92-44-4

Basic information

• Product Name: 2,3-Dihydroxynaphthalene
• Synonyms: 2,3-Dihydroxynapthalene;Naphthalene-2,3-diol;Naphthalenediol-(2,3);2,3-DIHYDROXYNAPHTHALENE;2,3-NAPHTHALENEDIOL;2,3-DIHYDROXYNAPHTHALENE, SUBL.;2 3-DIHYDROXYNAPHTHALENE 98%;2,3-DihydroxylNaphthalene
• CAS NO: 92-44-4
• Molecular Formula: C₁₀H₈O₂
• Molecular Weight: 160.17
• EINECS: 202-156-7
• Product Categories: Aromatics;Naphthalene derivatives;Bioactive Small Molecules;Building Blocks;Cell Biology;Chemical Synthesis;DIG-DY;Organic Building Blocks;Oxygen Compounds;Polyols
• Mol File: 92-44-4.mol
• Article Data: 20

Chemical Properties

• Melting Point: 161-165 °C(lit.)
• Boiling Point: 246.06°C (rough estimate)
• Flash Point: 175 °C
• Appearance: White to pinkish to beige-grayish/Powder
• Density: 1.0924 (rough estimate)
• Vapor Pressure: 1.71E-05mmHg at 25°C
• Refractive Index: 1.5178 (estimate)
• Storage Temp.: 2-8°C
• Solubility: 4g/l
• PKA: 9.10±0.40(Predicted)
• Water Solubility: slightly soluble
• BRN: 742375
• CAS DataBase Reference: 2,3-Dihydroxynaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dihydroxynaphthalene(92-44-4)
• EPA Substance Registry System: 2,3-Dihydroxynaphthalene(92-44-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: QJ4750000
• F: 10-23
• TSCA: Yes
• Hazardous Substances Data: 92-44-4(Hazardous Substances Data)

Usage

Chemical Properties

Off white to redish white powder

Uses

Different sources of media describe the Uses of 92-44-4 differently. You can refer to the following data:
1. 2,3-Naphthalenediol is used in cosmetics asa component of oxidative hair dye. It is usedat a concentration of <0.1%.
2. 2,3-Dihydroxynaphthalene is used in making dyes, pigments, fluorescent whiteners, tanning agents, antioxidants, and antiseptics.
3. 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

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).

InChI:InChI=1/C10H8O2/c11-9-5-7-3-1-2-4-8(7)6-10(9)12/h1-6,11-12H

Synthetic route

C14H16O4 → 2,3-naphthalenediol (92-44-4)

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 → 2,3-naphthalenediol (92-44-4)

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

naphthalene (91-20-3) → 2,3-naphthalenediol (92-44-4)

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

2,3-dimethoxynaphthalene (10103-06-7) → 3-methoxy-2-naphthol (18515-11-2) + 2,3-naphthalenediol (92-44-4)

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%

3-tert-butoxy-2-hydroxynaphthalene (33933-59-4) → 6-tert-butyl-2,3-dihydroxynaphthalene (116310-13-5) + 2,3-naphthalenediol (92-44-4)

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

naphtho<2,3-d>-1,3-dioxole (269-43-2) → 2,3-naphthalenediol (92-44-4)

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 → p-Toluic acid (99-94-5) + 2,3-naphthalenediol (92-44-4) + 2-hydroxy-3-naphthyl p-methylbenzoate + C26H20O4

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

2,2-dimethylnaphtho[2,3-d]-1,3-dioxole (5656-49-5) → 2,3-naphthalenediol (92-44-4)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 2h;	60%

syn-1,2:3,4-naphthalene dioxide (58692-14-1) → 2,3-naphthalenediol (92-44-4)

Conditions	Yield
In xylene at 190℃; for 24h;	50%

tetrachloromethane (56-23-5) + 2-naphthol-3,6-disulphonic acid (148-75-4) → 2,3-naphthalenediol (92-44-4)

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

2,3-naphtho-15-crown-5 (17454-47-6) → naphthalene (91-20-3) + β-naphthol (135-19-3) + 2,3-naphthalenediol (92-44-4)

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

2,3-naphthalenediol-2,3-diacetate (22426-46-6) → 2,3-naphthalenediol (92-44-4)

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) → Dinaphtho[2,3-b;2',3'-e][1,4]dioxin (258-81-1) + 2,3-naphthalenediol (92-44-4)

Conditions	Yield
With sulfuric acid

2.3-dihydroxy-naphthalene-sulfonic acid-(6) → 2,3-naphthalenediol (92-44-4)

Conditions	Yield
With sulfuric acid at 150 - 160℃;

2.3-dioxy-naphthalene-6-sulfonate sodium → 2,3-naphthalenediol (92-44-4)

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) → 2,3-naphthalenediol (92-44-4)

Conditions	Yield
With sulfuric acid at 180℃;

2-oxy-naphthalene-3.6-disulfonate sodium → 2,3-naphthalenediol (92-44-4)

Conditions	Yield
With sodium hydroxide at 300 - 320℃;

