Conditions | Yield |
---|---|
With air; C32H36Br2N4 In methanol; dichloromethane at 20℃; for 1h; Irradiation; | 100% |
With C39H50N7O2S(1+)*F6P(1-); N,N,N-trimethyl-N-propylammonium bis(trifluoromethanesulfonyl)imide at 25℃; for 3h; Kinetics; UV-irradiation; | 100% |
With C171H45BF2N4; oxygen In methanol; dichloromethane at 20℃; Kinetics; Quantum yield; Reagent/catalyst; | 99.9% |
Conditions | Yield |
---|---|
With water; trifluoroacetic acid at 72℃; for 0.75h; | 95% |
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 |
[1,4]naphthoquinone
A
5-hydroxynaphtho-1,4-quinone
B
5,8-Dihydroxy-1,4-naphthoquinone
Conditions | Yield |
---|---|
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; trifluoroacetic acid; trifluoroacetic anhydride; bis-[(trifluoroacetoxy)iodo]benzene at 80℃; for 12h; Reagent/catalyst; Sealed tube; chemoselective reaction; | A 92% B 3% |
1,5-dihydroxynaphthalene
A
5-hydroxynaphtho-1,4-quinone
B
5-hydroxy-1,2-naphthoquinone
Conditions | Yield |
---|---|
With oxygen; salcomine In acetonitrile Product distribution; without catalyst-using methylene blue/irradiation instead, with various quenchers; | A 90% B 7% |
With salcomine; oxygen In acetonitrile Product distribution; Ambient temperature; other solvents, other temp., other reactive oxygen-compounds; | A 90% B 7% |
With salcomine; oxygen In acetonitrile for 0.5h; Ambient temperature; | A 71% B 14% |
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 20℃; | 81% |
2-Methyl-1,5-naphthalindiol-5-acetat
5-hydroxynaphtho-1,4-quinone
Conditions | Yield |
---|---|
With oxygen; methylene blue In acetonitrile at 20℃; for 4h; Irradiation; | 78% |
5-hydroxynaphthalen-1-yl acetate
5-hydroxynaphtho-1,4-quinone
Conditions | Yield |
---|---|
With Rose Bengal on Merrifield resin; oxygen In acetone at 20℃; for 5h; UV-irradiation; | 68% |
With oxygen; methylene blue In acetonitrile at 20℃; for 4h; Irradiation; | 61% |
With rose bengal In tert-Amyl alcohol Irradiation; Heating; | 30% |
Conditions | Yield |
---|---|
With dihydrogen peroxide | 62% |
Conditions | Yield |
---|---|
With triethylamine In chloroform at -20℃; for 0.5h; Diels-Alder reaction; | 60% |
2,3,4,5,6-pentafluoroaniline
1,5-dihydroxynaphthalene
A
5-hydroxynaphtho-1,4-quinone
Conditions | Yield |
---|---|
With iodic acid In ethanol; water at 20℃; for 2h; | A 25% B 45% |
2,5-dihydroxy-2,3-dihydrobenzofuran
A
5-hydroxynaphtho-1,4-quinone
B
juglone
Conditions | Yield |
---|---|
With acid | A 15% B 44% |
2,3-epoxy-5-hydroxy-2,3-dihydro-1,4-naphthoquinone
A
5-hydroxynaphtho-1,4-quinone
B
3,5-dihydroxy-2,3-dihydro-1,4-naphthoquinone
C
2-Hydroxyjuglon
Conditions | Yield |
---|---|
With sodium acetate; acetic acid; sodium iodide; zinc for 1.5h; Ambient temperature; | A 33% B n/a C n/a |
C31H26O9
A
5-hydroxynaphtho-1,4-quinone
B
1,8-dihydroxy-11-methoxy-7,8,9,10-tetrahydronaphthacece-5,12-dione
Conditions | Yield |
---|---|
With base In methanol | A n/a B 7% |
Conditions | Yield |
---|---|
With iron(III) chloride | |
With bromine | |
With air | |
Multi-step reaction with 3 steps 1.1: sulphuric acid / 18 h 2.1: 420 mg / potassium carbonate / acetone / 3 h / Heating 3.1: hydrochloric acid 3.2: oxygen View Scheme |
