so strongly activated—second only to aniline—that bromination or chlorination of phenol leads to substitution on all carbon atoms ortho and para to the hydroxy group, not only on one carbon.

Diphenylamine

Hypochlorous acid gives 4-aminophenol and para-amino diphenylamine.
The compound is a derivative of aniline, consisting of an amine bound to two phenyl groups.

1,4-Benzoquinone

benzoquinonep-benzoquinonequinhydrone
Chromic acid converts it into quinone, whereas chlorates, in the presence of certain metallic salts (especially of vanadium), give aniline black.
Quinone was originally prepared industrially by oxidation of aniline, for example by manganese dioxide.

4-Bromoaniline

p-bromoaniline
The reaction to form 4-bromoaniline is to protect the amine with acetyl chloride, then hydrolyse back to reform aniline.
4-Bromoaniline is a compound where an aniline molecule is substituted with a bromine atom on the para position.

Polyaniline

aniline blackaniline-blackPANI
Chromic acid converts it into quinone, whereas chlorates, in the presence of certain metallic salts (especially of vanadium), give aniline black.

Acetanilide

acetanilidacetanilidesAntifebrin
The amides formed from aniline are sometimes called anilides, for example CH 3 -CO-NH-C 6 H 5 is acetanilide.
Acetanilide can be produced by reacting acetic anhydride with aniline:

Dimethylaniline

N,N-DimethylanilineN'',''N''-DimethylanilineDimethylaniline (DMA)
N-Methylation of aniline with methanol at elevated temperatures over acid catalysts gives N-methylaniline and dimethylaniline:
N,N-Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of aniline.

Nitric acid

nitricHNO 3 aqua fortis
First, benzene is nitrated with a concentrated mixture of nitric acid and sulfuric acid at 50 to 60 °C to yield nitrobenzene.
The nitro group can be reduced to give an amine group, allowing synthesis of aniline compounds from various nitrobenzenes:

Sulfanilic acid

sulphanilic acid
For example, reaction of aniline with sulfuric acid at 180 °C produces sulfanilic acid, H 2 NC 6 H 4 SO 3 H.
Sulfanilic acid can be produced by sulfonation of aniline:

N-Methylaniline

N''-methylanilinemono methyl anilineMonomethyl aniline
N-Methylation of aniline with methanol at elevated temperatures over acid catalysts gives N-methylaniline and dimethylaniline:
N-Methylaniline (NMA) is an aniline derivative.

Nitration

nitratednitratingaromatic nitration
First, benzene is nitrated with a concentrated mixture of nitric acid and sulfuric acid at 50 to 60 °C to yield nitrobenzene.
The direct nitration of aniline with nitric acid and sulfuric acid, according to one source, results in a 50/50 mixture of para- and meta-nitroaniline isomers.

2,4,6-Tribromoaniline

If bromine water is added to aniline, the bromine water is decolourised and a white precipitate of 2,4,6-tribromoaniline is formed.
2,4,6-Tribromoaniline can be prepared by treating bromine water with aniline in a solution of acetic acid or dilute hydrochloric acid:

Enamine

Its high reactivity reflects that it is an enamine, which enhances the electron-donating ability of the ring.
This usually will rearrange to the imine; however there are several exceptions (such as aniline).

Diazonium compound

diazonium saltdiazotizationdiazonium
Aniline and its ring-substituted derivatives react with nitrous acid to form diazonium salts.
For example, the dye called aniline yellow is produced by mixing aniline and cold solution of diazonium salt and then shaking it vigorously.

Phenazine

Phenazineseurhodinphenazine dye
It reacts with nitrobenzene to produce phenazine in the Wohl-Aue reaction.

Anilide

phenylamidephenylamidesβ-ketoanilide
The amides formed from aniline are sometimes called anilides, for example CH 3 -CO-NH-C 6 H 5 is acetanilide.
Anilides (or phenylamides) are a class of chemical compounds which are acyl derivatives of aniline.