6-amino-7-hydroxy-2-naphthalenesulphonic acid (6399-72-0) + diluted mineral acid → 2,3-naphthalenediol (92-44-4)

Conditions	Yield
at 180 - 200℃;

1,4-Dibromo-2,3-dihydroxynaphthalene (52864-96-7) + SnCl2 → 2,3-naphthalenediol (92-44-4)

6,7,8-trihydroxy-[1]naphthoic acid (672919-94-7) + hydrogen iodide (10034-85-2) → 6,7-dihydroxy-[1]naphthoic acid (105284-13-7) + β-naphthol (135-19-3) + 2,3-naphthalenediol (92-44-4)

C16H10Cl2O3 → 2,3-naphthalenediol (92-44-4)

Conditions	Yield
Conversion of starting material;

C18H26O2Si (1344113-51-4) → 2,3-naphthalenediol (92-44-4)

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

β-naphthol (135-19-3) → 2,3-naphthalenediol (92-44-4)

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

naphthalene-2,3-diyl dihexanoate (438250-13-6) → 2,3-naphthalenediol (92-44-4)

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 → 2,3-naphthalenediol (92-44-4)

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

C16H10B2Cl2O2 → 4,5-dichlorocatechol (3428-24-8) + 2,3-naphthalenediol (92-44-4)

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

dimethyl sulfate (77-78-1) + 2,3-naphthalenediol (92-44-4) → 2,3-dimethoxynaphthalene (10103-06-7)

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%

2,3-naphthalenediol (92-44-4) + Triphenylphosphine oxide (791-28-6) → (2,3-naphthalenedioxy)triphenylphosphorane

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

acetyl chloride (75-36-5) + 2,3-naphthalenediol (92-44-4) → 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	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%

acetyl chloride (75-36-5) + 2,3-naphthalenediol (92-44-4) → 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	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%

indium (7440-74-6) + 2,3-naphthalenediol (92-44-4) → In{OC10H6(OH)-2,3} (121581-68-8, 121581-73-5)

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%

Trimethyl borate (121-43-7) + 2,3-naphthalenediol (92-44-4) + tetraethylene glycol monoacrylate (19812-60-3) → CH2CHC(O)(OCH2CH2)4O(BO2C10H6)

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%

tetrakis(dimethylamido)titanium(IV) + 2,3-naphthalenediol (92-44-4) → bis(dimethylamido)naphthalene-2,3-diolato-titanium(IV)

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

4-Nitrophthalonitrile (31643-49-9) + 2,3-naphthalenediol (92-44-4) → 2,3-bis-(3,4-dicyanophenoxy)naphthalene (161204-26-8)

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

4-Nitrophthalonitrile (31643-49-9) + 2,3-naphthalenediol (92-44-4) → tetranitrile + 2,3-bis-(3,4-dicyanophenoxy)naphthalene (161204-26-8)

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

methanesulfonyl chloride (124-63-0) + 2,3-naphthalenediol (92-44-4) → 2,3-bis(methylsulfonyloxy)naphthalene (22426-45-5)

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%

2,3-naphthalenediol (92-44-4) + Cinchonine → C20H12BO4(1-)*C19H22N2O*H(1+)

Conditions	Yield
With boric acid In acetone	99%

4-methyl-benzoyl chloride (874-60-2) + 2,3-naphthalenediol (92-44-4) → C26H20O4

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

boric acid (11113-50-1) + 2,3-naphthalenediol (92-44-4) + cinchonidine (1071759-34-6) → cinchonidinium (bis-2,3-naphthalenediyl)orthoborate salt

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%

PhP(Se)Se(Se)PPh(OC10H6O-2,3) + 2,3-naphthalenediol (92-44-4) → PhP(Se)(OC10H6O-2,3) (1228931-21-2)

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

allyltrimethoxysilane (2551-83-9) + tetramethyl ammoniumhydroxide (75-59-2) + 2,3-naphthalenediol (92-44-4) → tetramethylammonium bis(2,3-naphthalenediolato)allylsiliconate

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

aniline (62-53-3) + 2,3-naphthalenediol → 1-phenylazo-2,3-dihydroxynaphthalene

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%

Upstream product

• 6399-72-0 6-amino-7-hydroxy-2-naphthalenesulphonic acid 
• 52864-96-7 1,4-Dibromo-2,3-dihydroxynaphthalene 
• 672919-94-7 6,7,8-trihydroxy-[1]naphthoic acid 
• 10034-85-2 hydrogen iodide 
• 10103-06-7 2,3-dimethoxynaphthalene 
• 5656-49-5 2,2-dimethylnaphtho[2,3-d]-1,3-dioxole 
• 91-20-3 naphthalene 
• 438250-13-6 naphthalene-2,3-diyl dihexanoate 
• 33933-59-4 3-tert-butoxy-2-hydroxynaphthalene 
• 135-19-3 β-naphthol 
• 1344113-51-4 C₁₈H₂₆O₂Si 
• 22426-46-6 2,3-naphthalenediol-2,3-diacetate 

