9,9-Dimethyl-10-(trimethylsilyl)-9,10-dihydroanthracene
10,10-dimethyl-9,10-dihydroanthracen-9-one
Conditions | Yield |
---|---|
With sodium dichromate; acetic acid for 12h; Ambient temperature; | 90% |
With sodium dichromate; acetic acid for 12h; Ambient temperature; other 9,9-dialkyl-10-(trimethylsilyl)- and 9,9-dialkyl-9,10-dihydroanthracenes; | 90% |
9-diazo-10,10-dimethyl-9,10-dihydroanthracene
A
10,10-dimethyl-9,10-dihydroanthracen-9-one
B
10-[10,10-dimethyl-9(10H)-anthracenyl]-9,10-dihydro-9,9-dimethylanthracene
Conditions | Yield |
---|---|
With (Z)-2-Butene Irradiation; | A 8% B 80% |
9,10-Dihydro-10,10-dimethylanthracen
10,10-dimethyl-9,10-dihydroanthracen-9-one
Conditions | Yield |
---|---|
With bromine In tetrachloromethane for 6h; Heating; Irradiation; | 70% |
With chromium(VI) oxide In acetic acid |
(8aR,9R)-8a,9-Dimethyl-8a,9-dihydro-anthracen-9-ol
A
10,10-dimethyl-9,10-dihydroanthracen-9-one
B
9,10-Dihydro-10,10-dimethylanthracen
Conditions | Yield |
---|---|
With sulfuric acid; acetic anhydride In acetic acid | A 25% B 53% |
9,9a-dihydro-9,9a-dimethyl-9-anthracenol
A
10,10-dimethyl-9,10-dihydroanthracen-9-one
B
9,10-Dihydro-10,10-dimethylanthracen
Conditions | Yield |
---|---|
With sulfuric acid; acetic anhydride In acetic acid at 23℃; for 2.25h; | A 25% B 53% |
acetic anhydride
9,9a-dihydro-9,9a-dimethyl-9-anthracenol
A
10,10-dimethyl-9,10-dihydroanthracen-9-one
B
9,10-Dihydro-10,10-dimethylanthracen
C
10,10-dimethyl-9,10-dihydroanthranylacetic acid
Conditions | Yield |
---|---|
With sulfuric acid for 2h; Yields of byproduct given; | A n/a B n/a C 45% |
dimethylketene
N-(10,10-dimethyl-9,10-dihydroanthracen-9-ylidene)phenylamine N-oxide
A
10,10-dimethyl-9,10-dihydroanthracen-9-one
B
4',4',10,10-tetramethyl-3'-phenyl-9,10-dihydroanthracene-9-spiro-2'-oxazolidin-5'-one
Conditions | Yield |
---|---|
In ethyl acetate Ambient temperature; | A 150 mg B 24% |
2-(1-hydroxy-1-methyl-ethyl)-benzophenone cyclohemiacetal
10,10-dimethyl-9,10-dihydroanthracen-9-one
Conditions | Yield |
---|---|
With sulfuric acid at 150℃; for 1.5h; | 20% |
With PPA | |
With sulfuric acid at 150 - 155℃; for 5h; | 105 g |
(8aR,9R)-8a,9-Dimethyl-8a,9-dihydro-anthracen-9-ol
A
10,10-dimethyl-9,10-dihydroanthracen-9-one
B
9,10-Dihydro-10,10-dimethylanthracen
C
10,10-dimethyl-9,10-dihydroanthranylacetic acid
Conditions | Yield |
---|---|
A 10% B 15% C 75 % Spectr. |
anthracen-9(10H)-one
methyl iodide
10,10-dimethyl-9,10-dihydroanthracen-9-one
Conditions | Yield |
---|---|
12% | |
With potassium hydroxide | |
(i) Li, MeOH, toluene, (ii) /BRN= 969135/, tBuOH; Multistep reaction; | |
With lithium methanolate 1) toluene, 100-120 deg C; 140 deg C 2) tBuOH, 24 h, 140-150 deg C; Yield given. Multistep reaction; | |
With sodium hydroxide In dichloromethane at 20℃; for 15h; | 100 % Spectr. |
Conditions | Yield |
---|---|
Lithium-Verbindung; | |
With water; potassium carbonate |
anthracen-9(10H)-one
methyl iodide
A
10,10-dimethyl-9,10-dihydroanthracen-9-one
B
methyl-9-methoxy-10-anthracene
Conditions | Yield |
---|---|
With potassium hydroxide |
o-Isopropylbenzophenon-oxim
chloroacetic acid
10,10-dimethyl-9,10-dihydroanthracen-9-one
Conditions | Yield |
---|---|
(i) NaOH, aq. EtOH, (ii) K2S2O8, aq. NaOH; Multistep reaction; |
