2,3-Dihydroxynaphthalene supplier

Name
2,3-Dihydroxynaphthalene
EINECS 202-156-7
CAS No. 92-44-4
Article Data32
CAS DataBase
Density 1.33 g/cm³
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
Appearance Off white to redish white powder
Safety 26-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2,3-Naphthalenediol;NSC 8707;Naphthalene-2,3-diol;
PSA 40.46000
LogP 2.25100

Synthetic route

: C14H16O4

: 92-44-4
2,3-naphthalenediol

Conditions

Conditions	Yield
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

Conditions	Yield
With aluminum (III) chloride In benzene for 5h; Reflux;	92%

: 91-20-3
naphthalene

: 92-44-4
2,3-naphthalenediol

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

...Expand

: 5656-49-5
2,2-dimethylnaphtho[2,3-d]-1,3-dioxole

: 92-44-4
2,3-naphthalenediol

Conditions

Conditions	Yield
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

Conditions	Yield
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

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

: 17454-47-6
2,3-naphtho-15-crown-5

A: 91-20-3
naphthalene

B: 135-19-3
β-naphthol

C: 92-44-4
2,3-naphthalenediol

Conditions

Conditions	Yield
In tetrahydrofuran for 0.25h; selectivity of reductive cleavage of the aryl-oxygen bonds; also for other arenocrown ethers;

...Expand

: 22426-46-6
2,3-naphthalenediol-2,3-diacetate

: 92-44-4
2,3-naphthalenediol

Conditions

Conditions	Yield
With lipase of Pseudomonas sp; water In various solvent(s) at 25℃; for 14h; Hydrolysis; deacetylation;
With lipase from Candida rugosa; cholate functionalized DOPC vesicles In aq. buffer for 24h; Enzymatic reaction;

sodium salt of/the/ 2.3-dioxy-naphthalene-sulfonic acid-(6): sodium salt of/the/ 2.3-dioxy-naphthalene-sulfonic acid-(6)

A: 258-81-1
Dinaphtho[2,3-b;2',3'-e][1,4]dioxin

B: 92-44-4
2,3-naphthalenediol

Conditions

Conditions	Yield
With sulfuric acid

2.3-dihydroxy-naphthalene-sulfonic acid-(6): 2.3-dihydroxy-naphthalene-sulfonic acid-(6)

: 92-44-4
2,3-naphthalenediol

Conditions

Conditions	Yield
With sulfuric acid at 150 - 160℃;

2.3-dioxy-naphthalene-6-sulfonate sodium: 2.3-dioxy-naphthalene-6-sulfonate sodium

: 92-44-4
2,3-naphthalenediol

Conditions

Conditions	Yield
With sulfuric acid at 180 - 190℃;
at 200℃;
With sodium hydroxide at 300 - 320℃;
at 200℃;
at 230 - 240℃;

2-oxy-3-amino-naphthalene-sulfonic acid-(7): 2-oxy-3-amino-naphthalene-sulfonic acid-(7)

: 92-44-4
2,3-naphthalenediol

Conditions

Conditions	Yield
With sulfuric acid at 180℃;

2-oxy-naphthalene-3.6-disulfonate sodium: 2-oxy-naphthalene-3.6-disulfonate sodium

: 92-44-4
2,3-naphthalenediol

Conditions

Conditions	Yield
With sodium hydroxide at 300 - 320℃;

: 6399-72-0
6-amino-7-hydroxy-2-naphthalenesulphonic acid

diluted mineral acid: diluted mineral acid

: 92-44-4
2,3-naphthalenediol

Conditions

Conditions	Yield
at 180 - 200℃;

: 52864-96-7
1,4-Dibromo-2,3-dihydroxynaphthalene

SnCl2: SnCl2

: 92-44-4
2,3-naphthalenediol

: 672919-94-7
6,7,8-trihydroxy-[1]naphthoic acid

: 10034-85-2
hydrogen iodide

A: 105284-13-7
6,7-dihydroxy-[1]naphthoic acid

B: 135-19-3
β-naphthol

C: 92-44-4
2,3-naphthalenediol

...Expand

: C16H10Cl2O3

: 92-44-4
2,3-naphthalenediol

Conditions

Conditions	Yield
Conversion of starting material;

