1,5-Dihydroxynaphthalene

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1,5-Dihydroxynaphthalene
Naphthalin-1,5-diol.svg
Names
Preferred IUPAC name
Naphthalene-1,5-diol
Other names
Azurol; 1,5-Naphthalenediol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.353 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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
Appearancewhite 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).

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.

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

  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..
  3. ↑ Li, Qiaowei; Zhang, Wenyu; Miljanić, Ognjen Š.; Sue, Chi-Hau; Zhao, Yan-Li; Liu, Lihua; Knobler, Carolyn B.; Stoddart, J. Fraser; Yaghi, Omar M. (2009). "Docking in Metal-Organic Frameworks". Science. 325 (5942): 855–859. Bibcode:2009Sci...325..855L. doi:10.1126/science.1175441. hdl: 10220/6961 . PMID   19679809. S2CID   12410454.
  4. ↑ Mukhopadhyay, Pritam; Iwashita, Yuya; Shirakawa, Michihiro; Kawano, Shin-Ichiro; Fujita, Norifumi; Shinkai, Seiji (2006). "Spontaneous Colorimetric Sensing of the Positional Isomers of Dihydroxynaphthalene in a 1D Organogel Matrix". Angewandte Chemie International Edition. 45 (10): 1592–1595. Bibcode:2006ACIE...45.1592M. doi:10.1002/anie.200503158. PMID   16470894.
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