9,10-dihydro-10,10-dimethyl-9-anthracenol
A
10,10-dimethyl-9,10-dihydroanthracen-9-one
B
9,10-Dihydro-10,10-dimethylanthracen
Conditions | Yield |
---|---|
With sulfuric acid In acetic acid for 3h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
methylene chloride
10-nitro-9-methylanthracene
10,10-dimethyl-9,10-dihydroanthracen-9-one
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
9,10-dihydro-10,10-dimethyl-9-anthracenol
acetic anhydride
A
10,10-dimethyl-9,10-dihydroanthracen-9-one
B
9,10-Dihydro-10,10-dimethylanthracen
C
10,10-dimethyl-9,10-dihydroanthranylacetic acid
Conditions | Yield |
---|---|
With sulfuric acid for 2h; Yields of byproduct given; |
anthracen-9(10H)-one
methyl iodide
A
10,10-dimethyl-9,10-dihydroanthracen-9-one
B
methyl-9-methoxy-10-anthracene
C
9-methoxyanthracene
D
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
With potassium hydroxide; 18-crown-6 ether 1.) toluene, 70 deg C, 2.) toluene, 70 deg C, 3.5 h; r.t. 12 h; Yield given. Multistep reaction. Yields of byproduct given; | |
With potassium hydroxide; 18-crown-6 ether 1.) toluene, 70 deg C, 2.) toluene, 70 deg C, 3.5 h; r.t. 12 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With toluene Erhitzen des Reaktionsprodukts mit CH3I und wenig tert-Butylalkohol; |
anthracen-9(10H)-one
methyl iodide
10,10-dimethyl-9,10-dihydroanthracen-9-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 83 percent / diethyl ether / 0 °C 2: 20 percent / H2SO4 / 1.5 h / 150 °C View Scheme | |
Multi-step reaction with 2 steps 2: polyphosphoric acid View Scheme | |
Multi-step reaction with 2 steps 1.1: magnesium; iodine / tetrahydrofuran / 2 h / Reflux 1.2: 5 h / 20 °C 2.1: sulfuric acid / 5 h / 150 - 155 °C View Scheme |
9a-hydro-9a-methyl-9-anthracenone
10,10-dimethyl-9,10-dihydroanthracen-9-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 71 percent / diethyl ether / 1.) -70 deg C -> 0 deg C, 1 h, 2.) 23 deg C, 1 h 2: 25 percent / conc. sulfuric acid, acetic anhydride / acetic acid / 2.25 h / 23 °C View Scheme | |
Multi-step reaction with 2 steps 1: 71 percent 2: 25 percent / sulfuric acid, Ac2O / acetic acid View Scheme | |
Multi-step reaction with 2 steps 1: 71 percent 2: 10 percent View Scheme |
C23H22N2O2S
10,10-dimethyl-9,10-dihydroanthracen-9-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 77 percent / sodium methoxide / pyridine / 70 °C 2: 8 percent / cis-2-butene / Irradiation View Scheme |
1,4,9a-trihydro-9a-methyl-9-anthracenone
10,10-dimethyl-9,10-dihydroanthracen-9-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.)Bromine 2.)DBU / 2.)benzene 2: 71 percent 3: 25 percent / sulfuric acid, Ac2O / acetic acid View Scheme | |
Multi-step reaction with 3 steps 1: 1.)Bromine 2.)DBU / 2.)benzene 2: 71 percent 3: 10 percent View Scheme | |
Multi-step reaction with 4 steps 1: 55 percent / methylenetriphenylphosphorane 2: 1.)Bromine 2.)DBU / 2.)benzene 3: 71 percent 4: 25 percent / sulfuric acid, Ac2O / acetic acid View Scheme | |
Multi-step reaction with 4 steps 1: 55 percent / methylenetriphenylphosphorane 2: 1.)Bromine 2.)DBU / 2.)benzene 3: 71 percent 4: 10 percent View Scheme |
1,2,9a-trihydro-9a-methyl-9-anthracenone
10,10-dimethyl-9,10-dihydroanthracen-9-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.)Bromine 2.)DBU / 2.)benzene 2: 71 percent 3: 25 percent / sulfuric acid, Ac2O / acetic acid View Scheme | |
