Structure via PubChem · Public domain (PubChem)
2-naphthol
Sign in to saveAlso known as beta-naphthol, 2-naphthalenol, beta-hydroxynaphthalene, Isonaphthol, beta-Naphthyl alcohol, beta-Monoxynaphthalene, 2-Naphtol
2-Naphthol, or β-naphthol, is a fluorescent colorless (or occasionally yellow) crystalline solid with the formula C10H7OH. It is an isomer of 1-naphthol, differing by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol, but more reactive. Both isomers are soluble in simple alcohols, ethers, and chloroform. 2-Naphthol is a widely used intermediate for the production of dyes and other compounds.
Chemical data
- Formula
- C10H8O
- Molecular weight
- 144.17 g/mol
- IUPAC name
- naphthalen-2-ol
- SMILES
- C1=CC=C2C=C(C=CC2=C1)O
- InChIKey
- JWAZRIHNYRIHIV-UHFFFAOYSA-N
- XLogP
- 2.7
- Polar surface area
- 20.2 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 144.058
Show 8 more facts
- boiling point
- 295
- chemical formula
- C₁₀H₈O
- flash point
- 153
- Commons category
- 2-Naphthol
- canonical SMILES
- C1=CC=C2C=C(C=CC2=C1)O
- density
- 1.217
- melting point
- 123
- ionization energy
- 7.85
via Wikidata · CC0
~2 min read
Article
6 sectionsContents
- Production
- 2-Naphthol-derived dyes
- Reactions
- Safety
- References
- External links
2-Naphthol, or β-naphthol, is a fluorescent colorless (or occasionally yellow) crystalline solid with the formula C10H7OH. It is an isomer of 1-naphthol, differing by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol, but more reactive. Both isomers are soluble in simple alcohols, ethers, and chloroform. 2-Naphthol is a widely used intermediate for the production of dyes and other compounds.
==Production== Traditionally, 2-naphthol is produced by a two-step process that begins with the sulfonation of naphthalene in sulfuric acid: C10H8 + H2SO4 → C10H7SO3H + H2O The sulfonic acid group is then cleaved in molten sodium hydroxide: C10H7(SO3H) + 3 NaOH → C10H7ONa + Na2SO3 + 2 H2O Neutralization of the product with acid gives 2-naphthol.