1,5-Dihydroxynaphthalene

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

1,5-Dihydroxynaphthalene
Names
Preferred IUPAC name
Naphthalene-1,5-diol
Other names
Azurol; 1,5-Naphthalenediol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.353
UNII
  • 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
  • c1cc2c(cccc2O)c(c1)O
Properties
C10H8O2
Molar mass 160.172 g·mol−1
Appearance Grey to light brown solid[1]
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

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.[2]

References
  1. European Commission. Directorate General for Health & Consumers (2010). Opinion on 1,5-Naphthalenediol : COLIPA n° A18 (PDF). Brussels: European Commission. doi:10.2772/27149. ISBN 978-92-79-12751-9. OCLC 1056423805.
  2. Booth, Gerald (2005). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_009. ISBN 3527306730..
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