1,5-Dihydroxynaphthalene

1,5-Dihydroxynaphthalene

Names
IUPAC name Naphthalene-1,5-diol
Other names Azurol; 1,5-Naphthalenediol
Identifiers
CAS Number	83-56-7
3D model (Jmol)	Interactive image
ChemSpider	6492
ECHA InfoCard	100.001.353
PubChem	6749
InChI InChI=1S/C10H8O2/c11-9-5-1-3-7-8(9)4-2-6-10(7)12/h1-6,11-12H Key: BOKGTLAJQHTOKE-UHFFFAOYSA-N InChI=1/C10H8O2/c11-9-5-1-3-7-8(9)4-2-6-10(7)12/h1-6,11-12H Key: BOKGTLAJQHTOKE-UHFFFAOYAJ
SMILES c1cc2c(cccc2O)c(c1)O
Properties
Chemical formula	C10H8O2
Molar mass	160.17 g·mol^−1
Appearance	Colorless solid
Melting point	259–261 °C (498–502 °F; 532–534 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

1,5-Dihydroxynaphthalene is an organic compound with the formula C₁₀H₆(OH)₂. It is one of several isomers of dihydroxynaphthalene. It exists as colorless crystals that are soluble in polar organic solvents. It is a precursor to certain dyes.

Preparation and use

1,5-Dihydroxynaphthalene is prepared from naphthalene-1,5-disulfonic acid by hydrolysis with strong base followed by acidification.

It couples with various aryl diazonium salts to give diazo dyes. Oxidation with chromium trioxide gives juglone, a naturally occurring dye.^[1]

References

1. Gerald Booth "Naphthalene Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_009.