Conditions | Yield |
---|---|
With pyrophosphoryl chloride at 20℃; for 0.5h; | 100% |
With 2C2H3F3O*BF3 In dichloromethane Friedel-Crafts acylation; | 100% |
With Nafion-H In various solvent(s) at 180℃; for 2h; Acylation; Friedel-Crafts intramolecular acylation; | 92% |
9,10-bis(trimethylsilyl)-9,10-dihydro-9,10-epoxyanthracene
anthracen-9(10H)-one
Conditions | Yield |
---|---|
With trifluoroacetic acid In chloroform-d1 for 0.0833333h; | 100% |
anthracen-9(10H)-one oxime
anthracen-9(10H)-one
Conditions | Yield |
---|---|
With dihydrogen peroxide; tripropylammonium fluorochromate (VI) In acetone at 0 - 10℃; for 6.5h; | 97% |
With CuCl*Kieselghur; oxygen In dichloromethane at 20℃; for 0.5h; | 85% |
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% |
Conditions | Yield |
---|---|
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; cobalt(II) diacetate tetrahydrate In dichloromethane; water at 0 - 5℃; for 6h; pH=8.3; | 96% |
With manganese(IV) oxide at 105℃; for 0.0416667 - 0.0666667h; Inert atmosphere; Microwave irradiation; | 90% |
With tert.-butylhydroperoxide; 0.5C34H18N16(4-)*2H2O*2Cu(1+)*C3H7NO In water at 20℃; for 4h; Reagent/catalyst; Sonication; | 87% |
Conditions | Yield |
---|---|
With dihydrogen peroxide In water; acetonitrile at 25℃; for 1.58333h; | 96% |
With tert.-butylnitrite; oxygen; 3,6-di(2'-pyridyl)-1,2,4,5-tetrazine; acetic acid In acetonitrile at 20℃; for 4.5h; Irradiation; | 87% |
With ammonium nitrate; hydrogenchloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In water; acetonitrile at 60℃; for 6h; Green chemistry; | 82% |
Conditions | Yield |
---|---|
With porcine liver esterase In aq. phosphate buffer; dimethyl sulfoxide at 37℃; for 1h; pH=7.5; Reagent/catalyst; Enzymatic reaction; | 94% |
9,10-dihydroanthracen-9-ol
A
anthracene
B
anthracen-9(10H)-one
C
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
With aluminum oxide; Ru(OH)x; oxygen In para-xylene at 129.85℃; under 760 Torr; for 0.166667h; | A 91% B 7% C 2% |
Conditions | Yield |
---|---|
With potassium hydride In tetrahydrofuran at 25℃; for 0.5h; | A n/a B 90% |
Anthronesemicarbazone
anthracen-9(10H)-one
Conditions | Yield |
---|---|
With potassium permanganate; silica gel In water at 20℃; for 0.25h; | 88% |
With barium permanganate In acetonitrile for 4h; Heating; | 51% |
9,10-dihydroanthracene
A
anthracene
B
anthracen-9(10H)-one
C
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
With aluminum oxide; Ru(OH)x; oxygen In para-xylene at 129.85℃; under 760 Torr; for 4h; Product distribution; Further Variations:; Reagents; | A 88% B n/a C n/a |
With oxygen In acetonitrile at 25℃; for 24h; Sealed tube; Irradiation; Green chemistry; | A 20% B 9% C 71% |
With [Mn(IV)(O)(BQCN)(H2O)](2+) In water; acetonitrile at 0℃; Kinetics; Concentration; Inert atmosphere; | A 22% B 11% C 14% |
Conditions | Yield |
---|---|
In sulfuric acid at 25℃; Rate constant; electrochemical reduction at glassy carbon electrode; | 87% |
electrolysis at a rotating glassy carbon cylinder electrode (U=-0.7 V); | 87% |
With sodium hydroxide; sodium dithionite at 150 - 160℃; |
Anthrone 2,4-dinitrophenylhydrazone
anthracen-9(10H)-one
Conditions | Yield |
---|---|
With barium permanganate In acetonitrile for 2h; Heating; | 85% |
anthracen-9(10H)-one
Conditions | Yield |
---|---|
With oxygen; kieselguhr; copper(l) chloride In toluene for 4h; Oxidation; Heating; | 81% |
9,10-phenanthrenequinone
A
