1-Naphthylamine is an aromatic amine derived from

naphthalene Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromati ...

. It can cause bladder cancer (transitional cell carcinoma). It crystallizes in colorless needles which melt at 50 °C. It possesses a disagreeable odor,

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s readily, and turns brown on exposure to air. It is the precursor to a variety of dyes..

Preparation and reactions

It can be prepared by reducing 1-nitronaphthalene with iron and hydrochloric acid followed by

steam distillation Steam distillation is a separation process that consists in distilling water together with other volatile and non-volatile components. The steam from the boiling water carries the vapor of the volatiles to a condenser; both are cooled and ret ...

. Oxidizing agents, such as ferric chloride, give a blue precipitate with solutions of its salts. Chromic acid converts it into

1-naphthoquinone Naphthoquinones constitute a class of organic compounds structurally related to naphthalene. Two isomers are common for the parent naphthoquinones: * 1,2-Naphthoquinone * 1,4-Naphthoquinone Natural products * Alkannin * Hexahydroxy-1,4-napht ...

. Sodium in boiling amyl alcohol reduces the unsubstituted ring, giving tetrahydro-1-naphthylamine. This tetrahydro compound yields adipic acid when oxidized by potassium permanganate. At 200 °C in sulfuric acid, it converts to

1-naphthol 1-Naphthol, or α-naphthol, is a fluorescent organic compound with the formula . It is a white solid. It is an isomer of 2-naphthol differing by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues ...

Use in dyes

The sulfonic acid derivatives of 1-naphthylamine are used for the preparation of

azo dye Azo dyes are organic compounds bearing the functional group R−N=N−R′, in which R and R′ are usually aryl and substituted aryl groups. They are a commercially important family of azo compounds, i.e. compounds containing the C-N=N ...

. These compounds possess the important property of dyeing unmordanted cotton. An important derivative is naphthionic acid (1-aminonaphthalene-4-sulfonic acid), which is produced by heating 1-naphthylamine and

sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular formu ...

to 170–180 °C in the presence of crystallized

oxalic acid Oxalic acid is an organic acid with the systematic name ethanedioic acid and formula . It is the simplest dicarboxylic acid. It is a white crystalline solid that forms a colorless solution in water. Its name comes from the fact that early inve ...

. It forms small needles, very sparingly soluble in water. Upon treatment with the bis(diazonium) derivative of benzidine, 1-aminonaphthalene-4-sulfonic acid gives Congo red.

Safety

It is listed as one of the 13 carcinogens covered by the OSHA General Industry Standards.OSHA Standard 1910.1003
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References

{{DEFAULTSORT:Naphthylamine, 1- Naphthylamines IARC Group 3 carcinogens 1-Naphthyl compounds

Preparation and reactions

Use in dyes

Safety

See also

References