Conditions | Yield |
---|---|
With iron(III) chloride; acetic acid |
Conditions | Yield |
---|---|
With diacetylnitric acid |
5-methoxynaphthalen-1-ol
A
5-hydroxynaphtho-1,4-quinone
B
5-methoxynaphthoquinone
C
8-Hydroxy-4-methoxy-1,2-naphthochinon
Conditions | Yield |
---|---|
With oxygen; methylene blue In methanol at 22℃; for 12h; Irradiation; |
1,8-dihydroxynaphthalene
A
5-hydroxynaphtho-1,4-quinone
B
8,8'-bijuglone
Conditions | Yield |
---|---|
Product distribution; oxidation; |
5-amino-8-hydroxy-[1,4]naphthoquinone
5-hydroxynaphtho-1,4-quinone
Conditions | Yield |
---|---|
With sodium hydroxide; hypophosphorous acid; sodium nitrite 1.) water, 2.) 40 deg C, 2 h; room temp., 10 h; Yield given. Multistep reaction; |
5-Methoxy-1-methylbenzindazol-4,9-chinon
5-hydroxynaphtho-1,4-quinone
Conditions | Yield |
---|---|
With aluminium trichloride In chloroform Heating; |
(-)-(4S)-4,8-dihydroxy-α-tetralone
5-hydroxynaphtho-1,4-quinone
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 8h; Heating; | 10 mg |
5-hydroxynaphtho-1,4-quinone
Conditions | Yield |
---|---|
With ethanol; iron(III) chloride nach vorhergegangener Bildung von α-Hydrojuglon; |
5-hydroxynaphtho-1,4-quinone
Conditions | Yield |
---|---|
With water; iron(III) chloride |
5-hydroxynaphtho-1,4-quinone
Conditions | Yield |
---|---|
With 4-sulfobenzenediazonium Reduzieren des Gebildeten Azofarbstoffs mit Zn und HCl und Oxidieren des Reduktionsprodukts mit FeCl3; |
5-hydroxynaphtho-1,4-quinone
Conditions | Yield |
---|---|
With hydrogenchloride; iron(III) chloride |
Conditions | Yield |
---|---|
With silver(l) oxide In dichloromethane for 25h; Ambient temperature; | 100% |
With silver(l) oxide In chloroform at 20℃; | 100% |
With silver(l) oxide In chloroform Heating; | 98% |
2-iodo-propane
5-hydroxynaphtho-1,4-quinone
5-isopropoxy-1,4-naphthoquinone
Conditions | Yield |
---|---|
With silver(l) oxide In dichloromethane at 20℃; for 20h; Green chemistry; regioselective reaction; | 100% |
With silver(l) oxide In chloroform for 0.333333h; Ambient temperature; | 77% |
5-hydroxynaphtho-1,4-quinone
cyclopenta-1,3-diene
(1R*,4S*,4aR*,9aS*)-1,4,4a,9a-tetrahydro-5-hydroxy-1,4-methano-9,10-anthracenedione
Conditions | Yield |
---|---|
In chloroform for 0.5h; Ambient temperature; | 100% |
In propan-1-ol at 25℃; Thermodynamic data; Rate constant; other solvents and their mixture with water; isobaric activation parameters; | |
In dichloromethane at 20℃; Reflux; |
Conditions | Yield |
---|---|
Stage #1: 5-hydroxynaphtho-1,4-quinone In ethanol for 0.25h; Stage #2: 2-Fluoroaniline In ethanol for 4h; Reflux; | 100% |
Conditions | Yield |
---|---|
With sodium dithionite In water; ethyl acetate at 30℃; for 0.5h; Inert atmosphere; | 99% |
With sodium dithionite In water; ethyl acetate at 30℃; for 0.5h; Inert atmosphere; | 98.8% |
With sodium dithionite In diethyl ether; dichloromethane; water at 20℃; for 0.25h; Solvent; Temperature; | 68% |
5-hydroxynaphtho-1,4-quinone
benzyl bromide
5-(benzyloxy)-1,4-dihydronaphthalene-1,4-dione
Conditions | Yield |
---|---|
With silver(l) oxide In chloroform at 20℃; for 24h; | 99% |
With silver(l) oxide In chloroform | 90% |
