1,4-Dihydroxynaphthalene

1,4-Dihydroxynaphthalene
Names
	Other names 1,4-Naphthoquinol; 1,4-naphthalenediol;
Identifiers
CAS Number	571-60-8;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:34063;
ChEMBL	ChEMBL206816;
ChemSpider	10830;
ECHA InfoCard	100.008.489
EC Number	209-336-4;
KEGG	C14785;
PubChem CID	11305;
UNII	AML1P6T42C;
CompTox Dashboard (EPA)	DTXSID5060350 ;
	InChI 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;
	SMILES C1=CC=C2C(=C1)C(=CC=C2O)O;
Properties
Chemical formula	C10H8O2
Molar mass	160.172 g·mol−1
Appearance	white 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:
Pictograms
Signal word	Danger
Hazard statements	H302, H315, H318, H335, H412
Precautionary statements	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). Infobox references

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]

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]

References

^ PubChem. "1,4-Naphthalenediol". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-02-02.
^ 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.
^ Booth, Gerald (2000). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a17_009. ISBN 978-3-527-30385-4.

[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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Further reading

References