2-hydroxy-9,10-anthraquinone
B
anthracen-9(10H)-one
C
1-hydroxyanthraquinone
D
bianthronyl
Conditions | Yield |
---|---|
In sulfuric acid at 15℃; Product distribution; Mechanism; Quantum yield; Irradiation; N2; | A 80% B n/a C n/a D n/a |
In sulfuric acid at 15℃; Irradiation; | A 80% B n/a C n/a D n/a |
9,10-dihydroanthracen-9-ol
A
anthracen-9(10H)-one
B
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
With manganese(III) Schiff-base; dihydrogen peroxide at 20℃; for 4.5h; | A 80% B 16% |
2-(benzyl)benzoyl chloride
anthracen-9(10H)-one
Conditions | Yield |
---|---|
With 1,1,1,3',3',3'-hexafluoro-propanol at 20℃; for 5h; Friedel-Crafts Acylation; Inert atmosphere; | 77% |
In 1,2-dichloro-ethane at 23℃; for 2h; Friedel-Crafts Acylation; Inert atmosphere; | 77% |
Nafion-H In benzene for 0.25h; Heating; | 71 % Chromat. |
Conditions | Yield |
---|---|
With potassium carbonate In chloroform at 20℃; for 24h; Irradiation; Inert atmosphere; | 75% |
1,4,4a,9a-tetrahydroanthraquinone
A
anthracen-9(10H)-one
B
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; sodium sulfite at 180℃; for 1h; | A 70% B 10% |
10-diazo-10H-anthracen-9-one
butyl magnesium bromide
A
anthracen-9(10H)-one
B
10-butyl-10-hydroxy-anthrone
C
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
In benzene for 2h; Ambient temperature; Further byproducts given; | A 2% B 3% C 20% D 62% |
2-Methylbenzophenone
p-benzoquinone
A
anthracen-9(10H)-one
B
2-[2-(2-benzoylphenyl)ethyl]benzophenone
Conditions | Yield |
---|---|
In benzene Product distribution; Irradiation; laser jet; | A 19% B 6% C 60% |
In benzene Irradiation; | A 19% B 6% C 60% |
2-benzylidene-1-phenylbenzocyclobuten-1-ol
A
anthracen-9(10H)-one
B
9-benzylanthracene
C
benzylideneanthrone
D
10-benzyl-9(10H)-anthracenone
E
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
In decalin for 16h; Product distribution; Heating; other 2-benzylidene-benzocyclobuten-1-ols; | A n/a B n/a C 50% D 24% E 15% |
9,10-dihydroanthracene
acetic acid
A
anthracen-9(10H)-one
B
acetic acid 10-oxo-9,10-dihydro-anthracen-9-yl ester
C
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
With sodium acetate In acetonitrile anodic oxidadion; | A 7% B 48% C 15% |
Conditions | Yield |
---|---|
With [Mn(IV)(O)(BQCN)(H2O)](2+) In water; acetonitrile at 0℃; Kinetics; Concentration; Inert atmosphere; | A 47% B 17% |
With sodium hydroxide at 80 - 85℃; Einleiten von Chlor; | |
With copper diacetate; oxygen; sodium chloride In acetic acid at 90℃; under 380 Torr; for 1h; Rate constant; Product distribution; Mechanism; var. conc. of Cu(OAc)2 and NaCl, different times; | |
for 2h; Photolysis; |
anthracene
A
anthracen-9(10H)-one
B
oxanthrone
C
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
With phosphate buffer; Fe(III) meso-tetrakis(3,5-disulfonatomesityl)porphyrin; dihydrogen peroxide In acetonitrile at 20℃; for 0.5h; Mechanism; | A n/a B 5% C 21% |
With phosphate buffer; Fe(III) tetrasulfophthalocyanine; dihydrogen peroxide In acetonitrile at 20℃; for 0.0166667h; | A n/a B 5 % Chromat. C 21 % Chromat. |
With potassium peroxomonosulfate; phosphate buffer; Fe(III) meso-tetrakis(3,5-disulfonatomesityl)porphyrin In acetonitrile at 20℃; for 1h; | A n/a B 43 % Chromat. C 16 % Chromat. |
Conditions | Yield |
---|---|
With oxygen In acetone for 10h; Irradiation; | A 6.8% B 20.7% |
methanol
10-(Diethoxymethyl)-9-anthrone
A
anthracen-9(10H)-one
B
10-(Dimethoxymethyl)-9-anthrone
