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Preferred IUPAC name Naphthalene-1,5-diol | |
Other names Azurol; 1,5-Naphthalenediol | |
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3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.001.353 |
PubChem CID | |
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CompTox Dashboard (EPA) | |
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Properties | |
Chemical formula | C10H8O2 |
Molar mass | 160.172 g·mol |
Appearance | white 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 , 100 kPa). Infobox references |
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 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.
In supramolecular chemistry, 1,5-dihydroxynaphthalene is a popular reagent.
References
- 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.
- 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; 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.
- 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.