Chemistry:1,5-Dihydroxynaphthalene
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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
- ↑ European Commission. Directorate General for Health & Consumers (2010). Opinion on 1,5-Naphthalenediol : COLIPA n° A18.. Brussels: European Commission. doi:10.2772/27149. ISBN 978-92-79-12751-9. OCLC 1056423805. https://ec.europa.eu/health/scientific_committees/consumer_safety/docs/sccs_o_033.pdf.
- ↑ Booth, Gerald (2005). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_009. ISBN 3527306730..
- ↑ Li, Qiaowei; Zhang, Wenyu; Miljanić, Ognjen Š.; Sue, Chi-Hau; Zhao, Yan-Li; Liu, Lihua; Knobler, Carolyn B.; Stoddart, J. Fraser et al. (2009). "Docking in Metal-Organic Frameworks". Science 325 (5942): 855–859. doi:10.1126/science.1175441. PMID 19679809. Bibcode: 2009Sci...325..855L.
- ↑ 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. Bibcode: 2006ACIE...45.1592M.
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