Multi-step reaction with 3 steps 1: 1.)Bromine 2.)DBU / 2.)benzene 2: 71 percent 3: 10 percent View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: magnesium / tetrahydrofuran / 2 h / Reflux 1.2: 2 h / 20 °C 2.1: magnesium; iodine / tetrahydrofuran / 2 h / Reflux 2.2: 5 h / 20 °C 3.1: sulfuric acid / 5 h / 150 - 155 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: magnesium; iodine / tetrahydrofuran / 2 h / Reflux 1.2: 2 h / 20 °C 2.1: magnesium; iodine / tetrahydrofuran / 2 h / Reflux 2.2: 5 h / 20 °C 3.1: sulfuric acid / 5 h / 150 - 155 °C View Scheme |
Conditions | Yield |
---|---|
Stage #1: 3-(Dimethylamino)propyl chloride With iodine; magnesium In diethyl ether; ethylene dibromide at 30 - 35℃; for 9h; Reflux; Large scale; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In diethyl ether; ethylene dibromide at 10 - 35℃; for 1h; Reflux; Large scale; | 97.2% |
10,10-dimethyl-9,10-dihydroanthracen-9-one
10,10-dimethylanthrone hydrazone
Conditions | Yield |
---|---|
With hydrazine hydrochloride; hydrazine hydrate In various solvent(s) Heating; | 95% |
With hydrazinium sulfate; hydrazine Heating; Yield given; |
Conditions | Yield |
---|---|
Stage #1: 9,10-Dibromoanthracene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran; hexane at 20℃; for 16h; Inert atmosphere; | 93% |
10,10-dimethyl-9,10-dihydroanthracen-9-one
(4-bromophenyl)magnesium bromide
Conditions | Yield |
---|---|
In tetrahydrofuran at 60℃; for 24h; Grignard Reaction; | 88% |
Conditions | Yield |
---|---|
Stage #1: 1.4-dibromobenzene With magnesium In tetrahydrofuran for 4h; Inert atmosphere; Reflux; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran at 60℃; for 24h; | 88% |
10,10-dimethyl-9,10-dihydroanthracen-9-one
9,10-Dihydro-10,10-dimethylanthracen
Conditions | Yield |
---|---|
With dimethylsulfide borane complex In tetrahydrofuran for 2h; Reflux; | 85% |
With lithium aluminium tetrahydride; aluminium trichloride In diethyl ether for 0.333333h; Heating; | 27% |
With potassium hydroxide; hydrazine hydrate In ethylene glycol | |
With hydrazine In diethylene glycol for 4h; Heating; |
4-(4-bromophenyl)dibenzofuran
10,10-dimethyl-9,10-dihydroanthracen-9-one
Conditions | Yield |
---|---|
Stage #1: 4-(4-bromophenyl)dibenzofuran With magnesium In tetrahydrofuran for 4h; Inert atmosphere; Reflux; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; | 85% |
10,10-dimethyl-9,10-dihydroanthracen-9-one
Conditions | Yield |
---|---|
Stage #1: 4-(2-bromo-4-chlorophenyl)dibenzofuran With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran at -78 - 20℃; for 1h; | 85% |
10,10-dimethyl-9,10-dihydroanthracen-9-one
(4-(di([1,1’-biphenyl]-4-yl)amino)phenyl)boronic acid
Conditions | Yield |
---|---|
Stage #1: 10,10-dimethyl-9,10-dihydroanthracen-9-one With toluene-4-sulfonic acid hydrazide In toluene at 80℃; for 2h; Stage #2: (4-(di([1,1’-biphenyl]-4-yl)amino)phenyl)boronic acid With potassium carbonate In toluene at 110℃; for 5h; | 84% |
Conditions | Yield |
---|---|
Stage #1: 10,10-dimethyl-9,10-dihydroanthracen-9-one With toluene-4-sulfonic acid hydrazide In toluene at 80℃; for 2h; Stage #2: C44H39BN2O2 With potassium carbonate In toluene at 110℃; for 5h; | 84% |
