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inquiry1,2-Dihydroxy-9,10-anthracenedione 72-48-0 1,2-Dihydroxy-9,10-anthracenedione Basic information Product Name: 1,2-Dihydroxy-9,10-anthracenedione Synonyms: 1,2-Dihydroxy-anthrachinon;1,
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inquirySuperior quality, moderate price & quick delivery. Appearance:orange powder Storage:Stored in cool, dry and ventilation place; Away from fire and heat Package:25kg/drum, or as per your request. Application:Used as Pharmaceutical Intermediates T
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inquiryConditions | Yield |
---|---|
With aluminium trichloride In nitrobenzene at 80℃; for 0.25h; | 60% |
With aluminium trichloride; C6H4NO2 at 165℃; for 4h; Fridel-Crafts acylation; |
Conditions | Yield |
---|---|
With aluminium trichloride; sodium chloride at 165℃; for 4h; Fridel-Crafts acylation; | 55% |
Stage #1: phthalic anhydride; benzene-1,2-diol With aluminum (III) chloride; sodium chloride at 110 - 165℃; for 4h; Friedel Crafts Acylation; Stage #2: With hydrogenchloride In water at 0 - 100℃; for 0.75h; Heating / reflux; | 55% |
Stage #1: phthalic anhydride; benzene-1,2-diol With aluminum (III) chloride; sodium chloride at 110 - 165℃; for 4h; Friedel-Crafts Acylation; Stage #2: With hydrogenchloride In water at 20 - 100℃; for 0.75h; | 36% |
1-nitroanthraquinone
A
1-hydroxyanthraquinone
B
1,4-dihydroxy-9,10-anthracenedione
C
1,2-dihydroxy-9,10-anthracenedione
Conditions | Yield |
---|---|
With potassium hydroxide; Cumene hydroperoxide In dimethyl sulfoxide at 15 - 25℃; for 10h; | A 55% B 13% C 32% |
With Cumene hydroperoxide; potassium tert-butylate In N,N,N,N,N,N-hexamethylphosphoric triamide at 15 - 20℃; for 3h; | A 45% B 8% C 35% |
2-aminoanthraquinone
A
1,2-dihydroxy-9,10-anthracenedione
B
6,15-dihydroanthrazine-5,9,14,18-tetrone
C
16-hydroxy-8,17-dihydrodinaphtho<2,3-a:2',3'-i>phenazine-5,10,15,18-tetrone
Conditions | Yield |
---|---|
With potassium hydroxide; potassium chlorate In various solvent(s) at 168 - 172℃; for 2h; | A n/a B 48% C n/a |
With potassium hydroxide; potassium chlorate In 2-ethoxy-ethanol at 168 - 172℃; for 2h; Product distribution; further solvents and oxidants; |
tetrachloromethane
2,3-dichloro-anthraquinone
1,2-dihydroxy-9,10-anthracenedione
Conditions | Yield |
---|---|
beim Schmelzen; |
phthalic anhydride
benzo-1,4-dioxane
A
hystazarin
B
1,2-dihydroxy-9,10-anthracenedione
Conditions | Yield |
---|---|
With aluminium trichloride; sodium chloride at 130 - 140℃; | |
With aluminium trichloride; sodium chloride at 170 - 180℃; |
Conditions | Yield |
---|---|
With aluminium trichloride; sodium chloride at 130 - 140℃; | |
With aluminium trichloride; sodium chloride at 170 - 180℃; |
Conditions | Yield |
---|---|
With sulfuric acid; boric acid at 240 - 255℃; |
phthalic anhydride
benzene-1,2-diol
A
hystazarin
B
1,2-dihydroxy-9,10-anthracenedione
Conditions | Yield |
---|---|
With Japanese acid earth | |
With sulfuric acid at 180 - 200℃; | |
With aluminium trichloride; sulfuric acid; sodium chloride 1.) reflux, 2 h, 2.) reflux, 3 h; Multistep reaction. Title compound not separated from byproducts; |
