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; |
Chemical Name: 1,4-Dihydroxynaphthalene
IUPAC NAME: Naphthalene-1,4-diol
CAS No.: 571-60-8
EINECS: 209-336-4
RTECS: QJ4730000
RTECS Class: Agricultural Chemical and Pesticide; Mutagen
Molecular Formula: C10H8O2
Molecular Weight: 160.17 g/mol
Melting Point: 191-192 °C (dec.)
Density: 1.33 g/cm3
Flash Point: 202.5 °C
Boiling Point: 391 °C at 760 mmHg
Following is the structure 1,4-Naphthalenediol (571-60-8):
Product Categories about 1,4-Naphthalenediol (571-60-8)are Intermediates of Dyes and Pigments;Naphthalene derivatives
The chemical synonymous of 1,4-Naphthalenediol (571-60-8) are Alpha-naphthohydroquinone;1,4-Dihydroxynaphthalene;1,4-Ndo;1,4-Naphthalenediol;1,4-Naphthohydroquinone;1,4-Napthalenediol;P-Naphthohydroquinone;Naphthalene-1,4-DIOL
1. | orl-rat LDLo:100 mg/kg | NCNSA6 National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. 5 (1953),35. |
Reported in EPA TSCA Inventory.
Poison by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes:
T: Toxic
Xn: Harmful
Risk Statements about 1,4-Naphthalenediol (571-60-8):
R24/25 Toxic in contact with skin and if swallowed.
R26 Very toxic by inhalation.
R36/37/38 Irritating to eyes, respiratory system and skin.
R41 Risk of serious damage to eyes.
R43 May cause sensitization by skin contact.
R50 Very toxic to aquatic organisms.
Safety Statements about 1,4-Naphthalenediol (571-60-8):
S24 Avoid contact with skin.
S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S28A After contact with skin, wash immediately with plenty of water.
S36/37/39 Wear suitable protective clothing, gloves and eye/face protection.
S38 In case of insufficient ventilation, wear suitable respiratory equipment.
S45 In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible).
S61 Avoid release to the environment. Refer to special instructions/safety data sheets.
Attentions:
1. Storage: Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
2. Handling: Avoid ingestion and inhalation. Avoid contact with eyes, skin, and clothing. Wash thoroughly after handling. Use with adequate ventilation. Minimize dust generation and accumulation. Keep container tightly closed. Wash clothing before reuse.
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