Conditions | 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% |
.
Empirical Formula: C14H8O4
Molecular Weight: 240.2109
EINECS: 200-782-5
Index of Refraction: 1.732
Molar Refractivity: 62.43 cm3
Molar Volume: 155.9 cm3
Surface Tension: 79.2 dyne/cm
Density: 1.54 g/cm3
Flash Point: 228 °C
Enthalpy of Vaporization: 71.19 kJ/mol
Boiling Point: 430 °C at 760 mmHg
Vapour Pressure: 5.34E-08 mmHg at 25 °C
Melting point: 287 °C
Appearance: Orange-red crystals or powder
Structure of 1,2-Dihydroxy-9,10-anthracenedione (CAS NO.72-48-0):
IUPAC Name: 1,2-Dihydroxyanthracene-9,10-dione
Canonical SMILES: C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C(=C(C=C3)O)O
InChI: InChI=1S/C14H8O4/c15-10-6-5-9-11(14(10)18)13(17)8-4-2-1-3-7(8)12(9)16/h1-6,15,18H
InChIKey: RGCKGOZRHPZPFP-UHFFFAOYSA-N
Product Category of 1,2-Dihydroxy-9,10-anthracenedione (CAS NO.72-48-0): Intermediates of Dyes and Pigments;Anthraquinones, Hydroquinones and Quinones;Hydroxyanthraquinones
1,2-Dihydroxy-9,10-anthracenedione (CAS NO.72-48-0) can be used as dye intermediates and acid-base indicator.
1. | eye-rbt 500 mg/24H MLD | 28ZPAK Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,101. | ||
2. | mmo-sat 100 µg/plate | MUREAV Mutation Research. 40 (1976),203. | ||
3. | mma-sat 100 µg/plate | MUREAV Mutation Research. 40 (1976),203. | ||
4. | dnr-bcs 2 mg/disc | TRENAF Kenkyu Nenpo-Tokyo-toritsu Eisei Kenkyusho. Annual Report of Tokyo Metropolitan Research Laboratory of Public Health. 27 (1976),153. | ||
5. | orl-bwd LD50:316 mg/kg | AECTCV Archives of Environmental Contamination and Toxicology. 12 (1983),355. |
Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
Poison by ingestion. Mutation data reported. An eye irritant. Flammable when exposed to oxidizers and heat. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard symbols: Xi.
Risk statements: 36/38-36/37/38.
36/38: Irritating to eyes and skin.
36/37/38: Irritating to eyes, respiratory system and skin.
Safety statements: 26-36-24/25-22.
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
36: Wear suitable protective clothing.
22: Do not breathe dust.
24/25: Avoid contact with skin and eyes.
1,2-Dihydroxy-9,10-anthracenedione , its cas register number is 72-48-0. It also can be called C.I. 58000 ; Mordant Red 11 ; 1,2-Dihydroxyanthraquinone ; Alizarin Red ; Dihydroxy-9,10-anthracenedione ; and 1,2-Dihydroxy anthraquinone . It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product: Wash mouth out with water, and get medical aid immediately. Notes to physician: Treat supportively and symptomatically.
In addition, 1,2-Dihydroxy-9,10-anthracenedione (CAS NO.72-48-0) could be stable under normal temperatures and pressures. It is not compatible with strong oxidizing agents, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: Carbon monoxide, carbon dioxide.
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