Downstream Products

• 72836-74-9 (3-hydroxy-[2]naphthyloxy)-acetic acid 
• 10103-06-7 2,3-dimethoxynaphthalene 
• 103860-60-2 2,3‐dihydroxynaphthalene‐1,4‐dicarbaldehyde 
• 10350-06-8 6,13-dihydrodibenzophenazine 
• 39215-21-9 [1,1'-binaphthalene]-2,2',3,3'-tetraol 
• 2089-80-7 2,3-Dihydroxy-1-naphthaldehyde 
• 771-97-1 2,3-Diaminonaphthalene 
• 52864-95-6 1,4-dichloro-naphthalene-2,3-diol 
• 5417-63-0 3-Amino-2-naphthol 
• 13910-42-4 N.N'-Dicyclohexyl-O-<3-hydroxy-naphthyl-(2)>-isoharnstoff 
• 3355-05-3 2,3-dihydroxy-5,6,7,8-tetrahydronaphthalene 
• 187088-54-6 2,3-bis-(3-cyanophenoxy) naphthalene 
• 195731-51-2 3-(2-hydroxyethoxy) naphthalene-2-ol 
• 20259-00-1 1-(phenylimino-methyl)-naphthalene-2,3-diol 

Relevant articles and documents

Identification of molecular crystals capable of undergoing an acyl-transfer reaction based on intermolecular interactions in the crystal lattice

Investigation of the intermolecular acyl-transfer reactivity in molecular crystals of myo-inositol orthoester derivatives and its correlation with crystal structures enabled us to identify the essential parameters to support efficient acyl-transfer reactions in crystals: 1)a the favorable geometry of the nucleophile (-OH) and the electrophile (C-O) and 2)a the molecular assembly, reinforced by C-H×××π interactions, which supports a domino-type reaction in crystals. These parameters were used to identify another reactive crystal through a data-mining study of the Cambridge Structural Database. A 2:1 co-crystal of 2,3-naphthalene diol and its di-p-methylbenzoate was selected as a potentially reactive crystal and its reactivity was tested by heating the co-crystals in the presence of solid sodium carbonate. A facile intermolecular p-toluoyl group transfer was observed as predicted. The successful identification of reactive crystals opens up a new method for the detection of molecular crystals capable of exhibiting acyl-transfer reactivity. Reactive crystal gazing? Characterization of functional groups in small organic molecules allows the prediction of their reactivity in solution, and often the structure of the resulting products with fairly good accuracy. This, however, is not true for reactions in the solid state. It was demonstrated that an understanding of the non-covalent interactions in molecular crystals can aid in identifying crystal structures that support chemical reactions (see figure). Copyright

Construction of Two-Component Chemically Reactive Supramolecular Assemblies-Acyl Migration Reactions in Cocrystals of Napthalene-2,3-Diol and Its Diesters

Reactions in solids are of contemporary interest due to applications in pharmaceutical industries to environmental sustainability. Although several reactive crystals that support chemical reactions have been identified and characterized, the same cannot be said about reactive cocrystals. Earlier we correlated the facile acyl group transfer reactions in crystals with supramolecular parameters obtained from the crystal structures. The structure-reactivity correlation revealed the requirement of proper juxtaposition of electrophile (C=O) and the nucleophile (OH) with distance (～3.2 ?) and angle (～90°) along the chain structure. The current article describes the preparation of cocrystals that are capable of supporting intermolecular acyl group transfer reactions in a group of structurally similar molecules. The cocrystals of naphthalene 2,3-diol and its corresponding diesters showed a facile solid state acyl transfer reaction, which has been well correlated with their crystal structures.

Selective Vicinal Diiodination of Polycyclic Aromatic Hydrocarbons

Vicinally diiodinated polycyclic aromatic hydrocarbons (I2-PAHs) are accessible from the corresponding diborylated B2-PAHs through boron/iodine exchange. The B2-PAHs have been prepared via twofold electrophilic borylation reactions templated by a vicinally disilylated benzene. Our protocol is applicable to fluorenes, acenes, annulated acenes, oligoaryls, and even [5]helicene. Using B2-naphthalene as the example, we have shown that the reaction scope can, in principle, be expanded to include the synthesis of vicinally dibrominated and dihydroxylated PAHs. The usefulness of the building blocks provided by our method in the field of optoelectronic materials was demonstrated by the successful conversion of I2-fluoranthene to the analogous doubly alkynylated fluoranthene emitter.

Method for synthesizing 2,3-dioxynaphthalene

The invention relates to a method for synthesizing 2,3-dioxynaphthalene. The method comprises the following steps: adding naphthalene, a catalyst and an auxiliary in a reaction solvent; heating to thetemperature of 30-70 DEG C while stirring; then dropwise adding hydrogen peroxide with the concentration being 30%; and reacting to obtain a 2,3-dioxynaphthalene solution. Compared with an existing process for preparing 2,3-dioxynaphthalene, the method for synthesizing 2,3-dioxynaphthalene is relatively low in cost and is environmentally friendly; a large number of acids and alkalis are requiredfor a traditional sulfonation and alkali fusion process and a large amount of acid-containing waste water caused by consumption of the large number of acids and alkalis are avoided, reaction conditions are gentle, energy consumption is low, and environmental protection is facilitated.