Conditions | Yield |
---|---|
With oxygen In acetone at 20℃; under 760.051 Torr; for 10h; Reagent/catalyst; Solvent; Irradiation; | 100% |
With [bis(acetoxy)iodo]benzene; tert-butyl hydroxyperoxide; 3-chloro-benzenecarboperoxoic acid In 2,2,2-trifluoroethanol at 20℃; for 9h; | 99% |
With 2-Picolinic acid; manganese(II) perchlorate hexahydrate; dihydrogen peroxide; sodium acetate In acetonitrile at 0 - 20℃; | 99% |
Conditions | Yield |
---|---|
With nicotinium dichromate In acetic acid for 0.75h; Heating; | 100% |
With potassium bromate In acetic acid Heating; | 100% |
With ruthenium trichloride; dihydrogen peroxide; acetic acid | 100% |
Conditions | Yield |
---|---|
With aluminum oxide; potassium permanganate; water In 1,2-dichloro-ethane for 75h; Ambient temperature; | 100% |
With aluminum oxide; potassium permanganate for 75h; | 100% |
With cerium(III) sulfate; barium bromate In water; acetonitrile for 20h; Heating; | 97% |
9,10-dihydro-9,10-dihydroxyanthracene
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
In neat (no solvent) at 20℃; for 0.0333333h; Microwave irradiation; | 100% |
With tert.-butylhydroperoxide; RhCl(PPh3)3 In benzene at 70℃; for 48h; | 87% |
With tert.-butylhydroperoxide; RhCl(PPh3)3 In benzene at 70℃; for 48h; | 87% |
Conditions | Yield |
---|---|
Stage #1: 9-methylsulfinyl-10-(methylthio)anthracene With air; sulfuric acid In dichloromethane at 20℃; for 0.0833333h; Rearrangement; Stage #2: With water; sodium hydrogencarbonate Hydrolysis; | A n/a B 100% |
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
With osmium(VIII) oxide; trimethylamine-N-oxide In tetrahydrofuran; pyridine; water at 65℃; | 100% |
anthracene-9-boronic acid
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
With water; sodium hydroxide In tetrahydrofuran at 20℃; for 2h; Reagent/catalyst; | 99.03% |
Conditions | Yield |
---|---|
With zinc(II) nitrate; silica gel In tetrachloromethane for 0.25h; Heating; | 98% |
With hydrogenchloride; iodosylbenzene for 0.0833333h; Oxidation; | 79% |
With air; acetic acid Irradiation; | |
With bromine | |
With iodine |
Conditions | Yield |
---|---|
With aluminum oxide; potassium permanganate In dichloromethane at 20℃; for 72h; | 98% |
Conditions | Yield |
---|---|
With oxygen; pyrographite In 5,5-dimethyl-1,3-cyclohexadiene; toluene at 120℃; under 760.051 Torr; for 48h; Schlenk technique; Cooling with ice; | 98% |
Conditions | Yield |
---|---|
With sulfuric acid at 100℃; | 97.8% |
With sulfuric acid 1.) 140-200 deg C, vacuum 100-20 mm Hg, 2.) 180-200 deg C, 10 min; | 93% |
With Nafion-H In various solvent(s) at 180℃; for 3h; Acylation; Friedel-Crafts intramolecular acylation; | 90% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide In water; N,N-dimethyl-formamide at 20 - 80℃; for 4h; Reagent/catalyst; Solvent; | 97% |
With water; potassium bromide In chloroform at 25℃; for 1.56667h; pH=12; pH-value; Electrochemical reaction; | 96% |
With 1-ethyl-2,3-dimethylimidazolium iodide; sodium hydride In tetrahydrofuran at 20℃; for 72h; | 46% |
With potassium bromate In acetic acid for 0.5h; Heating; | 80 mg |
With tetrabutylammomium bromide; oxygen In dimethylsulfoxide-d6; chloroform-d1 at 25℃; for 8h; Reagent/catalyst; Irradiation; |
N-(anthracen-9-yl)acetamide
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
With Selectfluor In methanol at 30℃; for 0.5h; | 97% |
9,10-dihydroanthracene
A
[(1,10-phenanthroline)2Mn(η1-OClO3)2]
B
anthracene
C
anthracen-9(10H)-one
D
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
In acetonitrile Kinetics; the soln. in acetonitrile was allowed to stand overnight at room temp.; the organic products were detected by GC/MS; the soln. was layered with ether; | A n/a B 97% C 0.8% D 2% |
9,10-bromoanthracene-9-carbaldehyde