2-(3,4-dimethoxybenzoyl)benzoic acid
A
hystazarin
B
1,2-dihydroxy-9,10-anthracenedione
Conditions | Yield |
---|---|
With sulfuric acid at 100℃; Verseifen den Hystazarindimethylaether mit konz.Schwefelsaeure auf 200-205grad; |
3,4-dimethoxyphthalic anhydride
benzene
1,2-dihydroxy-9,10-anthracenedione
Conditions | Yield |
---|---|
With aluminium trichloride Erwaermen des Reaktionsprodukts mit konz.Schwefelsaeure auf 100grad,und nachfolgend verseifen mit Jodwasserstoffsaeure; |
1-methyl-4-nitrosobenzene
A
2-hydroxy-9,10-anthraquinone
B
1,2-dihydroxy-9,10-anthracenedione
Conditions | Yield |
---|---|
at 215℃; und Leiten von Luft durch die Reaktionsloesung; |
Conditions | Yield |
---|---|
With potassium carbonate durch Schmelzen; | |
Multi-step reaction with 2 steps 1: aqueous ammonia / 150 °C 2: NaNO2; concentrated sulfuric acid / 190 °C View Scheme |
Conditions | Yield |
---|---|
With potassium carbonate durch Schmelzen; |
Conditions | Yield |
---|---|
With potassium carbonate durch Schmelzen; |
Conditions | Yield |
---|---|
With sodium hydroxide; methyllithium; nitric acid; calcium carbonate at 200℃; Reagens 4: Na2SO3; |
2-chloro-1-hydroxy-anthraquinone
1,2-dihydroxy-9,10-anthracenedione
Conditions | Yield |
---|---|
bei der Kalischmelze; |
Conditions | Yield |
---|---|
With sodium chlorate; sodium hydroxide technische Darstellung durch Schmelzen; |
2-bromoanthracene-9,10-dione
A
2-hydroxy-9,10-anthraquinone
B
1,2-dihydroxy-9,10-anthracenedione
Conditions | Yield |
---|---|
With potassium hydroxide |
Conditions | Yield |
---|---|
With potassium hydroxide | |
With sodium hydroxide |
Conditions | Yield |
---|---|
With potassium hydroxide bei Schmelzen; | |
With sodium hydroxide bei Schmelzen; | |
in der Kalischmelze; |
Conditions | Yield |
---|---|
With sodium amalgam |
2-phenylaminoanthraquinone
A
1,2-dihydroxy-9,10-anthracenedione
B
1-Hydroxy-2-phenylaminoanthraquinone
Conditions | Yield |
---|---|
With potassium hydroxide; potassium acetate; potassium nitrate weiteres Reagens: H2O; |
Conditions | Yield |
---|---|
With sodium hydroxide | |
durch Kalischmelze; | |
With potassium hydroxide |
2-sulfo-anthraquinone
A
2-hydroxy-9,10-anthraquinone
B
1,2-dihydroxy-9,10-anthracenedione
Conditions | Yield |
---|---|
With potassium hydroxide |
Conditions | Yield |
---|---|
With alkali anschliessendes Oxydation des gebildeten 2-Oxy-anthrachinons mit Luft; | |
With potassium chlorate anschliessendes Oxydation des gebildeten 2-Oxy-anthrachinons mit Luft; |
1,2-dihydroxy-9,10-anthracenedione
propynoic acid ethyl ester
ethyl 6,11-dihydro-6,11-dioxoanthra[1,2-d][1,3]-dioxole-2-acetate
Conditions | Yield |
---|---|
With triphenylphosphine In toluene for 24h; Reflux; | 97% |
Cyclohexyl isocyanide
1,2-dihydroxy-9,10-anthracenedione
acetylenedicarboxylic acid diethyl ester
Conditions | Yield |
---|---|
In toluene for 24h; Reflux; | 97% |
1,2-dihydroxy-9,10-anthracenedione
1,1,3,3-tetramethylbutane isonitrile
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
In toluene for 24h; Reflux; | 96% |
1,2-dihydroxy-9,10-anthracenedione
benzoyl chloride
1,2-dibenzoyloxy-9,10-anthraquinone
Conditions | Yield |
---|---|
for 0.5h; Heating; | 95% |
With pyridine | |
