Structure via PubChem · Public domain (PubChem)
2-naphthylamine
Sign in to saveAlso known as beta-naphthylamine, 2-aminonaphthalene, BNA, 6-naphthylamine
2-Naphthylamine or 2-aminonaphthalene 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 oxidation. It was formerly used to make azo dyes, but it is a known carcinogen and has largely been replaced by less toxic compounds.
Chemical data
- Formula
- C10H9N
- Molecular weight
- 143.18 g/mol
- IUPAC name
- naphthalen-2-amine
- SMILES
- C1=CC=C2C=C(C=CC2=C1)N
- InChIKey
- JBIJLHTVPXGSAM-UHFFFAOYSA-N
- XLogP
- 2.3
- Polar surface area
- 26 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
1,791 papers- 2-naphthylamine toxicity.Medycyna pracy · 2020
- Dephenylation of the rubber chemical N-phenyl-2-naphthylamine to carcinogenic 2-naphthylamine: a classical problem revisited.Critical reviews in toxicology · 2007
- 2-Naphthylamine.Report on carcinogens : carcinogen profiles · 2004
- 2-Naphthylamine.Report on carcinogens : carcinogen profiles · 2011
- 2-Naphthylamine.Report on carcinogens : carcinogen profiles · 2002
via PubMed
Wikidata facts
- Mass
- 143.073
Show 11 more facts
- chemical formula
- C₁₀H₉N
- ionization energy
- 9.71
- NIOSH Pocket Guide ID
- 0442
- density
- 1.06
- melting point
- 232
- boiling point
- 583
- vapor pressure
- 1
- flash point
- 315
- ceiling exposure limit
- 0
- canonical SMILES
- C1=CC=C2C=C(C=CC2=C1)N
- Commons category
- 2-Naphthylamine
Sources (3)
via Wikidata · CC0
~2 min read
Article
5 sectionsContents
- Preparation
- Reactions
- Role in disease
- See also
- References
2-Naphthylamine or 2-aminonaphthalene 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 oxidation. It was formerly used to make azo dyes, but it is a known carcinogen and has largely been replaced by less toxic compounds.
==Preparation== 2-Naphthylamine is prepared by heating 2-naphthol with ammonium zinc chloride to 200-210 °C, the Bucherer reaction. Its acetyl derivative can be obtained by heating 2-naphthol with ammonium acetate to 270-280 °C.