Conditions | Yield |
---|---|
With sodium methylate for 0.333333h; | A 3% B 5% |
Conditions | Yield |
---|---|
With aluminium trichloride; benzene |
diethyl ether
10-bromo-10H-anthracen-9-one
A
anthracen-9(10H)-one
B
bianthronyl
C
9,10-phenanthrenequinone
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% |
Conditions | Yield |
---|---|
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane for 1.5h; Ambient temperature; | 100% |
With sodium hydroxide In water for 2h; | 70% |
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane; water for 1h; Schlenk technique; Inert atmosphere; | 63% |
With lithium methanolate |
N-methylmaleimide
anthracen-9(10H)-one
4-Hydroxy-2-methyl-3a,4,9,9a-tetrahydro-4,9<1',2'>benzeno-1H-benzisoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 0.25h; Ambient temperature; other anthrones, other dienophiles; | 100% |
In N,N-dimethyl-formamide at 25℃; Product distribution; other related phenols, hydroquinones, and naphthacene analogues, other dienophiles, var. solvents and temperatures; solvent-dependent diene reactivity, base-catalyzed Diels-Alder reaction; | 100% |
With triethylamine In tetrahydrofuran at 24℃; for 0.25h; | 100% |
dihydroquinidine 9-O-(4-chlorobenzoate) In chloroform |
(E/Z)-crotyl bromide
anthracen-9(10H)-one
10,10-Dibut-2-enylanthrone
Conditions | Yield |
---|---|
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane for 1.5h; Ambient temperature; | 100% |
anthracen-9(10H)-one
cis-11,12-Dicyano-9,10-dihydro-9-hydroxy-9,10-ethanoanthracene
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 1h; | 100% |
anthracen-9(10H)-one
trans-1-(4-fluorophenyl)-2-nitro-ethene
Conditions | Yield |
---|---|
With O-benzoylcupreine In dichloromethane at -40℃; for 12h; asymmetric Michael addition reaction; | 99% |
anthracen-9(10H)-one
Conditions | Yield |
---|---|
With C15H22FN3S In dichloromethane at -20℃; for 24h; Michael condensation; optical yield given as %ee; enantioselective reaction; | 99% |
anthracen-9(10H)-one
(E)-5-(2-bromostyryl)-3-methyl-4-nitro-isoxazole
Conditions | Yield |
---|---|
With C15H22FN3S In dichloromethane at -20℃; for 24h; Michael condensation; optical yield given as %ee; enantioselective reaction; | 99% |
anthracen-9(10H)-one
(E)-5-(3-bromostyryl)-3-methyl-4-nitroisoxazole
Conditions | Yield |
---|---|
With C15H22FN3S In dichloromethane at -20℃; for 24h; Michael condensation; optical yield given as %ee; enantioselective reaction; | 99% |
(E)-3-methyl-4-nitro-5-styrylisoxazole
anthracen-9(10H)-one
Conditions | Yield |
---|---|
With C15H22FN3S In dichloromethane at -20℃; for 24h; Michael condensation; optical yield given as %ee; enantioselective reaction; | 99% |
anthracen-9(10H)-one
Conditions | Yield |
---|---|
Stage #1: anthracen-9(10H)-one With sodium hydride In tetrahydrofuran at -20℃; for 0.166667h; Inert atmosphere; Darkness; Stage #2: 2-chlorocarbonyl-1,4-dimethylnaphthalene In tetrahydrofuran at -20℃; for 1.08333h; Inert atmosphere; Darkness; | 99% |
anthracen-9(10H)-one
4-acetoxybenzyl chloride
10,10-bis-(4-hydroxybenzyl)-9(10H)-anthracenone
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane; water at 95℃; for 2h; | 98% |
anthracen-9(10H)-one
9,10-anthraquinone-9-oxime
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite In N,N-dimethyl-formamide for 12h; ice bath; | 98% |
With hydrogenchloride; sodium nitrite In N,N-dimethyl-formamide at 25℃; for 12h; | 80% |
