1,5-Dihydroxynaphthalene

Chemical compound From Wikipedia, the free encyclopedia

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

Quick facts Names, Identifiers ...
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 Edit this at Wikidata
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 white solid
Melting point 259–261 Â°C (498–502 Â°F; 532–534 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa).
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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]

In supramolecular chemistry, 1,5-dihydroxynaphthalene is a popular reagent.[3][4]

References

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