569-42-6

Basic information

• Product Name: 1,8-DIHYDROXYNAPHTHALENE
• Synonyms: 1,8-DIHYDROXYNAPHTHALENE;1,8-NAPHTHALENEDIOL;naphthalene-1,8-diol;1,8-dihydroxynaphtalene;1,8-Dihydroxynaphthalene 95%
• CAS NO: 569-42-6
• Molecular Formula: C₁₀H₈O₂
• Molecular Weight: 160.17
• EINECS: 209-316-5
• Mol File: 569-42-6.mol
• Article Data: 27

Chemical Properties

• Melting Point: 142-143℃
• Boiling Point: 375.4 °C at 760 mmHg
• Flash Point: 193.5 °C
• Appearance: /
• Density: 1.33
• Vapor Pressure: 3.62E-06mmHg at 25°C
• Refractive Index: 1.725
• Storage Temp.: 2-8°C
• PKA: 6.36±0.10(Predicted)
• BRN: 2044947
• CAS DataBase Reference: 1,8-DIHYDROXYNAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,8-DIHYDROXYNAPHTHALENE(569-42-6)
• EPA Substance Registry System: 1,8-DIHYDROXYNAPHTHALENE(569-42-6)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 569-42-6(Hazardous Substances Data)

Usage

Uses

1,8-Dihydroxynaphthalene (DHN) can be used as:An intermediate in the preparation of benzo analogs of spiromamakone A.A starting material to synthesize naphthopyran derivatives.An intermediate in the total synthesis of palmarumycin CP17 analogs.

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

Synthetic route

1,8-naphthosultone (83-31-8) → 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
With potassium hydroxide at 300℃; for 0.5h;	86%
With potassium hydroxide; water at 225℃; for 0.5h;	83%
With potassium hydroxide at 300℃; for 0.5h;	80%

1,1-dimethyl-1H,3H-naphtho[1,8-cd][1,2,6]oxasilaborinin-3-ol → 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
With dihydrogen peroxide In tetrahydrofuran; methanol; dodecane at 20℃;	67%

1,8-naphthalenesultone → 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
With potassium hydroxide for 0.25h; Inert atmosphere;	60%

1,8-naphthosultone → 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
Stage #1: 1,8-naphthosultone With potassium hydroxide; sodium hydroxide at 210℃; for 0.75h; Inert atmosphere; Stage #2: With sulfuric acid; water at 0℃;	53%

8-hydroxy-naphthalene-1-sulfonic acid (117-22-6) → 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
at 230℃; in der Kalischmelze;

4,5-dihydroxy-1-naphthalene-sulfonic acid (83-65-8) → 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
With sulfuric acid at 150℃;

1,8-naphthosultam (603-72-5) → 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
bei der Kalischmelze;

furan-2,3,5(4H)-trione pyridine (1:1) + 8-anilino-1-naphthalenesulfonate (82-75-7) → 1,8-dihydroxynaphthalene (569-42-6) + 8-amino-1-naphthol (2834-91-5) + 8-hydroxy-naphthalene-1-sulfonic acid (117-22-6) + 1-amino-naphthalene (134-32-7)

Conditions	Yield
at 220 - 300℃; im Autoklaven;

8-anilino-1-naphthalenesulfonate (82-75-7) → 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
With sodium hydroxide at 220 - 230℃; unter Druck;
Multi-step reaction with 2 steps 1: 92 percent / NaNO2, aq. HCl / H2O / 1 h / Heating 2: KOH / neat (no solvent) / 1.75 h / 250 - 255 °C View Scheme

8-methoxy-naphthalen-1-ol (3588-75-8) → 1,8-dihydroxynaphthalene (569-42-6) + 1-methyl pyridinium iodide (930-73-4)

Conditions	Yield
With pyridine; pyridine hydroiodide at 115℃; Rate constant; LiI, KI, var. temp.;

2,2-Di-tert-butyl-1,3-dioxa-2-sila-phenalene (81418-05-5) → 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
With pyridine hydrogenfluoride In tetrahydrofuran at 25℃;

8-Ethoxy-naphthalen-1-ol (104422-22-2) → 1,8-dihydroxynaphthalene (569-42-6) + N-ethylpyridinium iodide (872-90-2)

