Product Name

  • Name

    5-Hydroxy-1,4-naphthalenedione

  • EINECS 207-567-5
  • CAS No. 481-39-0
  • Article Data50
  • CAS DataBase
  • Density 1.439 g/cm3
  • Solubility soluble in hot water
  • Melting Point 161-163 °C(lit.)
  • Formula C10H6O3
  • Boiling Point 385.8 °C at 760 mmHg
  • Molecular Weight 174.156
  • Flash Point 201.3 °C
  • Transport Information UN 2811 6.1/PG 3
  • Appearance Orange to brown crystalline powder
  • Safety 22-26-36/37/39-45-37/39
  • Risk Codes 25-36/37/38
  • Molecular Structure Molecular Structure of 481-39-0 (5-Hydroxy-1,4-naphthalenedione)
  • Hazard Symbols ToxicT
  • Synonyms Juglone (6CI);1,4-Dihydro-1,4-dioxo-5-hydroxynaphthalene;8-Hydroxy-1,4-naphthoquinone;Akhnot;C.I. 75500;C.I.Natural Brown 7;NSC 153189;Natural Brown 7;
  • PSA 54.37000
  • LogP 1.32740

Synthetic route

1,5-dihydroxynaphthalene
83-56-7

1,5-dihydroxynaphthalene

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

Conditions
ConditionsYield
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%
juglone acetate
5196-28-1

juglone acetate

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

Conditions
ConditionsYield
With water; trifluoroacetic acid at 72℃; for 0.75h;95%
1,8-dihydroxynaphthalene
569-42-6

1,8-dihydroxynaphthalene

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

Conditions
ConditionsYield
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
130-15-4

[1,4]naphthoquinone

A

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

B

5,8-Dihydroxy-1,4-naphthoquinone
475-38-7

5,8-Dihydroxy-1,4-naphthoquinone

Conditions
ConditionsYield
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
83-56-7

1,5-dihydroxynaphthalene

A

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

B

5-hydroxy-1,2-naphthoquinone
38028-39-6

5-hydroxy-1,2-naphthoquinone

Conditions
ConditionsYield
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%
5-methoxynaphthoquinone
4923-61-9

5-methoxynaphthoquinone

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 20℃;81%
2-Methyl-1,5-naphthalindiol-5-acetat
116752-27-3

2-Methyl-1,5-naphthalindiol-5-acetat

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

Conditions
ConditionsYield
With oxygen; methylene blue In acetonitrile at 20℃; for 4h; Irradiation;78%
5-hydroxynaphthalen-1-yl acetate
94807-85-9

5-hydroxynaphthalen-1-yl acetate

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

Conditions
ConditionsYield
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%
2,5-dihydroxy-2,3-dihydrobenzofuran
1012-98-2

2,5-dihydroxy-2,3-dihydrobenzofuran

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

Conditions
ConditionsYield
With dihydrogen peroxide62%
3-hydroxy-2-pyrone
496-64-0

3-hydroxy-2-pyrone

p-benzoquinone
106-51-4

p-benzoquinone

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

Conditions
ConditionsYield
With triethylamine In chloroform at -20℃; for 0.5h; Diels-Alder reaction;60%
2,3,4,5,6-pentafluoroaniline
771-60-8

2,3,4,5,6-pentafluoroaniline

1,5-dihydroxynaphthalene
83-56-7

1,5-dihydroxynaphthalene

A

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

B

5-hydroxy-4-pentafluorophenylimino-4H-naphthalen-1-one

5-hydroxy-4-pentafluorophenylimino-4H-naphthalen-1-one

Conditions
ConditionsYield
With iodic acid In ethanol; water at 20℃; for 2h;A 25%
B 45%
2,5-dihydroxy-2,3-dihydrobenzofuran
1012-98-2

2,5-dihydroxy-2,3-dihydrobenzofuran

A

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

B

juglone
6312-53-4

juglone

Conditions
ConditionsYield
With acidA 15%
B 44%
2,3-epoxy-5-hydroxy-2,3-dihydro-1,4-naphthoquinone
15255-29-5