With silver(l) oxide In chloroform for 2h; | 80% |
With silver(II) oxide In dichloromethane | 65% |
With silver(l) oxide In chloroform |
5-hydroxynaphtho-1,4-quinone
ethyl iodide
5-ethoxy-1,4-dihydronaphthalene-1,4-dione
Conditions | Yield |
---|---|
With silver(l) oxide In dichloromethane at 20℃; for 20h; Green chemistry; regioselective reaction; | 99% |
With silver(l) oxide In chloroform at 20℃; for 24h; | 97% |
Stage #1: 5-hydroxynaphtho-1,4-quinone With potassium carbonate In acetone at 20℃; for 0.0833333h; Stage #2: ethyl iodide In acetone at 80℃; for 1h; | 88% |
Conditions | Yield |
---|---|
With triethylamine at 120℃; for 0.5h; | 98% |
With sulfuric acid for 0.25h; Cooling with ice; | 93% |
With sulfuric acid for 2h; Cooling with ice; | 91% |
5-hydroxynaphtho-1,4-quinone
(S)-(E)-1-(O-methylmandeloxy)butadiene
(S)-Methoxy-phenyl-acetic acid (1R,4aS,9aS)-8-hydroxy-9,10-dioxo-1,4,4a,9,9a,10-hexahydro-anthracen-1-yl ester
Conditions | Yield |
---|---|
With triacetoxyborane In chloroform 1.) 0 deg C, 2.) room temperature; | 98% |
Conditions | Yield |
---|---|
Stage #1: 5-hydroxynaphtho-1,4-quinone With triethylamine In diethyl ether at 20℃; for 0.5h; Stage #2: tetradecanoyl chloride In diethyl ether at 20℃; for 1h; | 98% |
With triethylamine In benzene Heating; | |
With dmap In dichloromethane at 0 - 20℃; |
(Z)-9-octadecenoyl chloride
5-hydroxynaphtho-1,4-quinone
5-{(Z)-octadec-9-enoyloxy}-1,4-naphthoquinone
Conditions | Yield |
---|---|
Stage #1: 5-hydroxynaphtho-1,4-quinone With triethylamine In diethyl ether at 20℃; for 0.5h; Stage #2: (Z)-9-octadecenoyl chloride In diethyl ether at 20℃; for 1h; | 98% |
With pyridine; dmap at 20℃; for 3h; |
n-dodecanoyl chloride
5-hydroxynaphtho-1,4-quinone
5-O-dodecanoyloxy-1,4-naphthoquinone
Conditions | Yield |
---|---|
Stage #1: 5-hydroxynaphtho-1,4-quinone With triethylamine In diethyl ether at 20℃; for 0.5h; Stage #2: n-dodecanoyl chloride In diethyl ether at 20℃; for 1h; | 98% |
With dmap In dichloromethane at 0 - 20℃; |
5-hydroxynaphtho-1,4-quinone
2-amino-8-hydroxy-naphthalene-1,4-dione
Conditions | Yield |
---|---|
With hydrogenchloride; sodium azide In methanol; water for 6h; Ambient temperature; | 97% |
With hydrogenchloride; sodium azide In methanol; water at 30 - 35℃; for 22h; pH=4; Inert atmosphere; | 94% |
With trimethylsilylazide; triethylamine In N,N-dimethyl-formamide for 1h; Ambient temperature; | 91% |
1-acetoxy-1,3-butadiene
5-hydroxynaphtho-1,4-quinone
1-acetoxy-8-hydroxy-9,10-dioxo-1,4,4a,9,9a,10-hexahydroanthracene
Conditions | Yield |
---|---|
96.8% |
5-hydroxynaphtho-1,4-quinone
iodomethylbenzene
5-(benzyloxy)-1,4-dihydronaphthalene-1,4-dione
Conditions | Yield |
---|---|
With silver(l) oxide In chloroform Heating; | 96% |
5-hydroxynaphtho-1,4-quinone
Stearoyl chloride
5-O-octadecanoyloxy-1,4-naphthoquinone
Conditions | Yield |
---|---|
Stage #1: 5-hydroxynaphtho-1,4-quinone With triethylamine In diethyl ether at 20℃; for 0.5h; Stage #2: Stearoyl chloride In diethyl ether at 20℃; for 1h; | 96% |
With pyridine; dmap at 20℃; for 3h; |
Conditions | Yield |
---|---|