Conditions	Yield
With pyridine; lithium iodide at 115℃; Rate constant;

1-methoxymethoxy-8-hydroxynaphthalene (122127-76-8) → 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
With hydrogenchloride at 65℃; Rate constant;
With hydrogenchloride; ethylenediaminetetraacetic acid; buffer solution; sodium perchlorate; sodium iodide at 65℃; Rate constant; pH=3.5-9.7;

naphthalene (91-20-3) → 1,3-dihydroxynaphthalene (132-86-5) + 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
With water; oxygen; titanium(IV) oxide In acetonitrile Oxidation; Irradiation;

naphthalene (91-20-3) → 1,4-Dihydroxynaphthalene (571-60-8) + α-naphthol (90-15-3) + 2,7-Dihydroxynaphthalene (582-17-2) + 1,8-dihydroxynaphthalene (569-42-6) + 1,5-dihydroxynaphthalene (83-56-7) + β-naphthol (135-19-3) + all disubstituted naphthalenes; trisubstituted naphthalenes

Conditions	Yield
With n-butyllithium; potassium tert-butylate Product distribution; multistep reaction; isomer distribution as a function of the solvent and conditions (THF only monosubstitution), also after reaction with Me2SO4;

1.8-dioxy-naphthalene-disulfonic acid-(2.4) → 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
With sulfuric acid at 160℃;

naphthalene-sultone-(1.8) → 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
With potassium hydroxide; water

sultam of/the/ 1-oxy-naphthalene-sulfonic acid-(8) → 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
durch Kalischmelze;

sultone of/the/ 1-oxy-naphthalene-sulfonic acid-(8) → 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
With potassium hydroxide
With potassium hydroxide; water at 200 - 230℃;

sulfuric acid (7664-93-9) + 4,5-dihydroxy-naphthalene-1,3-disulfonic acid (23894-05-5) → 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
at 160℃;

sulfuric acid (7664-93-9) + 4,5-dihydroxy-1-naphthalene-sulfonic acid (83-65-8) → 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
at 150℃;

naphthalene (91-20-3) → 1,4-Dihydroxynaphthalene (571-60-8) + 1,3-dihydroxynaphthalene (132-86-5) + 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
With dihydrogen peroxide; titanium(IV) oxide In water; acetonitrile for 1h; Product distribution; Quantum yield; Further Variations:; catalyst kind, reagent concentration; dihydroxylation; Irradiation;

dimethyl-(8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-1-yl)silane → 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: [Ru(p-cypene)Cl2]2 / acetonitrile / 20 °C 2: dihydrogen peroxide / tetrahydrofuran; methanol; dodecane / 20 °C View Scheme
With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 0.25h; Inert atmosphere;	16.1 %Spectr.
Multi-step reaction with 2 steps 1: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 / neat (no solvent) / 1 h / 20 °C / Inert atmosphere 2: dihydrogen peroxide; potassium hydrogencarbonate; tetrabutyl ammonium fluoride / tetrahydrofuran; water; methanol / 14 h / 0 - 40 °C / Inert atmosphere View Scheme

dimethyl(naphthalen-1-yl)silane (38274-80-5) → 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 3,4,7,8-Tetramethyl-o-phenanthrolin; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / tetrahydrofuran / 0.08 h / 20 °C / Inert atmosphere; Glovebox 1.2: 80 °C / Inert atmosphere; Sealed tube 2.1: [Ru(p-cypene)Cl2]2 / acetonitrile / 20 °C 3.1: dihydrogen peroxide / tetrahydrofuran; methanol; dodecane / 20 °C View Scheme
Multi-step reaction with 2 steps 1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 3,4,7,8-Tetramethyl-o-phenanthrolin / tetrahydrofuran / 3 h / 80 °C / Inert atmosphere 2: dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; water / 0.25 h / 0 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 3,4,7,8-Tetramethyl-o-phenanthrolin / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 2: dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; water / 0.25 h / 0 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 3,4,7,8-Tetramethyl-o-phenanthrolin / tetrahydrofuran / 3 h / 80 °C / Inert atmosphere 2: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 / neat (no solvent) / 1 h / 20 °C / Inert atmosphere 3: dihydrogen peroxide; potassium hydrogencarbonate; tetrabutyl ammonium fluoride / tetrahydrofuran; water; methanol / 14 h / 0 - 40 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 3,4,7,8-Tetramethyl-o-phenanthrolin / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 2: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 / neat (no solvent) / 1 h / 20 °C / Inert atmosphere 3: dihydrogen peroxide; potassium hydrogencarbonate; tetrabutyl ammonium fluoride / tetrahydrofuran; water; methanol / 14 h / 0 - 40 °C / Inert atmosphere View Scheme

