1,3-Dihydroxynaphthalene
| Names | |
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| Other names
naphthoresorcinol, 1,3-naphthalenediol
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.004.619 |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C10H8O2 | |
| Molar mass | 160.172 g·mol−1 |
| Appearance | colorless or white solid |
| Melting point | 122–124 °C (252–255 °F; 395–397 K) |
| Hazards | |
| GHS labelling:[1] | |
| Warning | |
| H315, H319, H335, H341 | |
| P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501 | |
| Flash point | Ethyl phenylacetylmalonate.z |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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1,3-Dihydroxynaphthalene is an organic compound with the formula C10H6(OH)2. It is one of several isomers of dihydroxynaphthalene.
It can be prepared by hydrolysis of 1,3-diaminonaphthalene.[1] An alternative laboratory route is decarboxylation of 1,3-dihydroxynaphthalene-2-carboxylic acid, which in turn is obtained by cyclization of esters of phenylacetylmalonate.[2]
The compound attracted some interest because its conjugate base exists as the dionate tautomer:
The pKa of 1,3-dihydroxynaphthalene is 7.35, which is anomalous compared to the pKa's of phenol and 1-naphthol, which are respectively 9.95 and 9.85. This anomaly is explained by the tautomerism.[3]
Further reading
- 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.
References
- ^ Booth, Gerald (2000). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a17_009. ISBN 978-3-527-30385-4.
- ^ Karl Meyer, Henry S. Bloch (1945). "Naphthoresorcinol". Organic Syntheses. 25: 73. doi:10.15227/orgsyn.025.0073.
- ^ Hand, Elli Smakula; Horowitz, Robert M. (1964). "The Structure of 1,3-Naphthalenediol Anion". The Journal of Organic Chemistry. 29 (10): 3088–3090. doi:10.1021/jo01033a517.