1,3-Dihydroxynaphthalene

1,3-Dihydroxynaphthalene

Names
Other names naphthoresorcinol, 1,3-naphthalenediol
Identifiers
CAS Number	132-86-5  Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL381547
ChemSpider	8282
ECHA InfoCard	100.004.619
EC Number	205-079-7
PubChem CID	8601
UNII	5X457YEW8Y
CompTox Dashboard (EPA)	DTXSID8059631
InChI 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
SMILES C1=CC=C2C(=C1)C=C(C=C2O)O
Properties
Chemical formula	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:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335, H341
Precautionary statements	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

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.

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

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.