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
With N-Bromosuccinimide In water; N,N-dimethyl-formamide at 20 - 80℃; for 4h; | 97% |
With water; potassium bromide In chloroform at 25℃; pH=9; Electrochemical reaction; | 95% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 1h; | 97% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 60℃; | 74% |
Conditions | Yield |
---|---|
With water; potassium bromide In chloroform at 25℃; pH=9; Electrochemical reaction; | 96% |
With air; ethanol Irradiation.Sonnenlicht; | |
With osmium(VIII) oxide In hexane at 25℃; for 4.75h; Irradiation; | |
Multi-step reaction with 3 steps 1: potassium thioacetate; potassium phosphate; bis(dibenzylideneacetone)-palladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / toluene; acetone / 48 h / Inert atmosphere; Reflux 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / Reflux 3: oxygen / 12 h / Irradiation View Scheme | |
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 - 20 °C / Inert atmosphere 1.3: Inert atmosphere 2.1: oxygen / acetonitrile / 0.5 h / Irradiation View Scheme |
Conditions | Yield |
---|---|
With N-Bromosuccinimide In water; N,N-dimethyl-formamide at 20 - 80℃; for 3.5h; | 96% |
With water; potassium bromide In chloroform at 25℃; pH=9; Electrochemical reaction; | 91% |
With chromium(VI) oxide; acetic acid | |
With air | |
With perchloric acid; water In acetonitrile at 20℃; Electrochemical reaction; Inert atmosphere; |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; H5PV2Mo10O40(1,11) In toluene for 24h; Ambient temperature; | A 96% B 4% |
With dinitrogen monoxide; Ru(5,10,15,20-tetramesitylporphyrin)(O)2 In benzene at 200℃; under 7600 Torr; for 20h; Product distribution; Further Variations:; Solvents; Reagents; Temperatures; | A 9% B 90% |
With dinitrogen monoxide; dioxo(tetramesitylporphyrinato)ruthenium(VI) In benzene at 200℃; under 7600 Torr; for 20h; Product distribution; Further Variations:; Reagents; Solvents; Temperatures; | A 9% B 90% |
Conditions | Yield |
---|---|
With water; potassium bromide In chloroform at 25℃; pH=9; Electrochemical reaction; | 96% |
Conditions | Yield |
---|---|
With methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate; oxygen; sodium acetate; nickel dibromide at 120℃; under 760.051 - 912.061 Torr; for 48h; chemoselective reaction; | A 94% B 96% |
1-<<(4-fluorophenyl)sulfonyl>oxy>-9,10-anthraquinone
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
With triethylammonium formate; palladium diacetate; 1,3-bis-(diphenylphosphino)propane In 1,4-dioxane at 90℃; for 0.5h; Product distribution; | 95% |
Conditions | Yield |
---|---|
With sodium bromate; nitric acid; Nafion-Ce(IV) In acetonitrile for 1h; Heating; | 95% |
With sodium bromate; Nafion-Ce(IV); Nafion-H In water; acetonitrile for 4h; Heating; | 90% |
With water; potassium bromide In chloroform at 25℃; pH=9; Electrochemical reaction; | 84% |
With air In water-d2 |
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
Stage #1: anthracene; phenanthrene; mixture of With manganese(II)carbonate; oxygen; acetic anhydride; acetic acid; sodium bromide at 100℃; for 24h; Stage #2: With water; dihydrogen peroxide at 50℃; for 2h; | 95% |
9,10-Diaminoanthrazene
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
With sodium periodate In water; ethyl acetate at 20℃; for 0.166667h; | 95% |
With [bis(acetoxy)iodo]benzene In acetone at 20℃; for 0.25h; | 90% |
Conditions | Yield |
---|---|
palladium on activated charcoal In toluene for 12h; Heating; | 94% |
With air |
9-methoxyanthracene-10-carboxaldehyde
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
With water; potassium bromide In chloroform at 25℃; pH=9; Electrochemical reaction; | 94% |
With N-Bromosuccinimide In water; N,N-dimethyl-formamide at 20 - 80℃; for 3h; | 92% |