at 190℃; |
1,2-dihydroxy-9,10-anthracenedione
dimethyl acetylenedicarboxylate
methyl 6,11-dihydro-12-hydroxy-2,6,11-trioxo-2H-naphtho[2,3-g]chromene-4-carboxylate
Conditions | Yield |
---|---|
With triphenylphosphine In toluene for 24h; Reflux; | 95% |
Cyclohexyl isocyanide
1,2-dihydroxy-9,10-anthracenedione
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
In toluene for 24h; Reflux; | 95% |
1,2-dihydroxy-9,10-anthracenedione
1,1,3,3-tetramethylbutane isonitrile
acetylenedicarboxylic acid diethyl ester
Conditions | Yield |
---|---|
In toluene for 24h; Reflux; | 95% |
1,2-dihydroxy-9,10-anthracenedione
acetylenedicarboxylic acid diethyl ester
ethyl 6,11-dihydro-12-hydroxy-2,6,11-trioxo-2H-naphtho[2,3-g]chromene-4-carboxylate
Conditions | Yield |
---|---|
With triphenylphosphine In toluene for 24h; Reflux; | 94% |
potassium tetrachloropalladate(II)
1,2-dihydroxy-9,10-anthracenedione
[C6H4(CO)2C6H2O(OH)]2Pd
Conditions | Yield |
---|---|
With potassium hydroxide In water alizarin dissolved in boiling water with equimolar amount of KOH, K2PdCl4 added, pptd., suspn. standed overnight, cooled; ppt. filtered, washed (dilute HCl soln., water, acetone, ether), dried (air) elem. anal.; | 93% |
In N,N-dimethyl-formamide byproducts: KCl; mixed, suspn. stirred at 90°C, cooled, KCl filtered off; solv. removed (vac.), washed (ether), elem. anal., IR; | 83% |
1,2-dihydroxy-9,10-anthracenedione
1-Bromooctadecane
1,2-bis[octadecyloxy]anthraquinone
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl acetamide; water | 93% |
Stage #1: 1,2-dihydroxy-9,10-anthracenedione With potassium carbonate In ISOPROPYLAMIDE at 80℃; for 1h; Stage #2: 1-Bromooctadecane In ISOPROPYLAMIDE for 7h; | 93% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; | 93% |
1,2-dihydroxy-9,10-anthracenedione
N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide
Conditions | Yield |
---|---|
With tert-butyldimethylsilyl chloride In acetonitrile at 70℃; for 0.25h; silylation; | 92% |
Conditions | Yield |
---|---|
With sulfuric acid In methanol for 48h; Heating; | 92% |
Conditions | Yield |
---|---|
With sulfuric acid In ethanol at 60℃; for 2h; Product distribution / selectivity; | 92% |
With sulfuric acid In methanol at 50℃; for 48h; Product distribution / selectivity; Heating / reflux; | 92% |
1,2-dihydroxy-9,10-anthracenedione
methyl iodide
1-hydroxy-2-methoxyanthraquinone
Conditions | Yield |
---|---|
With lithium carbonate In N,N-dimethyl-formamide at 60℃; for 24h; | 90% |
With sodium hydroxide In N,N-dimethyl-formamide at 60℃; for 24h; | 28% |
With potassium carbonate | |
With water; barium(II) oxide In N,N-dimethyl-formamide | |
With sodium hydroxide In N,N-dimethyl-formamide |
1,2-dihydroxy-9,10-anthracenedione
5-methyl-o-tolyl isocyanide
acetylenedicarboxylic acid diethyl ester
Conditions | Yield |
---|---|
In toluene for 24h; Reflux; | 90% |
Conditions | Yield |
---|---|
With tetrachlorosilane at 75℃; for 20h; Inert atmosphere; Schlenk technique; | 90% |
1,2-dihydroxy-9,10-anthracenedione
5-methyl-o-tolyl isocyanide
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
In toluene for 24h; Reflux; | 88% |
dichloro(2-anilinopyridyl-kappa.N,C)gold