1-Bromonaphthalene (90-11-9) → 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere 1.2: 0.5 h / -78 - 20 °C / Inert atmosphere 2.1: 3,4,7,8-Tetramethyl-o-phenanthrolin; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / tetrahydrofuran / 0.08 h / 20 °C / Inert atmosphere; Glovebox 2.2: 80 °C / Inert atmosphere; Sealed tube 3.1: [Ru(p-cypene)Cl2]2 / acetonitrile / 20 °C 4.1: dihydrogen peroxide / tetrahydrofuran; methanol; dodecane / 20 °C View Scheme
Multi-step reaction with 3 steps 1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 20 °C / Inert atmosphere 2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 3,4,7,8-Tetramethyl-o-phenanthrolin / tetrahydrofuran / 3 h / 80 °C / Inert atmosphere 3: dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; water / 0.25 h / 0 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 20 °C / Inert atmosphere 2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 3,4,7,8-Tetramethyl-o-phenanthrolin / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 3: dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; water / 0.25 h / 0 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 20 °C / Inert atmosphere 2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 3,4,7,8-Tetramethyl-o-phenanthrolin / tetrahydrofuran / 3 h / 80 °C / Inert atmosphere 3: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 / neat (no solvent) / 1 h / 20 °C / Inert atmosphere 4: dihydrogen peroxide; potassium hydrogencarbonate; tetrabutyl ammonium fluoride / tetrahydrofuran; water; methanol / 14 h / 0 - 40 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 20 °C / Inert atmosphere 2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 3,4,7,8-Tetramethyl-o-phenanthrolin / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 3: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 / neat (no solvent) / 1 h / 20 °C / Inert atmosphere 4: dihydrogen peroxide; potassium hydrogencarbonate; tetrabutyl ammonium fluoride / tetrahydrofuran; water; methanol / 14 h / 0 - 40 °C / Inert atmosphere View Scheme

methoxydimethyl(8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-1-yl)silane → 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
With tetrabutyl ammonium fluoride; dihydrogen peroxide; potassium hydrogencarbonate In tetrahydrofuran; methanol; water at 0 - 40℃; for 14h; Inert atmosphere;	19.2 mg

1-naphthol-4,8-disulfonic acid (117-56-6) → 1,8-dihydroxynaphthalene (569-42-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: beim Verschmelzen 2: sulfuric acid / 150 °C View Scheme

1,8-naphthylene phenylboronate (60548-84-7) + water (7732-18-5) → 1,8-dihydroxynaphthalene (569-42-6) + phenylboronic acid (98-80-6)

Conditions	Yield
In dimethylsulfoxide-d6 at 20℃;

1,8-dihydroxynaphthalene (569-42-6) + methyl iodide (74-88-4) → 1,8-dimethoxy-naphthalene (10075-66-8)

Conditions	Yield
With potassium carbonate In acetone for 24h; Inert atmosphere; Reflux;	100%
With Aliquat (at)366; sodium hydroxide at 60 - 70℃; for 2h;	70%
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane at 40℃; for 45h;	67%

1,8-dihydroxynaphthalene (569-42-6) + ethyl bromoacetate (105-36-2) → diethyl 2,2'-(naphthalene-1,8-diylbis(oxy))diacetate

Conditions	Yield
With potassium carbonate In acetone for 21h; Reflux;	100%

1,8-dihydroxynaphthalene (569-42-6) + dimethyl sulfate (77-78-1) → 8-methoxy-naphthalen-1-ol (3588-75-8)

