2,3-Dihydroxynaphthalene Chemical Properties

Melting point:

161-165 °C (lit.) 162-164 °C

Boiling point:

246.06°C (rough estimate)

Density 

1.0924 (rough estimate)

vapor pressure 

0.8 hPa (149 °C)

refractive index 

1.5178 (estimate)

Flash point:

175 °C

storage temp. 

Store below +30°C.

solubility 

4g/l

form 

Powder

pka

9.10±0.40(Predicted)

color 

White to pinkish to beige-grayish

PH

6 (1g/l, H2O, 20℃)

Water Solubility 

slightly soluble

BRN 

742375

CAS DataBase Reference

92-44-4(CAS DataBase Reference)

NIST Chemistry Reference

2,3-Naphthalenediol(92-44-4)

EPA Substance Registry System

2,3-Naphthalenediol (92-44-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

RTECS 

QJ4750000

F 

10-23

Autoignition Temperature

>330 °C

TSCA 

Yes

HS Code 

29072900

Toxicity

LD50 orally in Rabbit: 970 mg/kg

MSDS

• Language:English Provider:2,3-Dihydroxynaphthalene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
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2,3-Dihydroxynaphthalene Usage And Synthesis

Chemical Properties

Off white to redish white powder. 2,3-Naphthalenediol [92-44-4], mp 161℃, gives a dark blue color with iron(III) chloride; is aminated to 2- amino-3-naphthol at 140℃ and 2,3-naphthalenediamine at 240℃; and couples with diazotized anilines in the 1- or 1,4-positions.

Uses

2,3-Naphthalenediol is used in cosmetics asa component of oxidative hair dye. It is usedat a concentration of <0.1%.

Uses

2,3-Dihydroxynaphthalene is used in making dyes, pigments, fluorescent whiteners, tanning agents, antioxidants, and antiseptics.

Uses

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

Definition

ChEBI: Naphthalene-2,3-diol is a naphthalenediol.

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.

Health Hazard

2,3-Naphthalenediol shows low toxicity andmild irritant actions on the skin and eyes. Theoral LD50 value for rats of a 5% solutionin propylene glycol may be on the orderof 675 mg/kg (calculated by the method ofWeil). The intravenous LD50 value for miceis 56 mg/kg. At 1% concentration, it causedslight eye irritation in female albino rabbitsand exhibited erythemal response in guineapigs. At the 0.1% level (concentration in hairdye), it had no reaction on human skin. Thiscompound was nonmutagenic in Salmonellatyphimurium strain tests.
There is very little information in the literatureon the toxicity of 2,3-naphthalenediol.Assessment by the CIR expert panel on thesafety of this compound as used in cosmeticshas been inconclusive (Cosmetic, Toiletryand Fragrance Association 1987b).

Synthesis

2,3-Dihydroxynaphthalene is prepared by caustic fusion of 3-hydroxynaphthalene-2,6-disulfonic acid followed by treatment with dilute sulfuric acid under pressure, or by acid desulfonation of 2,3-dihydroxynaphthalene-6-sulfonic acid.

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