37760

Sigma-Aldrich

2,3-Dihydroxynaphthalene

≥98.0% (HPLC)

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
Pricing and availability is not currently available.

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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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

Packaging

50, 250 g in poly bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xi

Risk Statement

36/37/38

Safety Statement

26

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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)
Copper (I)-catalyzed asymmetric oxidative coupling polymerization of 2, 3-dihydroxynaphthalene using bisoxazoline ligands.
Habaue S, et al.
Macromolecules, 36(8), 2604-2608 (2003)
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)
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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