Conditions	Yield
Stage #1: 1,8-dihydroxynaphthalene With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere; Stage #2: dimethyl sulfate In tetrahydrofuran; mineral oil at 0 - 25℃; Inert atmosphere;	99%
Stage #1: 1,8-dihydroxynaphthalene With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere; Stage #2: dimethyl sulfate In tetrahydrofuran; mineral oil at 0 - 25℃; for 14h;	99%
With sodium hydroxide
With sodium hydroxide In diethyl ether

Trimethyl borate (121-43-7) + 1,8-dihydroxynaphthalene (569-42-6) → C11H9BO3

Conditions	Yield
In dichloromethane at 20℃;	98%

1,8-dihydroxynaphthalene (569-42-6) + 2-(4-amino-2-hydroxybenzoyl)benzoic acid → C24H15NO4

Conditions	Yield
With methanesulfonic acid; trifluoroacetic acid at 80℃; for 24h;	97%

1-benzoyl-2-bromoacetylene (3876-61-7) + 1,8-dihydroxynaphthalene (569-42-6) → 2-(naphtho[1,8-de][1,3]dioxin-2-ylidene)-1-phenylethan-1-one

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;	97%

1,8-dihydroxynaphthalene (569-42-6) + methyl iodide (74-88-4) → 8-methoxy-naphthalen-1-ol (3588-75-8)

Conditions	Yield
With potassium carbonate In acetone at 23℃; for 24h;	96%
Stage #1: 1,8-dihydroxynaphthalene; methyl iodide With potassium carbonate In acetone at 18℃; for 10h; Stage #2: With hydrogenchloride In water; acetone	95%
With caesium carbonate In acetone for 4h; Inert atmosphere; Reflux;	84.4%

tris(dimethylamino)borane (4375-83-1) + 1,8-dihydroxynaphthalene (569-42-6) → C20H12BO4(1-)*H(1+)*C2H7N

Conditions	Yield
In tetrahydrofuran for 1h;	96%

1,8-dihydroxynaphthalene (569-42-6) → 8-hydroxy-1,2,3,4-tetrahydro-1-naphthalenone (7695-47-8)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol at 60℃; under 3040.2 Torr; for 48h; Autoclave;	95%
With palladium on activated charcoal; hydrogen In ethanol at 60℃; for 24h;	74%
With aluminum (III) chloride In cyclohexane at 110℃; for 2h; Sealed tube;	70%
With aluminum (III) chloride In cyclohexane at 110℃; for 2h; Sealed tube;	30%
With ethanol; nickel Hydrogenation;

1,8-dihydroxynaphthalene (569-42-6) → 3,5-dihydroxy-2,3-dihydro-1,4-naphthoquinone (4923-58-4)

Conditions	Yield
With KO2 In tetrahydrofuran; toluene at -10℃; for 6h;	95%

1,8-dihydroxynaphthalene (569-42-6) + boron trichloride (10294-34-5) → C10H6BClO2

Conditions	Yield
In hexane; dichloromethane at -78 - 20℃;	95%

1,8-dihydroxynaphthalene (569-42-6) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → C16H8BF3O2

Conditions	Yield
In acetonitrile Heating;	95%

1,8-dihydroxynaphthalene (569-42-6) + benzene (71-43-2) → 8-hydroxy-4-phenyl-1-tetralone

Conditions	Yield
With aluminum (III) chloride at 20℃; for 48h; Reagent/catalyst;	93%

2-(8-hydroxy-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-9-carbonyl)benzoic acid (107070-67-7) + 1,8-dihydroxynaphthalene (569-42-6) → C30H23NO4

Conditions	Yield
With methanesulfonic acid; trifluoroacetic acid at 80℃; for 24h;	93%

butylboronic acid (4426-47-5) + 1,8-dihydroxynaphthalene (569-42-6) → C14H15BO2

Conditions	Yield
In acetonitrile at 80℃;	93%

1,8-dihydroxynaphthalene (569-42-6) + boric acid (11113-50-1) → C10H7BO3

Conditions	Yield
In acetonitrile at 80℃; for 1h;	93%

1,8-dihydroxynaphthalene (569-42-6) → 5-hydroxynaphtho-1,4-quinone (481-39-0)