: 1344113-51-4
C18H26O2Si

: 92-44-4
2,3-naphthalenediol

Conditions

Conditions	Yield
Stage #1: C18H26O2Si With palladium(II) trimethylacetate; [bis(acetoxy)iodo]benzene In α,α,α-trifluorotoluene at 120℃; Inert atmosphere; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; Stage #3: With water In tetrahydrofuran

: 135-19-3
β-naphthol

: 92-44-4
2,3-naphthalenediol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1H-imidazole / tetrahydrofuran / 20 °C / Inert atmosphere 1.3: 20 °C 2.1: palladium(II) trimethylacetate; [bis(acetoxy)iodo]benzene / α,α,α-trifluorotoluene / 120 °C / Inert atmosphere 2.2: 20 °C View Scheme

: 438250-13-6
naphthalene-2,3-diyl dihexanoate

: 92-44-4
2,3-naphthalenediol

Conditions

Conditions	Yield
With lipase from Candida rugosa; cholate functionalized DOPC vesicles In aq. buffer for 24h; Enzymatic reaction;

: 3-hydroxynaphthalene-2-yl β-L-glucoside

: 92-44-4
2,3-naphthalenediol

Conditions

Conditions	Yield
With β-glucosidase from almond; cholate functionalized DOPC vesicles In aq. buffer for 24h; Enzymatic reaction;

: C16H10B2Cl2O2

A: 3428-24-8
4,5-dichlorocatechol

B: 92-44-4
2,3-naphthalenediol

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In ethanol; water at 0 - 20℃; for 6h; Overall yield = 0.02 g;

: 77-78-1
dimethyl sulfate

: 92-44-4
2,3-naphthalenediol

: 10103-06-7
2,3-dimethoxynaphthalene

Conditions

Conditions	Yield
With sodium hydroxide; triisooctyl amine In dichloromethane; water at 0℃; for 10h;	100%
With sodium hydroxide In dichloromethane; water at 0℃; for 10h;	100%
With potassium carbonate In acetone for 15h; Heating;	94%

: 92-44-4
2,3-naphthalenediol

: 791-28-6
Triphenylphosphine oxide

: (2,3-naphthalenedioxy)triphenylphosphorane

Conditions

Conditions	Yield
at 100 - 110℃; for 2h;	100%

: 75-36-5
acetyl chloride

: 92-44-4
2,3-naphthalenediol

poly(2,3-diacetoxy-1,4-naphthylene), product of asymmetric oxidative coupling polymerization and acetylation, methanol-insoluble part, Mn 6.2E3 Da, Mw/Mn 2.3 by SEC; monomer(s): 2,3-dihydroxynaphthalene; acetyl chloride: poly(2,3-diacetoxy-1,4-naphthylene), product of asymmetric oxidative coupling polymerization and acetylation, methanol-insoluble part, Mn 6.2E3 Da, Mw/Mn 2.3 by SEC; monomer(s): 2,3-dihydroxynaphthalene; acetyl chloride

Conditions

Conditions	Yield
Stage #1: 2,3-naphthalenediol With oxygen; (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline); copper(l) chloride In tetrahydrofuran at 20℃; for 48h; Stage #2: acetyl chloride With pyridine In dichloromethane for 12h;	100%

: 75-36-5
acetyl chloride

: 92-44-4
2,3-naphthalenediol

poly(2,3-diacetoxy-1,4-naphthylene), product of asymmetric oxidative coupling polymerization and acetylation, methanol-insoluble part, Mn 6.9E3 Da, Mw/Mn 1.5 by SEC; monomer(s): 2,3-dihydroxynaphthalene; acetyl chloride: poly(2,3-diacetoxy-1,4-naphthylene), product of asymmetric oxidative coupling polymerization and acetylation, methanol-insoluble part, Mn 6.9E3 Da, Mw/Mn 1.5 by SEC; monomer(s): 2,3-dihydroxynaphthalene; acetyl chloride

Conditions

Conditions	Yield
Stage #1: 2,3-naphthalenediol With oxygen; (S,S)-2,2'-methylenebis(4-phenyl-2-oxazoline); copper(l) chloride In tetrahydrofuran at 20℃; for 24h; Stage #2: acetyl chloride With pyridine In dichloromethane for 12h;	100%

