2-Naphthylamine

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2-Naphthylamine
Image:2-Naphthylamine.PNG
IUPAC name	2-Aminonaphthalene
Other names	2-Naphthylamine ß-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 It is a known human carcinogen and has largely been replaced by less toxic compounds. 2-Naphthylamine is prepared by heating 2-naphthol with ammonium zinc chloride to 200-210 °C; or in the form of its acetyl derivative by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.

Role in disease

2-Naphthylamine is found in cigarette smoke and suspected to be contributory to the development of bladder cancer.^[1]

References

See also

• Naphthalene
• Naphthol
• 1-Naphthylamine

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Acknowledgement and Attribution Regarding Sources of Content

Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .