1,5-Dihydroxynaphthalene

From Wikipedia, the free encyclopedia
Jump to: navigation, search
1,5-Dihydroxynaphthalene
1,5-Naphthalenediol.png
Names
IUPAC name
Naphthalene-1,5-diol
Other names
Azurol; 1,5-Naphthalenediol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.353
Properties
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[edit]

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[edit]

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