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Sigma-Aldrich

2,3-Dihydroxynaphthalene

≥98.0% (HPLC)

Synonym(s):

2,3-Naphthalenediol

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About This Item

Linear Formula:
C10H6(OH)2
CAS Number:
92-44-4
Molecular Weight:
160.17
Beilstein/REAXYS Number:
742375
EC Number:
202-156-7
MDL number:
MFCD00004073
UNSPSC Code:
12352100
PubChem Substance ID:
57649747
NACRES:
NA.22

Quality Level

200

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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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
GHS05,GHS07

signalword

Danger

hcodes

H302,H318

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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.
Kentaro Nakanishi et al.
The Journal of organic chemistry, 79(6), 2625-2631 (2014-02-26)
The construction of dinaphtho[2,1-b;2',3'-d]furan-6-ol was developed via a dehydration reaction involving two molecules of 2,3-dihydroxynaphthalene in the presence of a strong acid. Starting from the dinaphthofuran, a variety of butterfly shaped derivatives were synthesized. The optical properties of these compounds
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