Conditions	Yield
With K10 montmorillonite; iodic acid for 0.366667h; Heating;	92%
With 1,1,1,3',3',3'-hexafluoro-propanol; urea hydrogen peroxide adduct at 45℃; Sealed tube; Green chemistry;	83%
With potassium nitrososulfonate; acetone

1,8-dihydroxynaphthalene (569-42-6) + dimethyl sulfate (77-78-1) → 1,8-dimethoxy-naphthalene (10075-66-8)

Conditions	Yield
With potassium carbonate In acetone at 70℃; for 24h;	92%
With potassium hydroxide
In potassium hydroxide for 3h; Ambient temperature; Yield given;

2-iodo-propane (75-30-9) + 1,8-dihydroxynaphthalene (569-42-6) → 8-isopropoxynaphthalen-1-ol (1257243-81-4)

Conditions	Yield
With potassium carbonate In acetone at 20 - 56℃; for 20h;	92%

1,8-dihydroxynaphthalene (569-42-6) + 1-bromo-4,4-dimethyl-1-pentyn-3-one → 3,3-dimethyl-1-(naphtho[1,8-de][1,3]dioxin-2-ylidene)butan-2-one

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;	92%

1,8-dihydroxynaphthalene (569-42-6) + 2,4,6-trifluorophenylboronic acid (182482-25-3) → C16H8BF3O2

Conditions	Yield
In acetonitrile Heating;	92%

thiophosgene (463-71-8) + 1,8-dihydroxynaphthalene (569-42-6) → naphtho[1,8-de][1,3]dioxine-2-thione (524047-44-7)

Conditions	Yield
With pyridine; dmap In dichloromethane at -50℃;	91%

1,8-dihydroxynaphthalene (569-42-6) → 4-nitro-1,8-naphthalene diol

Conditions	Yield
With copper nitrate hemi(pentahydrate); acetic anhydride; acetic acid at 25℃; for 5h;	91%
With aluminum(III) nitrate nonahydrate; acetic anhydride; acetic acid at 20℃; for 6h;	90%

1,8-dihydroxynaphthalene (569-42-6) + chloromethyl methyl ether (107-30-2) → 1,8-bis(methoxymethoxy)naphthalene (172915-62-7)

Conditions	Yield
Stage #1: 1,8-dihydroxynaphthalene With sodium hydride In N,N-dimethyl-formamide at 0℃; Stage #2: chloromethyl methyl ether In diethyl ether; N,N-dimethyl-formamide for 6h;	90%
With sodium hydride In diethyl ether; N,N-dimethyl-formamide at 25℃;	88%
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h;	85%

1,8-dihydroxynaphthalene (569-42-6) + 4-bromo-3-butyn-2-one (87293-26-3) → 1-(naphtho[1,8-de][1,3]dioxin-2-ylidene)propan-2-one

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;	89%

1,8-dihydroxynaphthalene (569-42-6) + chlorophosphoric acid diphenyl ester (2524-64-3) → 2-Phenoxy-1,3-dioxa-2-phospha-phenalene 2-oxide

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere; Sealed tube;	89%

1,8-dihydroxynaphthalene (569-42-6) + ethyl acetoacetate (141-97-9) → 10‐hydroxy‐4‐methyl‐2H‐benzo[h]chromen‐2‐one (33396-80-4)

Conditions	Yield
With MnSb2O6-chitosan nanocomposite In neat (no solvent) at 80℃; for 0.583333h; Pechmann Condensation;	88%
With sulfuric acid
With hydrogenchloride; ethanol

1,8-dihydroxynaphthalene (569-42-6) + ethyl iodide (75-03-6) → 8-Ethoxy-naphthalen-1-ol (104422-22-2)

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane at 40℃; for 24h;	88%

1,8-dihydroxynaphthalene (569-42-6) + 5-Methoxy-1-tetralone (33892-75-0) → 5-Methoxy-1,2,3,4-tetrahydrospiro<1,3>dioxine> (207504-79-8)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 48h; Heating;	86%
With sulfuric acid In toluene for 72h; Heating;	69%
With toluene-4-sulfonic acid In toluene for 72h; Reflux;	57%
With 4 A molecular sieve; p-toluenesulfonic acid monohydrate In toluene for 72h; Heating;	53%

