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% |
1,8-dihydroxynaphthalene
Conditions | Yield |
---|---|
With dihydrogen peroxide In tetrahydrofuran; methanol; dodecane at 20℃; | 67% |
1,8-dihydroxynaphthalene
Conditions | Yield |
---|---|
With potassium hydroxide for 0.25h; Inert atmosphere; | 60% |
1,8-dihydroxynaphthalene
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% |
Conditions | Yield |
---|---|
at 230℃; in der Kalischmelze; |
Conditions | Yield |
---|---|
With sulfuric acid at 150℃; |
Conditions | Yield |
---|---|
bei der Kalischmelze; |
8-anilino-1-naphthalenesulfonate
A
1,8-dihydroxynaphthalene
B
8-amino-1-naphthol
C
8-hydroxy-naphthalene-1-sulfonic acid
D
1-amino-naphthalene
Conditions | Yield |
---|---|
at 220 - 300℃; im Autoklaven; |
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
A
1,8-dihydroxynaphthalene
B
1-methyl pyridinium iodide
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
1,8-dihydroxynaphthalene
Conditions | Yield |
---|---|
With pyridine hydrogenfluoride In tetrahydrofuran at 25℃; |
8-Ethoxy-naphthalen-1-ol
A
1,8-dihydroxynaphthalene
B
N-ethylpyridinium iodide
Conditions | Yield |
---|---|
With pyridine; lithium iodide at 115℃; Rate constant; |
1-methoxymethoxy-8-hydroxynaphthalene
1,8-dihydroxynaphthalene
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; |
Conditions | Yield |
---|---|
With water; oxygen; titanium(IV) oxide In acetonitrile Oxidation; Irradiation; |
naphthalene
A
1,4-Dihydroxynaphthalene
B
α-naphthol
C
2,7-Dihydroxynaphthalene
D
1,8-dihydroxynaphthalene
E
1,5-dihydroxynaphthalene
F
β-naphthol
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-dihydroxynaphthalene
Conditions | Yield |
---|---|
With sulfuric acid at 160℃; |
1,8-dihydroxynaphthalene
Conditions | Yield |
---|---|
With potassium hydroxide; water |
1,8-dihydroxynaphthalene
Conditions | Yield |
---|---|
durch Kalischmelze; |
1,8-dihydroxynaphthalene
Conditions | Yield |
---|---|
With potassium hydroxide | |
With potassium hydroxide; water at 200 - 230℃; |
sulfuric acid
4,5-dihydroxy-naphthalene-1,3-disulfonic acid
1,8-dihydroxynaphthalene
Conditions | Yield |
---|---|
at 160℃; |
sulfuric acid
4,5-dihydroxy-1-naphthalene-sulfonic acid
1,8-dihydroxynaphthalene
Conditions | Yield |
---|---|
at 150℃; |
naphthalene
A
1,4-Dihydroxynaphthalene
B
1,3-dihydroxynaphthalene
C
1,8-dihydroxynaphthalene
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; |
1,8-dihydroxynaphthalene
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
1,8-dihydroxynaphthalene
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 |
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 |
1,8-dihydroxynaphthalene
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride; dihydrogen peroxide; potassium hydrogencarbonate In tetrahydrofuran; methanol; water at 0 - 40℃; for 14h; Inert atmosphere; | 19.2 mg |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: beim Verschmelzen 2: sulfuric acid / 150 °C View Scheme |
1,8-naphthylene phenylboronate
water
A
1,8-dihydroxynaphthalene
B
phenylboronic acid
Conditions | Yield |
---|---|
In dimethylsulfoxide-d6 at 20℃; |
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% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 21h; Reflux; | 100% |
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 |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; | 98% |
Conditions | Yield |
---|---|
With methanesulfonic acid; trifluoroacetic acid at 80℃; for 24h; | 97% |
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere; | 97% |
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% |
Conditions | Yield |
---|---|
In tetrahydrofuran for 1h; | 96% |
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; |
Conditions | Yield |
---|---|
With KO2 In tetrahydrofuran; toluene at -10℃; for 6h; | 95% |
Conditions | Yield |
---|---|
In hexane; dichloromethane at -78 - 20℃; | 95% |
Conditions | Yield |
---|---|
In acetonitrile Heating; | 95% |
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
1,8-dihydroxynaphthalene
Conditions | Yield |
---|---|
With methanesulfonic acid; trifluoroacetic acid at 80℃; for 24h; | 93% |
Conditions | Yield |
---|---|
In acetonitrile at 80℃; | 93% |
Conditions | Yield |
---|---|
In acetonitrile at 80℃; for 1h; | 93% |
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 |
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 70℃; for 24h; | 92% |
With potassium hydroxide | |
In potassium hydroxide for 3h; Ambient temperature; Yield given; |
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 20 - 56℃; for 20h; | 92% |
1,8-dihydroxynaphthalene
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
In acetonitrile Heating; | 92% |
thiophosgene
1,8-dihydroxynaphthalene
naphtho[1,8-de][1,3]dioxine-2-thione
Conditions | Yield |
---|---|
With pyridine; dmap In dichloromethane at -50℃; | 91% |
1,8-dihydroxynaphthalene
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
chloromethyl methyl ether
1,8-bis(methoxymethoxy)naphthalene
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
4-bromo-3-butyn-2-one
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere; Sealed tube; | 89% |
1,8-dihydroxynaphthalene
ethyl acetoacetate
10‐hydroxy‐4‐methyl‐2H‐benzo[h]chromen‐2‐one
Conditions | Yield |
---|---|
With MnSb2O6-chitosan nanocomposite In neat (no solvent) at 80℃; for 0.583333h; Pechmann Condensation; | 88% |
With sulfuric acid | |
With hydrogenchloride; ethanol |
Conditions | Yield |
---|---|
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane at 40℃; for 24h; | 88% |
1,8-dihydroxynaphthalene
5-Methoxy-1-tetralone
5-Methoxy-1,2,3,4-tetrahydrospiro<1,3>dioxine>
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% |
Molecular Structure of 1,8-Naphthalenediol (CAS NO.569-42-6):
IUPAC Name: naphthalene-1,8-diol
Empirical Formula: C10H8O2
Molecular Weight: 160.1693
H bond acceptors: 2
H bond donors: 2
Freely Rotating Bonds: 2
Polar Surface Area: 18.46 Å2
Index of Refraction: 1.725
Molar Refractivity: 47.85 cm3
Molar Volume: 120.4 cm3
Surface Tension: 64.4 dyne/cm
Density: 1.33 g/cm3
Flash Point: 193.5 °C
Enthalpy of Vaporization: 64.73 kJ/mol
Boiling Point: 375.4 °C at 760 mmHg
Vapour Pressure: 3.62E-06 mmHg at 25°C
EINECS: 209-316-5
InChI
InChI=1/C10H8O2/c11-8-5-1-3-7-4-2-6-9(12)10(7)8/h1-6,11-12H
Smiles
c12c(O)cccc2cccc1O
1,8-Naphthalenediol , with CAS number of 569-42-6, can be called 1,8-Dihydroxynaphthalene ; Naphthalene-1,8-diol .
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