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2-Naphthylamine

2-Naphthylamine

IUPAC name	2-Aminonaphthalene
Other names	2-Naphthylamine β-Naphthylamine
Identifiers
CAS number	91-59-8
SMILES	NC2=CC1=CC=CC=C1C=C2
Properties
Molecular formula	C₁₀H₉N
Molar mass	143.19 g/mol
Density	1.061 g/cm³
Melting point	111-113 °C
Boiling point	306 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

2-Naphthylamine is an aromatic amine. It is used to make azo dyes. It is a known human carcinogen and has largely been replaced by less toxic compounds. 2-Naphthylamine is prepared by heating 2-naphthol with ammonium zinc chloride to 200-210 °C; or in the form of its acetyl derivative by heating 2-naphthol with ammonium acetate to 270-280 °C. It forms odorless, colorless plates which melt at 111-112 °C. It gives no color with ferric chloride. When reduced by sodium in boiling amyl alcohol solution it forms alicyclic tetrahydro-3-naphthylamine, which has most of the properties of the aliphatic amines; it is strongly alkaline in reaction, has an ammoniacal odor and cannot be diazotized. On oxidation it yields ortho-carboxy-hydrocinnamic acid, HO₂C•C₆H₄•CH₂•CH₂•CO₂H. Numerous sulfonic acids derived from 2-naphthylamine are known. Of these, the δ-acid and Bronner's acid are of more value technically, since they combine with ortho-tetrazoditolyl to produce fine red dye-stuffs.