1,5-Dihydroxynaphthalene

1,5-Dihydroxynaphthalene

1,5-Dihydroxynaphthalene

Chemical compound

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 ...

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. [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. [2]
    Booth, Gerald (2005). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_009. ISBN 3527306730..
  3. [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. [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. doi:10.1002/anie.200503158. PMID 16470894.
Share this article:

This article uses material from the Wikipedia article 1,5-Dihydroxynaphthalene, and is written by contributors. Text is available under a CC BY-SA 4.0 International License; additional terms may apply. Images, videos and audio are available under their respective licenses.