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1,4-dihydroxynaphthaleneAppearance:detailed see specifications Storage:Keep away of light, cool place Package:25kg/drum;200kg/drum Application:An important raw material and intermediate used in Organic Synthesis, Pharmaceuticals Transportation:Sea/ai
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1,4-DIHYDROXYNAPHTHALENEAppearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:intermediate Transportation:by air, by sea, by express
Conditions | Yield |
---|---|
With acetic acid; zinc Ambient temperature; sonication, less than 5 min; | 100% |
With hydrogen; palladium 10% on activated carbon under 2585.81 Torr; for 6h; | 100% |
With sodium dithionite In diethyl ether; water at 20℃; for 1h; | 100% |
3-mercaptopropionic acid ethyl ester
[1,4]naphthoquinone
A
1,4-Dihydroxynaphthalene
B
2-[2-(ethoxycarbonyl)ethyl]thio-1,4-naphthoquinone
Conditions | Yield |
---|---|
In ethanol at 20℃; Substitution; | A n/a B 93% |
1,4-diacetoxynaphthalene
A
1,4-Dihydroxynaphthalene
B
1-acetoxy-4-hydroxynaphthalene
Conditions | Yield |
---|---|
With lipase of Pseudomonas sp; water In various solvent(s) at 25℃; for 2.5h; Hydrolysis; deacetylation; | A n/a B 89% |
Conditions | Yield |
---|---|
With [O=P(2-py)3W(CO)(NO)2](BF4)2 In water at 20℃; for 1.5h; Diels-Alder reaction; | 85% |
butyraldehyde
[1,4]naphthoquinone
A
1,4-Dihydroxynaphthalene
B
1-(1,4-dihydroxynaphthalen-2-yl)butan-1-one
Conditions | Yield |
---|---|
In acetone Irradiation; Inert atmosphere; Flow reactor; Green chemistry; | A 7 %Spectr. B 83% |
With 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide for 16h; Friedel Crafts acylation; Irradiation; Inert atmosphere; chemoselective reaction; | A n/a B 40% |
In acetone; iso-butanol for 14.5h; Friedel-Crafts Acylation; Irradiation; Green chemistry; |
Hepta<2.2.2>starphen-5,6,11,12,17,18-hexaol
A
1,4-Dihydroxynaphthalene
B
Hepta<2.2.2>starphen-5,18:6,11:12,17-trichinon
C
5,12,17,18-Tetrahydroxyhepta<2.2.2>starphen-6,11-chinon
Conditions | Yield |
---|---|
With [1,4]naphthoquinone In acetic acid at 100℃; for 0.0833333h; Yield given; | A n/a B n/a C 80% |
With [1,4]naphthoquinone In acetic acid at 100℃; for 0.0833333h; Yields of byproduct given; | A n/a B n/a C 80% |
Conditions | Yield |
---|---|
In ethanol at 20℃; for 4h; | A 65% B n/a |
Conditions | Yield |
---|---|
With iodosylbenzene; racemic (salen)Mn(III) In acetonitrile at 0℃; for 3h; | 63% |
3-mercaptopropionic acid
[1,4]naphthoquinone
A
1,4-Dihydroxynaphthalene
B
3-[(1,4-dioxo-1,4-dihydronaphthalene-2-yl)thio]propionic acid
Conditions | Yield |
---|---|
Stage #1: 3-mercaptopropionic acid; [1,4]naphthoquinone In ethanol at 20℃; for 24h; Stage #2: With lead dioxide In chloroform at 20℃; for 4h; | A n/a B 52% |
[(R)-1-(3,4-Dimethoxy-phenyl)-ethyl]-(4-methoxy-naphthalen-1-yl)-amine
A
1,4-Dihydroxynaphthalene
B
1-(R)-(3,4-dimethoxyphenyl)ethylamine
Conditions | Yield |
---|---|
Stage #1: [(R)-1-(3,4-Dimethoxy-phenyl)-ethyl]-(4-methoxy-naphthalen-1-yl)-amine With ammonium cerium(IV) nitrate In water; acetonitrile Oxidation; C-N bond cleavage; Stage #2: With sodium tetrahydroborate In water; acetonitrile Reduction; | A n/a B 47% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; pH=12; | A n/a B 41% |
Conditions | Yield |
---|---|
With oxygen; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 83℃; under 760.051 Torr; Diels-Alder Cycloaddition; Reflux; | 41% |
(3-methyl-2-butenyl)trifluorosilane
[1,4]naphthoquinone
A
1,4-Dihydroxynaphthalene
B
deoxylapachol
C
2,2-di-(3-methyl-but-2-enyl)-2,3-dihydro-1,4-naphthoquinone
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at -20℃; for 1h; | A 38% B 28% C 32% |
[1,4]naphthoquinone
A
1,4-Dihydroxynaphthalene
B
deoxylapachol
C
2,2-di-(3-methyl-but-2-enyl)-2,3-dihydro-1,4-naphthoquinone
