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1,3-Dihydroxynaphthalene

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1,3-Dihydroxynaphthalene
1,3-Naphthalenediol.svg
Names
Other names
naphthoresorcinol, 1,3-naphthalenediol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.619 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 205-079-7
PubChem CID
UNII
  • InChI=1S/C10H8O2/c11-8-5-7-3-1-2-4-9(7)10(12)6-8/h1-6,11-12H
    Key: XOOMNEFVDUTJPP-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)C=C(C=C2O)O
Properties
C10H8O2
Molar mass 160.172 g·mol−1
Appearancecolorless or white solid
Melting point 122–124 °C (252–255 °F; 395–397 K)
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
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).

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:

Tautomerization induced by deprotonation of 1,3-dihydroxynaphthalene. 1,3naphthdiol.svg
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. [3]

Further reading

References

  1. ↑ Booth, Gerald (2000). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a17_009. ISBN   978-3-527-30385-4.
  2. ↑ Karl Meyer, Henry S. Bloch (1945). "Naphthoresorcinol". Organic Syntheses. 25: 73. doi:10.15227/orgsyn.025.0073.
  3. ↑ 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.
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