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1,4-Dihydroxynaphthalene

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1,4-Dihydroxynaphthalene
1,4-Naphthalenediol.svg
Names
Other names
  • 1,4-Naphthoquinol
  • 1,4-naphthalenediol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • 209-336-4
KEGG
PubChem CID
UNII
  • InChI=1S/C10H8O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6,11-12H
    Key: PCILLCXFKWDRMK-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)C(=CC=C2O)O
Properties
C10H8O2
Molar mass 160.172 g·mol−1
Appearancewhite solid
Melting point 190 °C (374 °F; 463 K) tautomerizes
Acidity (pKa)pKa1 = 9.37 (26.5 °C)
pKa2 = 10.93 (26.5 °C)
Hazards
GHS labelling: [1]
GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Danger
H302, H315, H318, H335, H412
P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,4-Dihydroxynaphthalene is an organic compound with the formula C10H6(OH)2. It is one of several isomers of dihydroxynaphthalene. The compound attracted some interest because in its molten state, it exists mainly as the diketo tautomer. [2]

tautomerization of 1,4-dihydroxynaphthalene 1,4-naphthdiol.svg
tautomerization of 1,4-dihydroxynaphthalene

It can be prepared by reduction of 1,4-naphthoquinone with dithionite as well as by acid-hydrolysis of 1-hydroxy-4-aminonaphthalene. Both routes are reversible: oxidation of the diol give the naphthoquinone and addition of ammonia gives back the hydroxyaminonaphthalene. [3]

Further reading

References

  1. ↑ PubChem. "1,4-Naphthalenediol". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-02-02.
  2. ↑ Pearson, Myrna S.; Jensky, Barbara J.; Greer, Francis X.; Hagstrom, Janice P.; Wells, Nancy M. (1978). "Substituent effects in the keto-enol tautomerism of fused 1,4-naphthalenediols". The Journal of Organic Chemistry. 43 (24): 4617–4622. doi:10.1021/jo00418a017.
  3. ↑ Booth, Gerald (2000). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a17_009. ISBN   978-3-527-30385-4.
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