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37760

Sigma-Aldrich

2,3-Dihydroxynaphthalene

≥98.0% (HPLC)

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Synonym(s):
2,3-Naphthalenediol
Linear Formula:
C10H6(OH)2
CAS Number:
Molecular Weight:
160.17
Beilstein/REAXYS Number:
742375
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥98.0% (HPLC)

sublimation residue

≤1%

mp

161-165 °C (lit.)
162-164 °C

SMILES string

Oc1cc2ccccc2cc1O

InChI

1S/C10H8O2/c11-9-5-7-3-1-2-4-8(7)6-10(9)12/h1-6,11-12H

InChI key

JRNGUTKWMSBIBF-UHFFFAOYSA-N

Gene Information

human ... BAD(572)

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1 of 4

This Item
N6250D116408374733
2,3-Dihydroxynaphthalene ≥98.0% (HPLC)

37760

2,3-Dihydroxynaphthalene

1,3-Dihydroxynaphthalene ≥99%, crystalline

N6250

1,3-Dihydroxynaphthalene

2,7-Dihydroxynaphthalene 97%

D116408

2,7-Dihydroxynaphthalene

2,6-Diisopropylaniline 97%

374733

2,6-Diisopropylaniline

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

mp

161-165 °C (lit.), 162-164 °C

mp

123-125 °C (lit.), 124-125 °C

mp

185-190 °C (lit.)

mp

−45 °C (lit.)

sublimation residue

≤1%

sublimation residue

-

sublimation residue

-

sublimation residue

-

Gene Information

human ... BAD(572)

Gene Information

-

Gene Information

-

Gene Information

-

General description

2,3-Dihydroxynaphthalene is a polyhydroxy phenol. It is an aromatic dihydroxy compound having hydroxyl groups at ortho positions. Its reaction with molybdenum(VI) complexes has been reported. The asymmetric oxidative coupling polymerization of 2,3-dihydroxynaphthalene using the Cu(I)-bisoxazoline complex as catalyst has been reported to afford poly(2,3-dihydroxy-1,4-naphthylene), having a continuous 1,1′-bi-2-naphthol main chain structure. The nitrodisplacement reaction between nitrophthalodinitriles and 2,3-dihydroxynaphthalene has been investigated.

Application

2,3-Dihydroxynaphthalene may be used in the following studies:
  • Construction of dinaphtho[2,1-b;2′,3′-d]furan-6-ol, via dehydration reaction in the presence of strong acid.
  • As fused ring catecholate type ligand for the surface modification of nanocrystalline TiO2 particles.
  • As adsorptive and competing ligand during the chemical speciation of iron in seawater by cathodic stripping voltammetry.
  • Synthesis of cyclotriphosphazene derivatives, used as non-halogen flame retardants

pictograms

CorrosionExclamation mark

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

347.0 °F

flash_point_c

175 °C

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Copper (I)-catalyzed asymmetric oxidative coupling polymerization of 2, 3-dihydroxynaphthalene using bisoxazoline ligands.
Habaue S, et al.
Macromolecules, 36(8), 2604-2608 (2003)
Application of cyclophosphazene derivatives as flame retardants for ABS.
Shin YJ, et al.
Journal of Industrial and Engineering Chemistry (Amsterdam, Netherlands), 16(3), 364-367 (2010)
Tatjana D Savić et al.
Nanoscale, 4(5), 1612-1619 (2012-02-09)
Surface modification of nanocrystalline TiO(2) particles (45 Å) with catecholate-type ligands consisting of an extended aromatic ring system, i.e., 2,3-dihydroxynaphthalene and anthrarobin, was found to alter the optical properties of the nanoparticles in a similar way to modification with catechol.
Synthesis of bis (ether anhydride) s for poly (ether imide) s having 1, 2-linked units by nitrodisplacement with catechol derivatives.
Eastmond GC and Paprotny J.
Macromolecules, 28(7), 2140-2146 (1995)
Constant M G van den Berg
Analytical chemistry, 78(1), 156-163 (2005-12-31)
The chemical speciation of iron in seawater is determined by cathodic stripping voltammetry using 2,3-dihydroxynaphthalene (DHN) as adsorptive and competing ligand. The optimized conditions include a DHN concentration of 0.5-1 microM, seawater at its original pH of 8, and equilibration

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