: 7440-74-6
indium

: 92-44-4
2,3-naphthalenediol

: 121581-68-8, 121581-73-5
In{OC10H6(OH)-2,3}

Conditions

Conditions	Yield
With Et4NClO4 In acetonitrile byproducts: H2; Electrolysis; using indium metall anode, platinum wire cathode in soln. of Et4NClO4 and dihydroxynaphthalene (2 h, N2, 20 mA), hydrogen gas evolving at the cathode and forming product at the anode; product collected by filtration, washed with acetonitrile and Et2O, dried (vac.); elem. anal.;	100%

: 121-43-7
Trimethyl borate

: 92-44-4
2,3-naphthalenediol

: 19812-60-3
tetraethylene glycol monoacrylate

: CH2CHC(O)(OCH2CH2)4O(BO2C10H6)

Conditions

Conditions	Yield
In acetonitrile naphthalene diol reacted with soln. of B(OCH3)3 at 60°C for 1 h; tetraethylene glycol monoacrylate added, stirred for 2 h; cooled; solvent evapd. at 40°C for 24 h;	100%

...Expand

: tetrakis(dimethylamido)titanium(IV)

: 92-44-4
2,3-naphthalenediol

: bis(dimethylamido)naphthalene-2,3-diolato-titanium(IV)

Conditions

Conditions	Yield
In pentane at 20℃; for 19h; Schlenk technique; Glovebox; Inert atmosphere;	100%

: 31643-49-9
4-Nitrophthalonitrile

: 92-44-4
2,3-naphthalenediol

: 161204-26-8
2,3-bis-(3,4-dicyanophenoxy)naphthalene

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide for 24h; Ambient temperature;	99.22%

: 31643-49-9
4-Nitrophthalonitrile

: 92-44-4
2,3-naphthalenediol

A tetranitrile: tetranitrile

B: 161204-26-8
2,3-bis-(3,4-dicyanophenoxy)naphthalene

Conditions

Conditions	Yield
With potassium carbonate In methanol; dimethyl sulfoxide	A 99.2% B n/a

...Expand

: 124-63-0
methanesulfonyl chloride

: 92-44-4
2,3-naphthalenediol

: 22426-45-5
2,3-bis(methylsulfonyloxy)naphthalene

Conditions

Conditions	Yield
With triethylamine In chloroform at 0℃;	99%
With triethylamine In dichloromethane for 2h; Product distribution / selectivity;	96%
With triethylamine In ethyl acetate at 0 - 20℃; for 0.166667h; Green chemistry;	88%

: 92-44-4
2,3-naphthalenediol

: Cinchonine

: C20H12BO4(1-)*C19H22N2O*H(1+)

Conditions

Conditions	Yield
With boric acid In acetone	99%

: 874-60-2
4-methyl-benzoyl chloride

: 92-44-4
2,3-naphthalenediol

: C26H20O4

Conditions

Conditions	Yield
at 120℃; for 0.25h;	99%

: 11113-50-1
boric acid

: 92-44-4
2,3-naphthalenediol

: 1071759-34-6
cinchonidine

: cinchonidinium (bis-2,3-naphthalenediyl)orthoborate salt

Conditions

Conditions	Yield
In acetone mixt. of alkaloid, boric acid and 2,3-dihydroxynaphthalene (molar ratio 1:1:2) dissolved in hot acetone, warmed; evapd., noncryst. solid product;	99%

...Expand

: PhP(Se)Se(Se)PPh(OC10H6O-2,3)

: 92-44-4
2,3-naphthalenediol

: 1228931-21-2
PhP(Se)(OC10H6O-2,3)

Conditions

Conditions	Yield
In toluene for 7h; Reflux;	99%

: 2551-83-9
allyltrimethoxysilane

: 75-59-2
tetramethyl ammoniumhydroxide

: 92-44-4
2,3-naphthalenediol

: tetramethylammonium bis(2,3-naphthalenediolato)allylsiliconate

Conditions

Conditions	Yield
In methanol at -20℃; for 0.25h; Inert atmosphere;	99%

...Expand

: 62-53-3
aniline

2,3-naphthalenediol: 2,3-naphthalenediol

: 1-phenylazo-2,3-dihydroxynaphthalene

Conditions

Conditions	Yield
Stage #1: aniline With hydrogenchloride; sodium nitrite In water for 0.5h; Stage #2: 2,3-naphthalenediol In water for 0.5h;	99%

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.

Product Name

2,3-Dihydroxynaphthalene

Synthetic route

2,3-Dihydroxynaphthalene Consensus Reports

2,3-Dihydroxynaphthalene Specification

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