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2,3-Dihydroxynaphthalene
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Name

2,3-Dihydroxynaphthalene

 EINECS 202-156-7
CAS No. 92-44-4 Density 1.33 g/cm3
PSA 40.46000 LogP 2.25100
Solubility slightly soluble in water Melting Point 161-165 °C(lit.)
Formula C10H8O2 Boiling Point 353.9 °C at 760 mmHg
Molecular Weight 160.172 Flash Point 181 °C
Transport Information N/A Appearance Off white to redish white powder
Safety 26-37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 92-44-4 (2,3-Dihydroxynaphthalene) Hazard Symbols IrritantXi
Synonyms

2,3-Naphthalenediol;NSC 8707;Naphthalene-2,3-diol;

Article Data 32

2,3-Dihydroxynaphthalene Synthetic route

C14H16O4

92-44-4

2,3-naphthalenediol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In neat (no solvent, solid phase) at 20℃; for 0.583333h; Green chemistry;95%

3,4-dihydro-2H-naphtho[2,3-b]1,4-dioxepine

92-44-4

2,3-naphthalenediol

Conditions
ConditionsYield
With aluminum (III) chloride In benzene for 5h; Reflux;92%
91-20-3

naphthalene

92-44-4

2,3-naphthalenediol

Conditions
ConditionsYield
With 2,4,6-trimethylphenylcarbene copper; dihydrogen peroxide; trimethyldodecylammonium chloride In octane at 50℃; for 7h; Reagent/catalyst;83.8%
Multi-step reaction with 2 steps
1.1: boron tribromide / hexane / 60 h / 120 °C / Sealed tube
1.2: 0.03 h / 0 °C / Schlenk technique
2.1: 3-chloro-benzenecarboperoxoic acid / water; ethanol / 6 h / 0 - 20 °C
View Scheme
10103-06-7

2,3-dimethoxynaphthalene

A

18515-11-2

3-methoxy-2-naphthol

B

92-44-4

2,3-naphthalenediol

Conditions
ConditionsYield
With orcinol; Acetobacterium dehalogenans veratrol-O-demethylase; Desulfitobacterium hafniense methyltransferase dhaf4611 In aq. buffer at 35℃; for 24h; pH=6.5; Inert atmosphere; Enzymatic reaction; regioselective reaction;A 81%
B 19%
33933-59-4

3-tert-butoxy-2-hydroxynaphthalene

A

116310-13-5

6-tert-butyl-2,3-dihydroxynaphthalene

B

92-44-4

2,3-naphthalenediol

Conditions
ConditionsYield
With sulfuric acid In n-heptane; dichloromethane at 20℃; for 2h;A 76.7%
B n/a
269-43-2

naphtho<2,3-d>-1,3-dioxole

92-44-4

2,3-naphthalenediol

Conditions
ConditionsYield
With aluminum tri-bromide In ethanethiol at 0℃; for 0.5h;73%
With aluminum tri-bromide In ethanethiol at 0℃; for 0.5h;73%

C26H20O4*2C10H8O2

A

99-94-5

p-Toluic acid

B

92-44-4

2,3-naphthalenediol

C

2-hydroxy-3-naphthyl p-methylbenzoate

D

C26H20O4

Conditions
ConditionsYield
With sodium carbonate at 145℃; for 5h;A 19%
B 67%
C 46%
D 14%
5656-49-5

2,2-dimethylnaphtho[2,3-d]-1,3-dioxole

92-44-4

2,3-naphthalenediol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 2h;60%
58692-14-1

syn-1,2:3,4-naphthalene dioxide

92-44-4

2,3-naphthalenediol

Conditions
ConditionsYield
In xylene at 190℃; for 24h;50%
56-23-5

tetrachloromethane

148-75-4

2-naphthol-3,6-disulphonic acid

92-44-4

2,3-naphthalenediol

Conditions
ConditionsYield
beim Schmelzen; Erwaermen des entstehenden 2.3-Dioxy-naphthalin-sulfonsaeure-(6) auf 280-320grad;

2,3-Dihydroxynaphthalene Consensus Reports

Reported in EPA TSCA Inventory.

2,3-Dihydroxynaphthalene Specification

The 2,3-Dihydroxynaphthalene, with the CAS registry number 92-44-4, is also known as 2,3-Naphthalenediol. It belongs to the product categories of Aromatics; Naphthalene derivatives. Its EINECS number is 202-156-7. This chemical's molecular formula is C10H8O2 and molecular weight is 160.17. What's more, its systematic name is naphthalene-2,3-diol. It should be sealed and stored in a cool and dry place. Moreover, it should be protected from light. It is used in organic synthesis and dye manufacture.

Physical properties of 2,3-Dihydroxynaphthalene are: (1)ACD/LogP: 2.11; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.11; (4)ACD/LogD (pH 7.4): 2.1; (5)ACD/BCF (pH 5.5): 23.66; (6)ACD/BCF (pH 7.4): 23.2; (7)ACD/KOC (pH 5.5): 335.05; (8)ACD/KOC (pH 7.4): 328.55; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 18.46 Å2; (13)Index of Refraction: 1.725; (14)Molar Refractivity: 47.85 cm3; (15)Molar Volume: 120.4 cm3; (16)Polarizability: 18.97×10-24cm3; (17)Surface Tension: 64.4 dyne/cm; (18)Density: 1.33 g/cm3; (19)Flash Point: 181 °C; (20)Enthalpy of Vaporization: 62.25 kJ/mol; (21)Boiling Point: 353.9 °C at 760 mmHg; (22)Vapour Pressure: 1.71E-05 mmHg at 25°C.

Preparation: this chemical can be prepared by naphtho[2,3-d][1,3]dioxole at the temperature of 0 °C. This reaction will need reagent AlBr3 and solvent C2H5SH with the reaction time of 30 min. The yield is about 73%.

2,3-Dihydroxynaphthalene can be prepared by naphtho[2,3-d][1,3]dioxole at the temperature of 0 °C

Uses of 2,3-Dihydroxynaphthalene: it can be used to produce dinaphtho[2,3-b;2',3'-e][1,4]dioxin-5,14-dione at the temperature of 100 °C. It will need reagent pyridine with the reaction time of 6 hours. The yield is about 87%.

2,3-Dihydroxynaphthalene can be used to produce dinaphtho[2,3-b;2',3'-e][1,4]dioxin-5,14-dione at the temperature of 100 °C

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing and gloves.

You can still convert the following datas into molecular structure:
(1)SMILES: Oc2cc1c(cccc1)cc2O
(2)Std. InChI: InChI=1S/C10H8O2/c11-9-5-7-3-1-2-4-8(7)6-10(9)12/h1-6,11-12H
(3)Std. InChIKey: JRNGUTKWMSBIBF-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 56mg/kg (56mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03884.

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