bei der Oxydation; | |
With (bipyH2)-CrOCl5 In dichloromethane for 12h; Ambient temperature; other reagents, variation of conditions protic or aprotic media; |
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
With sodium hydroxide In water; acetonitrile at 20℃; for 5h; | 94% |
9,10-dihydroanthracen-9,10-dicarbaldehyde
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
With tetrafluoroboric acid diethyl ether; iodosylbenzene In diethyl ether; dichloromethane at 20℃; for 2h; | 93% |
9,10-bis(trimethylsilyloxy)anthracene
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
With lithium perchlorate In acetonitrile anode potential 1.0 V vs. SCE, graphite felt anode, 2.5 F mol-1; | 92% |
Conditions | Yield |
---|---|
at 24.84℃; Kinetics; Quantum yield; UV-irradiation; | 100% |
With aluminium(III) iodide In acetonitrile for 1h; Heating; | 70% |
With sodiumsulfide nonahydrate In ethanol at 78℃; for 2h; Inert atmosphere; | 10% |
Conditions | Yield |
---|---|
With sodium azide; sulfuric acid In dichloromethane at 0 - 20℃; | 100% |
With sodium azide; sulfuric acid In chloroform at 20 - 40℃; for 4h; | 97% |
Stage #1: 9,10-phenanthrenequinone With sulfuric acid In dichloromethane at 0℃; Schlenk technique; Inert atmosphere; Stage #2: With sodium azide In dichloromethane at 0 - 20℃; for 16h; Schlenk technique; Inert atmosphere; | 96% |
9,10-phenanthrenequinone
dimethyl 4,5-bis(methylthio)-1,3-dithiole phosphonate ester
bis[4,5-di(methylsulfanyl)-1,3-dithiol-2-ylidene]-9,10-dihydroanthracene
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667h; | 100% |
With n-butyllithium In tetrahydrofuran; hexane 1.) -78 deg C, 0.5 h, 2.) -78 deg C, 1 h; -78 deg C to r.t., overnight; | 38% |
9,10-phenanthrenequinone
10-[1-(prop-2-enyl)]-10-hydroxy-9(10H)-anthracenone
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at -23℃; for 3h; | 100% |
N-benzylglycine
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
With formaldehyd In 1,4-dioxane; benzene for 3h; Reflux; Dean-Stark; | 100% |
Conditions | Yield |
---|---|
In 1,4-dioxane; benzene for 3h; Dean-Stark; Reflux; | 100% |
Conditions | Yield |
---|---|
With oxygen; nickel In xylene in a cyclic oxidation process, anthraquinone in xylol/2-octanol (1:1) is reduced over Ni/H2, the cat. is removed and sodium metaborate (containing seed crystals of peroxoborate) is added; subsequent oxidation with O2 at 30°C for 20-30 min.;; containing 10% of active oxygene;; | 99.5% |
With O2; nickel In xylene; further solvent(s) in a cyclic oxidation process, anthraquinone in xylol/2-octanol (1:1) is reduced over Ni/H2, the cat. is removed and sodium metaborate (containing seed crystals of peroxoborate) is added; subsequent oxidation with O2 at 30°C for 20-30 min.;; containing 10% of active oxygene;; | 99.5% |
Conditions | Yield |
---|---|
In water; nitric acid | 99.2% |
With phosphoric acid; sulfuric acid; nitric acid In tetrachloromethane for 6h; Ambient temperature; | 90% |
With nitric acid In water | 71% |
9,10-phenanthrenequinone
formamide
9,10-bis(formamido)anthracene
Conditions | Yield |
---|---|
for 12h; Reflux; | 99% |
Conditions | Yield |
---|---|
With hydrogen iodide; acetic acid for 120h; Heating; | 99% |
With phenylphosphane at 140℃; for 72h; | 91% |
With potassium hydroxide; Raney Ni-Al alloy In water at 90℃; for 8h; | 91% |
Conditions | Yield |
---|---|
With triphenylphosphine In benzene at 20℃; for 24h; Corey-Fuchs olefination; | 99% |
With triphenylphosphine In benzene at 20℃; for 24h; | 96% |
With triphenylphosphine In dichloromethane at 20℃; | 91% |
Conditions | Yield |
---|---|
Stage #1: 9,10-phenanthrenequinone With sulfuric acid; hydrogen; sodium dodecyl-sulfate In chlorobenzene under 10501.1 Torr; Heating; Stage #2: glycerol With sulfuric acid In chlorobenzene Reagent/catalyst; Pressure; Heating; | 98.8% |