Conditions | Yield |
---|---|
With (3-methyl-2-butenyl)trifluorosilane; tetrabutyl ammonium fluoride In tetrahydrofuran at -20℃; for 1h; | A 38% B 28% C 32% |
Dodecanal
[1,4]naphthoquinone
A
1,4-Dihydroxynaphthalene
B
1-(1,4-dihydroxynaphthalen-2-yl)-dodecan-1-one
Conditions | Yield |
---|---|
In acetone Irradiation; Inert atmosphere; Flow reactor; Green chemistry; | A 7 %Spectr. B 32% |
With 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide for 16h; Friedel Crafts acylation; Irradiation; Inert atmosphere; chemoselective reaction; |
ethylaluminum dichloride
[1,4]naphthoquinone
A
1,4-Dihydroxynaphthalene
B
4-ethoxy-1-naphthol
Conditions | Yield |
---|---|
In toluene at -78℃; for 2h; | A 26% B 44 % Spectr. |
Conditions | Yield |
---|---|
With ethylaluminum dichloride In toluene at -78℃; for 2h; | A 26% B 44 % Spectr. |
[1,4]naphthoquinone
A
1,4-Dihydroxynaphthalene
B
2-chloro-1,4-dihydroxynaphthalene
Conditions | Yield |
---|---|
With (Z)-3-methyl-2-butenyltrichlorosilane In formamide for 24h; Ambient temperature; | A 23% B 18% |
2-vinylthiophene
[1,4]naphthoquinone
A
1,4-Dihydroxynaphthalene
B
4,5,6,11-tetrahydro-6,11-dioxoanthra<2,1-b>thiophene
Conditions | Yield |
---|---|
In toluene for 48h; Heating; | A n/a B 22% |
Conditions | Yield |
---|---|
With peroxygenase; dihydrogen peroxide In acetonitrile at 20℃; for 0.416667h; pH=3; pH-value; Enzymatic reaction; | A 15.4% B 6.7% |
2-vinyl-4-methylthiophene
[1,4]naphthoquinone
A
1,4-Dihydroxynaphthalene
B
6,11-dihydro-1-methyl-6,11-dioxoanthra<2,1-b>thiophene
C
4,5,6,11-tetrahydro-1-methyl-6,11-dioxoanthra<2,1-b>thiophene
Conditions | Yield |
---|---|
In toluene for 48h; Heating; | A n/a B 10% C 5% |
Conditions | Yield |
---|---|
((2-O-C6H4CN)2CH2C(CH3)2)Cu for 12h; | A 4.8% B 6.9% |
1,4-dioxane
1,1-Bisethylene
[1,4]naphthoquinone
A
1,4-Dihydroxynaphthalene
Conditions | Yield |
---|---|
at 70℃; unter Lichtausschluss; |
Conditions | Yield |
---|---|
With sodium hydroxide; dipotassium peroxodisulfate | |
With sodium hydroxide; ammonium peroxydisulfate | |
With CYP175A1; dihydrogen peroxide In aq. phosphate buffer at 50℃; for 1h; pH=7.5; Kinetics; Enzymatic reaction; |
Conditions | Yield |
---|---|
With sodium metabisulfite; sodium hydroxide; ozone weiteres Reagens: Sauerstoff; |
Conditions | Yield |
---|---|
With sulfuric acid |
4-amino-1-naphthalenesufonic acid
A
1,4-Dihydroxynaphthalene
B
α-naphthol
C
1-hydroxy-4-naphthalenesulfonate
Conditions | Yield |
---|---|
at 220 - 300℃; im Autoklaven; |
Conditions | Yield |
---|---|
With sodium hydroxide at 220 - 300℃; unter Druck; |
Conditions | Yield |
---|---|
With sodium hydroxide; ethanol Kochen des Reaktionsgemisches mit konz. wss. HCl und SnCl2; | |
Multi-step reaction with 5 steps 1: sodium tetrahydroborate / methanol 2: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 3: sodium hydroxide / ethanol / 3 h / 0 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 0.33 h / 120 °C / Microwave irradiation; Inert atmosphere 5: dihydrogen peroxide View Scheme |
Conditions | Yield |
---|---|
With ethanol; sulfuric acid |
Conditions | Yield |
---|---|
With 2,2'-bipyridylchromium peroxide In benzene for 0.5h; Heating; | 100% |
With dihydrogen peroxide; bis-(tributyltin oxide) dioxochromium(VI) In benzene at 50℃; for 1.5h; | 100% |
With 2,2'-bipyridylchromium peroxide In benzene for 0.5h; Product distribution; Heating; effect of various chromium(VI) based oxidants; | 100% |
[2-(2-thyenyl)ethyl]amine
1,4-Dihydroxynaphthalene
Conditions | Yield |
---|---|
With cerium(III) chloride heptahydrate; triethylamine In ethanol at 20℃; Further stages; | 100% |
Conditions | Yield |
---|---|
In dichloromethane at 35℃; Flow reactor; | 99% |
With pyridine at 0 - 20℃; for 16h; Reflux; | 86% |