Stage #1: 5-hydroxynaphtho-1,4-quinone With triethylamine In diethyl ether at 20℃; for 0.5h; Stage #2: n-hexadecanoyl chloride In diethyl ether at 20℃; for 1h; | 96% |
With dmap In dichloromethane at 0 - 20℃; | 49% |
5-hydroxynaphtho-1,4-quinone
3-chlorojuglone
Conditions | Yield |
---|---|
With iodine; mercury dichloride; copper dichloride In acetic acid at 60℃; for 3h; | 95% |
Stage #1: 5-hydroxynaphtho-1,4-quinone With chlorine; acetic acid at 20℃; for 0.5h; Stage #2: In ethanol for 0.25h; Heating; | 85% |
Stage #1: 5-hydroxynaphtho-1,4-quinone With chlorine In acetic acid for 0.5h; Stage #2: With ethanol for 0.5h; Reflux; | 56% |
5-hydroxynaphtho-1,4-quinone
2-bromo-5-hydroxy-[1,4]naphthoquinone
Conditions | Yield |
---|---|
With trichloro(N,N'-ethylene-bis-aminobenzamide)lanthanum(III); bromine In tetrachloromethane at 50℃; for 0.416667h; further reagent: trichloro(N,N'-ethylene-bis-aminobenzamide)samarium(III); | 95% |
With aluminum oxide; bromine for 1.5h; Ambient temperature; other reagents: iodine monobromide, acetic acid; | 94% |
With copper(II) bromide supported on alumina In various solvent(s) at 128℃; for 42h; | 40% |
With bromine In chloroform for 0.233333h; |
5-hydroxynaphtho-1,4-quinone
cyclopenta-1,3-diene
(1R*,4S*,4aR*,9aS*)-1,4,4a,9a-tetrahydro-5-hydroxy-1,4-methano-anthracene-9,10-quinone
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 2h; Diels-Alder reaction; | 95% |
In benzene for 1h; Heating; | 75% |
5-hydroxynaphtho-1,4-quinone
N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide
Conditions | Yield |
---|---|
With tert-butyldimethylsilyl chloride In acetonitrile at 60℃; for 0.5h; | 95% |
Conditions | Yield |
---|---|
Stage #1: 5-hydroxynaphtho-1,4-quinone With dimethyl amine In water for 1h; Stage #2: With hydrogenchloride; water for 24h; Reflux; | 95% |
Multi-step reaction with 2 steps 1: 20 percent / 30percent H2O2, K / toluene / 0.25 h / Ambient temperature 2: ccHCl View Scheme | |
Multi-step reaction with 2 steps 1: 30 percent / H2O / Ambient temperature 2: 90 percent / cond. HCl View Scheme | |
Multi-step reaction with 2 steps 1: dodecatungstosilic acid / 48 h / 20 °C 2: potassium hydroxide / methanol / 6 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: toluene; tetrahydrofuran / 24 h / -20 °C 2: hydrogenchloride; water / 1,4-dioxane / 5 h / Reflux View Scheme |
5-hydroxynaphtho-1,4-quinone
Ni(C10H5O3)2(H2O)2
Conditions | Yield |
---|---|
With NH3 In ethanol; water to aq. soln. Ni(OAc)2*H2O soln. 5-HNQ in boiling ethanol added slowly with stirring, pH adjusted to 5 with 25% NH3 and mixt. left stirring at room temp. for 3 h and kept in refrigerator overnight; ppt. washed with warm water, ethanol, diethyl ether and dried in vac. desiccator over P2O5; elem. anal.; | 95% |
Conditions | Yield |
---|---|
Stage #1: 5-hydroxynaphtho-1,4-quinone; acetyl chloride With dmap In dichloromethane at 20℃; for 1h; Stage #2: With triethylamine In dichloromethane | 95% |
5-hydroxynaphtho-1,4-quinone
(-)-{1-(R)-[(1E)-2-methylbuta-1,3-dienyloxy]ethyl}benzene
1,4,4a,9a-Tetrahydro-8-hydroxy-2-methyl-1-(1-phenylethoxy)-9,10-anthraquinone
Conditions | Yield |
---|---|
In toluene Heating; | 93% |
Conditions | Yield |
---|---|