2,3-epoxy-5-hydroxy-2,3-dihydro-1,4-naphthoquinone

A

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

B

3,5-dihydroxy-2,3-dihydro-1,4-naphthoquinone
4923-58-4

3,5-dihydroxy-2,3-dihydro-1,4-naphthoquinone

C

2-Hydroxyjuglon
4923-55-1

2-Hydroxyjuglon

Conditions
ConditionsYield
With sodium acetate; acetic acid; sodium iodide; zinc for 1.5h; Ambient temperature;A 33%
B n/a
C n/a
C31H26O9
80781-03-9

C31H26O9

A

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

B

1,8-dihydroxy-11-methoxy-7,8,9,10-tetrahydronaphthacece-5,12-dione
80781-02-8

1,8-dihydroxy-11-methoxy-7,8,9,10-tetrahydronaphthacece-5,12-dione

Conditions
ConditionsYield
With base In methanolA n/a
B 7%
1,4,5-trihydroxynaphthalene
481-40-3

1,4,5-trihydroxynaphthalene

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

Conditions
ConditionsYield
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
5,8-dihydroxy-1-tetralone
1077-69-6

5,8-dihydroxy-1-tetralone

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

Conditions
ConditionsYield
With iron(III) chloride; acetic acid
[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

Conditions
ConditionsYield
With diacetylnitric acid
5-methoxynaphthalen-1-ol
3588-80-5

5-methoxynaphthalen-1-ol

A

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

B

5-methoxynaphthoquinone
4923-61-9

5-methoxynaphthoquinone

C

8-Hydroxy-4-methoxy-1,2-naphthochinon
101303-83-7

8-Hydroxy-4-methoxy-1,2-naphthochinon

Conditions
ConditionsYield
With oxygen; methylene blue In methanol at 22℃; for 12h; Irradiation;
1,8-dihydroxynaphthalene
569-42-6

1,8-dihydroxynaphthalene

A

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

B

8,8'-bijuglone
101459-03-4

8,8'-bijuglone

Conditions
ConditionsYield
Product distribution; oxidation;
5-amino-8-hydroxy-[1,4]naphthoquinone
68217-36-7

5-amino-8-hydroxy-[1,4]naphthoquinone

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

Conditions
ConditionsYield
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
97308-88-8

5-Methoxy-1-methylbenzindazol-4,9-chinon

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

Conditions
ConditionsYield
With aluminium trichloride In chloroform Heating;
(-)-(4S)-4,8-dihydroxy-α-tetralone
54712-38-8, 51114-98-8, 62332-73-4, 137494-04-3

(-)-(4S)-4,8-dihydroxy-α-tetralone

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 8h; Heating;10 mg
β-hydrojuglone

β-hydrojuglone

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

Conditions
ConditionsYield
With ethanol; iron(III) chloride nach vorhergegangener Bildung von α-Hydrojuglon;
1,4-diamino-<5>naphthol

1,4-diamino-<5>naphthol

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

Conditions
ConditionsYield
With water; iron(III) chloride
1-oxy-8-amino-naphthalene

1-oxy-8-amino-naphthalene

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

Conditions
ConditionsYield
With 4-sulfobenzenediazonium Reduzieren des Gebildeten Azofarbstoffs mit Zn und HCl und Oxidieren des Reduktionsprodukts mit FeCl3;
4-amino-naphthalenediol-(1.5)-hydrochloride

4-amino-naphthalenediol-(1.5)-hydrochloride

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

Conditions
ConditionsYield
With hydrogenchloride; iron(III) chloride
1,8-dihydroxynaphthalene
569-42-6

1,8-dihydroxynaphthalene

chromic acid mixture

chromic acid mixture

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

1,4,5-trihydroxynaphthalene
481-40-3

1,4,5-trihydroxynaphthalene

bromine
7726-95-6

bromine

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

1,4,5-trihydroxynaphthalene
481-40-3

1,4,5-trihydroxynaphthalene

iron(III) chloride
7705-08-0

iron(III) chloride

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

methyl iodide
74-88-4

methyl iodide

5-methoxynaphthoquinone
4923-61-9

5-methoxynaphthoquinone

Conditions
ConditionsYield
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
75-30-9

