1,3-Dihydroxynaphthalene

1,3-Naphthalenediol.svg naphthoresorcinol, 1,3-naphthalenediol 132-86-5 correct CAS 381547 8282 205-079-7 8601 5X457YEW8Y 1S/C10H8O2/c11-8-5-7-3-1-2-4-9(7)10(12)6-8/h1-6,11-12H XOOMNEFVDUTJPP-UHFFFAOYSA-N C1=CC=C2C(=C1)C=C(C=C2O)O 10 8 2 colorless or white solid 122–124 07 08 Warning 315 319 335 341 203 261 264 264+265 271 280 302+352 304+340 305+351+338 318 319 321 332+317 337+317 362+364 403+233 405 501 Ethyl phenylacetylmalonate.z 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.Booth Gerald Ullmann's Encyclopedia of Industrial Chemistry Naphthalene Derivatives 2000 10.1002/14356007.a17_009 978-3-527-30385-4 An alternative laboratory route is decarboxylation of 1,3-dihydroxynaphthalene-2-carboxylic acid, which in turn is obtained by cyclization of esters of phenylacetylmalonate.Naphthoresorcinol Organic Syntheses 1945 25 73 10.15227/orgsyn.025.0073 free Karl Meyer, Henry S. Bloch The compound attracted some interest because its conjugate base exists as the dionate tautomer: thumb|left|Tautomerization induced by deprotonation of 1,3-dihydroxynaphthalene. 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.Hand Elli Smakula Horowitz Robert M. The Structure of 1,3-Naphthalenediol Anion The Journal of Organic Chemistry 1964 29 10 3088–3090 10.1021/jo01033a517 Further reading Mukhopadhyay Pritam Iwashita Yuya Shirakawa Michihiro Kawano Shin-Ichiro Fujita Norifumi Shinkai Seiji Spontaneous Colorimetric Sensing of the Positional Isomers of Dihydroxynaphthalene in a 1D Organogel Matrix Angewandte Chemie International Edition 2006 45 10 1592–1595 10.1002/anie.200503158 16470894 References Category:Dihydroxynaphthalene