1,5-Dihydroxynaphthalene

1,5-Dihydroxynaphthalene
Names
	Preferred IUPAC name Naphthalene-1,5-diol
	Other names Azurol; 1,5-Naphthalenediol
Identifiers
CAS Number	83-56-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	6492;
ECHA InfoCard	100.001.353
PubChem CID	6749;
UNII	P25HC23VH6 ;
CompTox Dashboard (EPA)	DTXSID2052574 ;
	InChI 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;
	SMILES c1cc2c(cccc2O)c(c1)O;
Properties
Chemical formula	C10H8O2
Molar mass	160.172 g·mol−1
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 [77 °F], 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 ^[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 (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 (8632): 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.

[EuropeanCommission-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.

[Ullmann-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 (8632): 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. doi:10.1002/anie.200503158. PMID 16470894.

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