2-iodo-propane

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

5-isopropoxy-1,4-naphthoquinone
97308-90-2

5-isopropoxy-1,4-naphthoquinone

Conditions
ConditionsYield
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
481-39-0

5-hydroxynaphtho-1,4-quinone

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

(1R*,4S*,4aR*,9aS*)-1,4,4a,9a-tetrahydro-5-hydroxy-1,4-methano-9,10-anthracenedione
163180-66-3

(1R*,4S*,4aR*,9aS*)-1,4,4a,9a-tetrahydro-5-hydroxy-1,4-methano-9,10-anthracenedione

Conditions
ConditionsYield
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;
2-Fluoroaniline
348-54-9

2-Fluoroaniline

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

2-(2-fluoroanilino)-5-hydroxy-1,4-naphthoquinone

2-(2-fluoroanilino)-5-hydroxy-1,4-naphthoquinone

Conditions
ConditionsYield
Stage #1: 5-hydroxynaphtho-1,4-quinone In ethanol for 0.25h;
Stage #2: 2-Fluoroaniline In ethanol for 4h; Reflux;
100%
5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

1,4,5-trihydroxynaphthalene
481-40-3

1,4,5-trihydroxynaphthalene

Conditions
ConditionsYield
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
481-39-0

5-hydroxynaphtho-1,4-quinone

benzyl bromide
100-39-0

benzyl bromide

5-(benzyloxy)-1,4-dihydronaphthalene-1,4-dione
75445-61-3

5-(benzyloxy)-1,4-dihydronaphthalene-1,4-dione

Conditions
ConditionsYield
With silver(l) oxide In chloroform at 20℃; for 24h;99%
With silver(l) oxide In chloroform90%
With silver(l) oxide In chloroform for 2h;80%
With silver(II) oxide In dichloromethane65%
With silver(l) oxide In chloroform
5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

ethyl iodide
75-03-6

ethyl iodide

5-ethoxy-1,4-dihydronaphthalene-1,4-dione
22924-19-2

5-ethoxy-1,4-dihydronaphthalene-1,4-dione

Conditions
ConditionsYield
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%
5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

acetic anhydride
108-24-7

acetic anhydride

juglone acetate
5196-28-1

juglone acetate

Conditions
ConditionsYield
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
481-39-0

5-hydroxynaphtho-1,4-quinone

(S)-(E)-1-(O-methylmandeloxy)butadiene
75909-37-4

(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
75920-38-6

(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
ConditionsYield
With triacetoxyborane In chloroform 1.) 0 deg C, 2.) room temperature;98%
5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

tetradecanoyl chloride
112-64-1

tetradecanoyl chloride

juglone myristate
64817-83-0

juglone myristate

Conditions
ConditionsYield
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
112-77-6

(Z)-9-octadecenoyl chloride

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

5-{(Z)-octadec-9-enoyloxy}-1,4-naphthoquinone
1340543-24-9

5-{(Z)-octadec-9-enoyloxy}-1,4-naphthoquinone

Conditions
ConditionsYield
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
112-16-3

n-dodecanoyl chloride

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

5-O-dodecanoyloxy-1,4-naphthoquinone
1340543-22-7

5-O-dodecanoyloxy-1,4-naphthoquinone

Conditions
ConditionsYield
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
481-39-0

5-hydroxynaphtho-1,4-quinone

2-amino-8-hydroxy-naphthalene-1,4-dione
77507-72-3

2-amino-8-hydroxy-naphthalene-1,4-dione

Conditions
ConditionsYield
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
1515-76-0