Upstream product

• 82-75-7 8-anilino-1-naphthalenesulfonate 
• 91-20-3 naphthalene 
• 7664-93-9 sulfuric acid 
• 23894-05-5 4,5-dihydroxy-naphthalene-1,3-disulfonic acid 
• 83-65-8 4,5-dihydroxy-1-naphthalene-sulfonic acid 
• 60548-84-7 1,8-naphthylene phenylboronate 
• 7732-18-5 water 
• 83-31-8 1,8-naphthosultone 
• 122127-76-8 1-methoxymethoxy-8-hydroxynaphthalene 
• 104422-22-2 8-Ethoxy-naphthalen-1-ol 
• 81418-05-5 2,2-Di-tert-butyl-1,3-dioxa-2-sila-phenalene 
• 3588-75-8 8-methoxy-naphthalen-1-ol 
• 603-72-5 1,8-naphthosultam 
• 117-22-6 8-hydroxy-naphthalene-1-sulfonic acid 

Downstream Products

• 479-27-6 naphthalene-1,8-diamine 
• 127837-52-9 Ti(NO(C₆H₅)(C₅H₃O₂))2(C₁₀H₆O₂) 
• 184221-86-1 4-bromo-8-methoxynaphthalen-1-ol 
• 1242319-39-6 C₄₂H₄₀O₈ 
• 1311430-82-6 methyl 3,5-dicyano-4-(8-hydroxynaphthalen-1-yloxy)benzoate 
• 1311430-85-9 methyl 3,5-bis((tert-butoxycarbonylamino)methyl)-4-(8-hydroxynaphthalen-1-yloxy)benzoate 
• 1311430-92-8 tert-butyl (2-(8-hydroxynaphthalen-1-yloxy)-1,3-phenylene)bis(methylene)dicarbamate 
• 1311430-94-0 C₁₈H₁₈N₂O₂ 
• 1311430-89-3 2-(8-hydroxynaphthalen-1-yloxy)isophthalonitrile 
• 60548-84-7 1,8-naphthylene phenylboronate 
• 120-80-9 benzene-1,2-diol 

Relevant articles and documents

First report of a permanent open form of a naphthopyran

The synthesis of a permanent open form of a naphthopyran is described for the first time. The open form of the 10-hydroxy-2H-naphtho[1,2-b]pyran, obtained by reaction of 1,8-dihydroxy-naphthalene with 1,1-diphenylprop-2-yn-1-ol under acid catalysis, is stable due to the establishment of an intramolecular hydrogen bond.

Hydrosilyl Group-directed Iridium-catalyzed peri-Selective CH Borylation of Ring-fused (Hetero)Arenes

The iridium-catalyzed direct CH borylation of ring-fused (hetero)arenes afforded borylated products in a peri-selective manner, directed by a proximal hydrosilyl group. Further selective transformations of the boryl and silyl groups enabled the synthesis of various multisubstituted (hetero)arenes, such as 1,8-disubstituted naphthalenes and 3,4-diarylindole.

Synthesis of naphthalenophane-type macrocyclic compounds using Mn(III)-based dihydrofuran-clipping reaction

The Mn(III)-based oxidation of 2,7-, 1,8-, and 1,5-disubstituted naphthalenes bearing both the 1,4-dioxa-7,7-diphenylhep-6-enyl and 1,4-dioxa-5,7-dioxooctyl groups gave new [12]naphthalenophanes along with the corresponding diploids via assembly of the dihydrofuran ring. A similar reaction of the 2,6-disubstituted naphthalene having the same substituents did not produce the naphthalenophane, but the diploid, [12,12](2,6)naphthalenophane, was obtained in a small amount. The 2,6-disubstituted naphthalene tethered to the 1,4,7-trioxa-10,10-diphenyldec-9-enyl and 1,4,7-trioxa-8,10-dioxoundecyl groups also underwent the dihydrofuran-clipping reaction to afford a trace amount of the desired [18](2,6)naphthalenophane. The reaction details and the structure determination of the products are described.