Stage #1: anthracen-9(10H)-one With sodium; isopentyl nitrite In ethanol at 20℃; Inert atmosphere; Stage #2: With hydrogenchloride In ethanol; water Cooling with ice; Inert atmosphere; | 57% |
anthracen-9(10H)-one
1-nitro-2-(4-chlorophenyl)ethylene
Conditions | Yield |
---|---|
With O-benzoylcupreine In dichloromethane at -40℃; for 12h; asymmetric Michael addition reaction; | 98% |
Conditions | Yield |
---|---|
With C50H38N10O6 In toluene at 20℃; for 48h; Catalytic behavior; Reagent/catalyst; Time; Solvent; Michael Addition; enantioselective reaction; | 98% |
With O-benzoylcupreine In dichloromethane at -40℃; for 12h; asymmetric Michael addition reaction; | 94% |
Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium chloride at 20℃; for 0.5h; Diels-Alder reaction; | 98% |
With triethylamine In dichloromethane at 23℃; for 3h; Diels-Alder reaction; | |
With triethylamine In chloroform at 20℃; for 24h; |
anthracen-9(10H)-one
4-(3-Bromphenyl)-3-buten-2-on
(S)-9-(1-(3-bromophenyl)-3-oxobutyl)anthracen-10(9H)-one
Conditions | Yield |
---|---|
With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methyl)thiourea In toluene at 20℃; for 72h; Michael addition; optical yield given as %ee; enantioselective reaction; | 98% |
anthracen-9(10H)-one
2-chlorobenzalacetone
(S)-9-(1-(2-chlorophenyl)-3-oxobutyl)anthracen-10(9H)-one
Conditions | Yield |
---|---|
With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methyl)thiourea In toluene at 20℃; for 72h; Michael addition; optical yield given as %ee; enantioselective reaction; | 98% |
Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium chloride at 20℃; for 0.5h; Diels-Alder reaction; | 98% |
Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium chloride at 20℃; for 0.5h; Diels-Alder reaction; | 98% |
Anthrone (CAS NO.90-44-8) is reported in EPA TSCA Inventory.
1.Introduction of Anthrone
The Anthrone, with its CAS NO 90-44-8, is a kind of off-white to light yellow crystals. It has synonyms of Anthrone(6CI,8CI);9-Oxoanthracene;Anthracene, 9,10-dihydro-9-oxo-;Carbothrone and NSC1965. Anthrone should be stored in a cool, dry place and in a tightly closed container. It is mainly used for a popular cellulose assay and in the colorometric determination of carbohydrates.
2.Properties of Anthrone
(1) Molecular Weight: 194.2286 (2) IUPAC Name: 10H-anthracen-9-one (3) Appearance: off-white to light yellow crystals
(4) Nominal Mass: 194 Da (5) Average Mass: 194.2286 Da (6) Monoisotopic Mass: 194.073165 Da
(7) Index of Refraction: 1.639 (8) Molar Refractivity: 58.53 cm3 (9) Molar Volume: 162.5 cm3
(10) Surface Tension: 48.7 dyne/cm (11) Density: 1.194 g/cm3 (12) Flash Point: 150.3 °C
(13) Enthalpy of Vaporization: 58.72 kJ/mol (14) Boiling Point: 343.4 °C at 760 mmHg (15) Vapour Pressure: 7.07E-05 mmHg at 25°C
3.Structure descriptors of Anthrone
IUPAC Name: 10H-anthracen-9-one
InChI: InChI=1S/C14H10O/c15-14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-8H,9H2
InChIKey: RJGDLRCDCYRQOQ-UHFFFAOYSA-NCanonical SMILES : C1C2=CC=CC=C2C(=O)C3=CC=CC=C31
4.Safety information of Anthrone
Hazard Codes: XnXi
Risk Statements: 36/37/38-20/21/22
R36/37/38: Irritating to eyes, respiratory system and skin
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36: Wear suitable protective clothing
WGK Germany: 3
RTECS: CB8925500
F: 8
Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
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