1-acetoxy-1,3-butadiene

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

1-acetoxy-8-hydroxy-9,10-dioxo-1,4,4a,9,9a,10-hexahydroanthracene
86668-63-5

1-acetoxy-8-hydroxy-9,10-dioxo-1,4,4a,9,9a,10-hexahydroanthracene

Conditions
ConditionsYield
96.8%
5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

iodomethylbenzene
620-05-3

iodomethylbenzene

5-(benzyloxy)-1,4-dihydronaphthalene-1,4-dione
75445-61-3

5-(benzyloxy)-1,4-dihydronaphthalene-1,4-dione

Conditions
ConditionsYield
With silver(l) oxide In chloroform Heating;96%
5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

Stearoyl chloride
112-76-5

Stearoyl chloride

5-O-octadecanoyloxy-1,4-naphthoquinone
1340543-23-8

5-O-octadecanoyloxy-1,4-naphthoquinone

Conditions
ConditionsYield
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;
5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

5-O-hexadecanoyloxy-1,4-naphthoquinone

5-O-hexadecanoyloxy-1,4-naphthoquinone

Conditions
ConditionsYield
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
481-39-0

5-hydroxynaphtho-1,4-quinone

3-chlorojuglone
18855-92-0

3-chlorojuglone

Conditions
ConditionsYield
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
481-39-0

5-hydroxynaphtho-1,4-quinone

2-bromo-5-hydroxy-[1,4]naphthoquinone
69008-03-3

2-bromo-5-hydroxy-[1,4]naphthoquinone

Conditions
ConditionsYield
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
481-39-0

5-hydroxynaphtho-1,4-quinone

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

(1R*,4S*,4aR*,9aS*)-1,4,4a,9a-tetrahydro-5-hydroxy-1,4-methano-anthracene-9,10-quinone
73921-57-0, 132016-32-1, 144299-62-7, 144299-64-9

(1R*,4S*,4aR*,9aS*)-1,4,4a,9a-tetrahydro-5-hydroxy-1,4-methano-anthracene-9,10-quinone

Conditions
ConditionsYield
In dichloromethane at 20℃; for 2h; Diels-Alder reaction;95%
In benzene for 1h; Heating;75%
5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide
77377-52-7

N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide

5-(dimethyl-t-butylsilyloxy)-1,4-naphthoquinone

5-(dimethyl-t-butylsilyloxy)-1,4-naphthoquinone

Conditions
ConditionsYield
With tert-butyldimethylsilyl chloride In acetonitrile at 60℃; for 0.5h;95%
5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

2-Hydroxyjuglon
4923-55-1

2-Hydroxyjuglon

Conditions
ConditionsYield
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
nickel(II) acetate hydrate

nickel(II) acetate hydrate

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

Conditions
ConditionsYield
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%
5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

acetyl chloride
75-36-5

acetyl chloride

juglone acetate
5196-28-1

juglone acetate

Conditions
ConditionsYield
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
481-39-0

5-hydroxynaphtho-1,4-quinone

(-)-{1-(R)-[(1E)-2-methylbuta-1,3-dienyloxy]ethyl}benzene
130814-75-4

(-)-{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
130814-84-5

1,4,4a,9a-Tetrahydro-8-hydroxy-2-methyl-1-(1-phenylethoxy)-9,10-anthraquinone

Conditions
ConditionsYield
In toluene Heating;93%
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

8-hydroxy-2-(2,4,6-trihydroxyphenyl)naphthalene-1,4-dione

8-hydroxy-2-(2,4,6-trihydroxyphenyl)naphthalene-1,4-dione

Conditions
ConditionsYield
With sulfuric acid In acetic acid at 20℃; under 760.051 Torr; for 2h; Inert atmosphere;93%
5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

5-(methoxymethoxy)-1,4-naphthoquinone
176040-42-9

5-(methoxymethoxy)-1,4-naphthoquinone

Conditions
ConditionsYield
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;

5-Hydroxy-1,4-naphthalenedione Chemical Properties

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:

5-Hydroxy-1,4-naphthalenedione Production

Raw materials: N-Hydroxyphthalimide

5-Hydroxy-1,4-naphthalenedione Toxicity Data With Reference

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.

5-Hydroxy-1,4-naphthalenedione Safety Profile

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 Specification

 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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