1,2-dihydroxy-9,10-anthracenedione
Conditions | Yield |
---|---|
With trimethylamine In methanol for 0.333333h; Reflux; | 87% |
Conditions | Yield |
---|---|
In methanol refluxing alizarin and Bu2SnO in MeOH for 3 h; elem. anal.; | 86% |
Conditions | Yield |
---|---|
Stage #1: cisplatin With silver nitrate In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; Stage #2: 1,2-dihydroxy-9,10-anthracenedione With sodium hydroxide In water; N,N-dimethyl-formamide at 20℃; for 5h; Inert atmosphere; | 85% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 12h; Heating; | 84% |
With potassium carbonate In dimethyl sulfoxide; butanone for 15h; Reflux; | 42% |
1,2-dihydroxy-9,10-anthracenedione
di(n-butyl)tin oxide
dimethyl sulfoxide
[Bu2Sn(1,2-dihydroxyanthraquinone(-2H))(dmso)]2
Conditions | Yield |
---|---|
In chloroform; dimethyl sulfoxide refluxing alizarin and Bu2SnO in DMSO/CHCl3 for 6 h; slow evapn. of CHCl3; elem. anal.; | 83% |
1,2-dihydroxy-9,10-anthracenedione
bromoacetic acid
1-hydroxyanthracene-9,10-dione-2-yl 2-bromoacetate
Conditions | Yield |
---|---|
Stage #1: bromoacetic acid With dmap In dimethyl sulfoxide at 20℃; for 0.0833333h; Stage #2: With dicyclohexyl-carbodiimide In dimethyl sulfoxide for 0.166667h; Stage #3: 1,2-dihydroxy-9,10-anthracenedione In dimethyl sulfoxide for 4h; | 82% |
trifluoromethylsulfonic anhydride
1,2-dihydroxy-9,10-anthracenedione
1,2-bis[(trifluoromethylsulfonyl)oxy]anthraquinone
Conditions | Yield |
---|---|
Stage #1: 1,2-dihydroxy-9,10-anthracenedione With pyridine In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at -78 - 20℃; for 14h; Inert atmosphere; | 81% |
With pyridine In dichloromethane at -78 - 20℃; for 14h; Inert atmosphere; | 81% |
1,2-dihydroxy-9,10-anthracenedione
2-Bromopropionic acid
1-hydroxyanthracene-9,10-dione-2-yl 2-bromopropionate
Conditions | Yield |
---|---|
Stage #1: 2-Bromopropionic acid With dmap In dimethyl sulfoxide at 20℃; for 0.0833333h; Stage #2: With dicyclohexyl-carbodiimide In dimethyl sulfoxide for 0.166667h; Stage #3: 1,2-dihydroxy-9,10-anthracenedione In dimethyl sulfoxide for 4h; | 80% |
dodecacarbonyl-triangulo-triruthenium
tributylphosphine
1,2-dihydroxy-9,10-anthracenedione
1,2-bis-(diphenylphosphino)ethane
Conditions | Yield |
---|---|
In toluene soln. of Ru-complex, dppe, and ligand in toluene was heated at reflux under Ar for 4 h, PBu3 was added, refluxed for 6 h; evapd. to dryness, recrystd. from CH2Cl2/MeOH; elem. anal.; | 79% |
1,2-dihydroxy-9,10-anthracenedione
1-bromoacetone
1-hydroxy-2-acetonyloxyanthraquinone
Conditions | Yield |
---|---|
With potassium carbonate In acetone Reflux; | 79% |
(CH3CO2CH2CH2)2SnCl2
1,2-dihydroxy-9,10-anthracenedione
(CH3OCOCH2CH2)2Sn(C14H6O4)
Conditions | Yield |
---|---|
With ammonia In methanol byproducts: NH4Cl; heated on a water bath, ammonia soln. was added; filtered, refluxed for 1 h, recrystd. from chloroform/methanol; elem. anal.; | 78% |
Conditions | Yield |
---|---|
Stage #1: 1-methyl-piperazine; formaldehyd With hydrogenchloride In ethanol at 80℃; for 2h; Stage #2: 1,2-dihydroxy-9,10-anthracenedione In ethanol at 80℃; for 10.5h; Inert atmosphere; | 78% |
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