Conditions | Yield |
---|---|
With dmap In dichloromethane at 35℃; Flow reactor; | 99% |
Conditions | Yield |
---|---|
With potassium hydroxide In tetrahydrofuran; water Flow reactor; | 97% |
With barium dihydroxide; hydrogen; palladium on activated charcoal In N,N-dimethyl-formamide | 92% |
With potassium carbonate In acetone for 1h; Reflux; | 89% |
Conditions | Yield |
---|---|
With hydrogenchloride for 0.25h; | 97% |
Conditions | Yield |
---|---|
With palladium(II) acetylacetonate; dimethyl sulfoxide; silver carbonate; Trimethylacetic acid at 140℃; for 24h; Catalytic behavior; Reagent/catalyst; Sealed tube; | 97% |
1,4-Dihydroxynaphthalene
diethylene glycol
4-(1,4,7-Trioxaheptyl)-1-naphthol
Conditions | Yield |
---|---|
With hydrogenchloride | 96% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 1h; Heating; | 96% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 1h; Heating; | 96% |
Conditions | Yield |
---|---|
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3h; Inert atmosphere; | 96% |
methanol
1,4-Dihydroxynaphthalene
A
4-methoxynaphth-1-ol
B
1,4-dimethoxynaphthalene
Conditions | Yield |
---|---|
With hydrogenchloride for 0.25h; Mechanism; | A 95% B 2% |
With hydrogenchloride for 0.25h; | A 95% B 2% |
With boron trifluoride |
Conditions | Yield |
---|---|
With hydrogenchloride for 0.25h; | 95% |
With hydrogenchloride |
Conditions | Yield |
---|---|
With hydrogenchloride for 0.25h; | 95% |
With boron trifluoride at 80℃; | |
With hydrogenchloride |
1,4-Dihydroxynaphthalene
1,3-diphenyl-benzo[c]thiophene-5,6-dicarbaldehyde
1,3-Diphenylnaphthaceno<2,3-c>thiophene-6,11-quinone
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In chloroform for 4h; Heating; | 95% |
1,4-Dihydroxynaphthalene
2-chloro-ethanol
4-(2-chloroethoxy)-1-naphthol
Conditions | Yield |
---|---|
With hydrogenchloride for 0.25h; | 95% |
With hydrogenchloride | 94% |
With hydrogenchloride at 20℃; for 7h; Inert atmosphere; | 91% |
1,4-Dihydroxynaphthalene
N-Boc-1,3-diaminopropane
tert-butyl 3-(4-hydroxynaphth-1-ylamino)propylcarbamate
Conditions | Yield |
---|---|
In toluene at 120℃; for 1h; | 95% |
Conditions | Yield |
---|---|
With pyridine at 20℃; for 1h; | 94% |
With pyridine at 20℃; for 5h; | 83% |
In pyridine at 20℃; for 1h; | 54% |
With zinc(II) chloride | |
With sodium acetate |
Conditions | Yield |
---|---|
With hydrogenchloride for 0.25h; | 94% |
1,4-Dihydroxynaphthalene
5-chloro-2-methyl-4-nitroaniline
2-chloro-5-methyl-1,4-phenylenediamine
Conditions | Yield |
---|---|
With sodium hydroxide In water; toluene | 94% |
Conditions | Yield |
---|---|
With hydrogenchloride for 0.25h; | 93% |
With hydrogenchloride |
1,4-Dihydroxynaphthalene
iso-butanol
4-sec-Butoxy-1-naphthol
Conditions | Yield |
---|---|
With hydrogenchloride for 0.25h; | 93% |
1,4-Dihydroxynaphthalene
2-methoxy-ethanol
4-(2-Methoxyethoxy)-1-naphthol
Conditions | Yield |
---|---|
With hydrogenchloride for 0.25h; | 92% |
1,4-Dihydroxynaphthalene
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
4-(1,4,7,10-Tetraoxadecyl)-1-naphthol
Conditions | Yield |
---|---|
With hydrogenchloride | 92% |
Conditions | Yield |
---|---|
With cerium(III) chloride heptahydrate; triethylamine In ethanol at 20℃; for 4h; | 92% |
With cerium(III) chloride heptahydrate; triethylamine In ethanol at 20℃; for 6h; | 92% |
Conditions | Yield |
---|---|
With potassium hydroxide In tetrahydrofuran; water for 4h; Reflux; | 90% |
1,4-Dihydroxynaphthalene
trifluoromethylsulfonic anhydride
naphthalene-1,4-diyl bis(trifluoromethanesulfonate)
Conditions | Yield |
---|---|
In dichloromethane Flow reactor; | 89% |
With pyridine at 20℃; for 2h; Cooling with ice; | 72.6% |
With pyridine 1.) 0 deg C, 5 min, 2.) 0 deg C to r.t., 24 h; Yield given; |
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