in schwefelsaurer Loesung; | |
With sulfuric acid; acetic anhydride |
Conditions | Yield |
---|---|
In nitric acid-treated palladium; sulfuric acid | 98% |
With sulfuric acid; sulfur trioxide; mercury at 130℃; | |
With mercurosulfate; sulfuric acid; sulfur trioxide at 150℃; |
9,10-phenanthrenequinone
cis-11,12-Dicyano-9,10-ethano-9,10-dihydro-9,10-dihydroxyanthracene
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In pyridine for 2h; | 98% |
9,10-phenanthrenequinone
dimethyl 1,3-benzodithiol-2-ylphosphonate
9,10-bis-(1,3-benzdithiol-2-ylidene)-9,10-dihydroanthracene
Conditions | Yield |
---|---|
Stage #1: dimethyl 1,3-benzodithiol-2-ylphosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Wittig-Horner reaction; Stage #2: 9,10-phenanthrenequinone In tetrahydrofuran; hexane at 20℃; | 98% |
With n-butyllithium 1.) THF, -78 deg C, 20 min, 2.) -78 deg C, 1 h -> r.t., 24 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With aluminum (III) chloride; triethylamine In chloroform at 20℃; for 2h; | 97.2% |
With boric acid; tin(ll) chloride | |
With aluminium trichloride | |
With aluminum tri-bromide |
9,10-phenanthrenequinone
phenyltellurotrimethylsilane
9,10-bis(trimethylsilyloxy)anthracene
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 0.5h; reductive silylation; | 97% |
Molecular Structure of Anthraquinone (CAS NO.84-65-1):
Molecular Formula: C14H8O2
Molecular Weight: 208.2121
IUPAC Name: Anthracene-9,10-dione
Synonyms of Anthraquinone (CAS NO.84-65-1): Anthraquinone [BSI:ISO] ; 9,10-Anthracenedione ; 9,10-Anthrachinon ; 9,10-Anthrachinon [Czech] ; 9,10-Anthraquinone ; 9,10-Dioxoanthracene ; AI3-09073 ; Anthracene, 9,10-dihydro-9,10-dioxo- ; Bis-alkylamino anthraquinone ; CCRIS 649 ; Caswell No. 052A ; Corbit ; EINECS 201-549-0 ; EPA Pesticide Chemical Code 122701 ; HSDB 2074 ; Hoelite ; Morkit ; NSC 7957
CAS NO: 84-65-1
Classification Code: Agricultural Chemical ; Avicide ; Mutation data ; TSCA Flag T [Subject to the Section 4 test rule under TSCA] ; Tumor data
Melting Point: 284-286 °C
Index of Refraction: 1.659
Molar Refractivity: 58.66 cm3
Molar Volume: 159 cm3
Surface Tension: 55.8 dyne/cm
Density: 1.308 g/cm3
Flash Point: 141.4 °C
Enthalpy of Vaporization: 62.47 kJ/mol
Boiling Point: 377 °C at 760 mmHg
Vapour Pressure: 6.97E-06 mmHg at 25°C
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | oral | > 5gm/kg (5000mg/kg) | Pesticide Manual. Vol. 9, Pg. 37, 1991. | |
quail | LD50 | unreported | > 2gm/kg (2000mg/kg) | Farm Chemicals Handbook. Vol. -, Pg. C23, 1991. | |
rat | LC50 | inhalation | > 1300mg/m3/4H (1300mg/m3) | Pesticide Manual. Vol. 9, Pg. 37, 1991. | |
rat | LD50 | intraperitoneal | 3500mg/kg (3500mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 21(12), Pg. 27, 1977. | |
rat | LD50 | skin | > 1gm/kg (1000mg/kg) | "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A019, Pg. 1983, | |
rat | LDLo | oral | 15gm/kg (15000mg/kg) | "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 22, 1982. |
Anthraquinone (CAS NO.84-65-1) is reported in EPA TSCA Inventory.
Hazard Codes of Anthraquinone (CAS NO.84-65-1): Xi
Risk Statements: 43-36/37/38
R43: May cause sensitization by skin contact.
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 36/37-39-26-24
S36/37: Wear suitable protective clothing and gloves.
S39: Wear eye / face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S24: Avoid contact with skin.
WGK Germany: 1
RTECS: CB4725000
1. Fire Fighting Measures
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.
2. Handling and Storage
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation.
Storage: Store in a cool, dry place. Store in a tightly closed container.
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