2-Naphthylamine

2-Naphthylamine

Names
Preferred IUPAC name Naphthalen-2-amine
Other names (Naphthalen-2-yl)amine 2-Naphthylamine β-Naphthylamine
Identifiers
CAS Number	91-59-8 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:27878 Y
ChEMBL	ChEMBL278164 Y
ChemSpider	6790 Y
ECHA InfoCard	100.001.892
KEGG	C02227 Y
InChI InChI=1S/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2 Y Key: JBIJLHTVPXGSAM-UHFFFAOYSA-N Y InChI=1/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2 Key: JBIJLHTVPXGSAM-UHFFFAOYAA
SMILES c12ccccc1ccc(N)c2
Properties
Chemical formula	C10H9N
Molar mass	143.19 g·mol−1
Appearance	White to red crystals
Odor	odorless
Density	1.061 g/cm3
Melting point	111 to 113 °C (232 to 235 °F; 384 to 386 K)
Boiling point	306 °C (583 °F; 579 K)
Solubility in water	miscible in hot water
Vapor pressure	1 mmHg (107° C)
Acidity (pKa)	3.92
Magnetic susceptibility (χ)	-98.00·10−6 cm3/mol
Hazards
Flash point	157 °C; 315 °F; 430 K
Related compounds
Related compounds	2-Naphthol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

2-Naphthylamine is one of two isomeric aminonaphthalenes, compounds with the formula C₁₀H₇NH₂. It is a colorless solid, but samples take on a reddish color in air because of oxidiation. The aromatic amine used to be used to make azo dyes. It is a known carcinogen and has largely been replaced by less toxic compounds.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, the Bucherer reaction. It also can be produced its acetyl derivative by heating 2-naphthol with ammonium acetate to 270-280 °C.

It gives no color with iron(III) chloride. When reduced by sodium in boiling amyl alcohol solution, it forms tetrahydro-3-naphthylamine, which exhibits the properties of the aliphatic amines in that it is strongly alkaline in reaction, has an ammoniacal odor and cannot be diazotized.

On oxidation, it yields ortho-carboxy-hydrocinnamic acid, HO₂CC₆H₄CH₂CH₂CO₂H.

Numerous sulfonic acid derivatives of 2-naphthylamine are used in commerce, such as precursors to dyes. Owing to the carcinogenicity of the amine, these derivatives are mainly prepared by amination of the corresponding naphthols. Of them, the δ-acid and Bronner's acid are of more value technically, since they combine with ortho-tetrazoditolyl to produce fine red dye-stuffs.