With sulfuric acid In acetic acid at 20℃; under 760.051 Torr; for 2h; Inert atmosphere; | 93% |
5-hydroxynaphtho-1,4-quinone
chloromethyl methyl ether
5-(methoxymethoxy)-1,4-naphthoquinone
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 25℃; Substitution; | 92% |
With N-ethyl-N,N-diisopropylamine In dichloromethane for 14.25h; Inert atmosphere; | 92% |
With sodium hydride In tetrahydrofuran at 25℃; for 18h; | 85% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 16h; Green chemistry; regioselective reaction; | 79% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 3h; |
Chemistry informtion about 5-Hydroxy-1,4-naphthalenedione (CAS NO.481-39-0) is:
IUPAC Name: 5-Hydroxynaphthalene-1,4-dione
Synonyms: 1,4-Naphthalenedione,5-hydroxy- ; 1,4-Naphthoquinone, 5-hydroxy- ; 1,4-Naphthoquinone, 8-hydroxy- ; 4-Naphthalenedione,5-hydroxy-1 ; 5-Hydroxy-1,4-naftochinon ; 5-hydroxy-4-naphthalenedione ; 5-hydroxy-4-naphthoquinone ; 5-Hydroxynaphthoquinone
MF: C10H6O3
MW: 174.15
EINECS: 207-567-5
Melting Point: 161-163 °C(lit.)
Density: 1.439 g/cm3
Flash Point: 201.3 °C
Boiling Point: 385.8 °C at 760 mmHg
Vapour Pressure: 1.67E-06 mmHg at 25°C
Enthalpy of Vaporization: 65.95 kJ/mol
Water Solubility: Soluble in hot water
Storage temp.: Refrigerator (+4°C)
Merck: 5269
Following is the molecular structure of 5-Hydroxy-1,4-naphthalenedione (CAS NO.481-39-0) is:
Raw materials: N-Hydroxyphthalimide
1. | hma-mus/ast 10 mg/kg | PSEBAA Proceedings of the Society for Experimental Biology and Medicine. 126 (1967),583. | ||
2. | skn-mus TDLo:394 mg/kg/53W-I:NEO | JMCMAR Journal of Medicinal Chemistry. 21 (1978),26. | ||
3. | orl-mus LD50:2500 µg/kg | SCIEAS Science. 134 (1961),1617. |
Poison by ingestion. Questionable carcinogen with experimental neoplastigenic data. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes:
T: Toxic
Risk Statements:
R25: Toxic if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements:
S22: Do not breathe dust.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S37/39: Wear suitable gloves and eye/face protection.
S28A: After contact with skin, wash immediately with plenty of water.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: QJ5775000
HazardClass: 6.1
PackingGroup: III
5-Hydroxy-1,4-naphthalenedione (CAS NO.481-39-0) is a oange to brown crystalline powder.It i insoluble in water.
First Aid Measures:
Ingestion: Never give anything by mouth to an unconscious person. Get medical aid immediately. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation: Get medical aid immediately. Remove from exposure to fresh air immediately. If breathing is difficult, give oxygen. Do not use mouth-to-mouth respiration if victim ingested or inhaled the substance; induce artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device.
Skin: Get medical aid. Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Handling and Storage:
Storage:Store in a tightly closed container. Store in a cool, dry area away from incompatible substances.
Handling: Wash thoroughly after handling. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Do not ingest or inhale. Use only in a chemical fume hood.
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