Conditions | Yield |
---|---|
Stage #1: 10,10-dimethyl-9,10-dihydroanthracen-9-one With toluene-4-sulfonic acid hydrazide In toluene at 80℃; for 2h; Stage #2: C32H24BNO2 With potassium carbonate In toluene at 110℃; for 5h; | 83% |
10,10-dimethyl-9,10-dihydroanthracen-9-one
Conditions | Yield |
---|---|
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 18h; Darkness; | 83% |
10,10-dimethyl-9,10-dihydroanthracen-9-one
1-Bromo-5-chloronaphthalene
Conditions | Yield |
---|---|
Stage #1: 1-Bromo-5-chloronaphthalene With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran at 0℃; for 10h; Inert atmosphere; | 83% |
Conditions | Yield |
---|---|
Stage #1: 2-bromo-7-chloronaphthalene With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran at 20℃; for 10h; Inert atmosphere; | 83% |
Conditions | Yield |
---|---|
Stage #1: 2-(4-bromophenyl]pyridine With magnesium In tetrahydrofuran for 4h; Inert atmosphere; Reflux; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; | 82% |
bromobenzene
10,10-dimethyl-9,10-dihydroanthracen-9-one
10,10-dimethyl-9-phenyl-9,10-dihydroanthracen-9-ol
Conditions | Yield |
---|---|
Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 3.5h; Inert atmosphere; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran at -78 - 20℃; for 16h; | 82% |
Stage #1: bromobenzene With iodine; magnesium In tetrahydrofuran at 40 - 80℃; for 4h; Inert atmosphere; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran for 15h; Inert atmosphere; Reflux; | 76.8% |
Stage #1: bromobenzene With iodine; magnesium In tetrahydrofuran at 40 - 80℃; for 4h; Inert atmosphere; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran for 15h; Inert atmosphere; Reflux; | 76.3% |
10,10-dimethyl-9,10-dihydroanthracen-9-one
1-bromo-4-chloronaphthalene
Conditions | Yield |
---|---|
Stage #1: 1-bromo-4-chloronaphthalene With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran at 20℃; for 10h; Inert atmosphere; | 82% |
Conditions | Yield |
---|---|
Stage #1: 10,10-dimethyl-9,10-dihydroanthracen-9-one With toluene-4-sulfonic acid hydrazide In toluene at 80℃; for 2h; Stage #2: C27H25BN2O3 With potassium carbonate In toluene at 110℃; for 5h; | 81% |
Conditions | Yield |
---|---|
Stage #1: 10,10-dimethyl-9,10-dihydroanthracen-9-one With toluene-4-sulfonic acid hydrazide In toluene at 80℃; for 2h; Stage #2: C41H35BN2O2 With potassium carbonate In toluene at 110℃; for 5h; | 81% |
10,10-dimethyl-9,10-dihydroanthracen-9-one
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 5℃; for 0.5h; | 80% |
With sulfuric acid; nitric acid at 5 - 10℃; for 0.5h; | 80% |
With sulfuric acid; nitric acid at 5 - 10℃; for 0.5h; | 80% |
With nitric acid at 5 - 10℃; for 0.5h; | 80% |
With sulfuric acid; nitric acid at 5 - 10℃; for 0.5h; | 80% |
10,10-dimethyl-9,10-dihydroanthracen-9-one
4-(diphenylamino)phenyl boronic acid
Conditions | Yield |
---|---|
Stage #1: 10,10-dimethyl-9,10-dihydroanthracen-9-one With toluene-4-sulfonic acid hydrazide In toluene at 80℃; for 2h; Stage #2: 4-(diphenylamino)phenyl boronic acid With potassium carbonate In toluene at 110℃; for 5h; | 80% |
10,10-dimethyl-9,10-dihydroanthracen-9-one
4-(di-naphthalene-2-yl-amino)-phenylboronic acid
Conditions | Yield |
---|---|
Stage #1: 10,10-dimethyl-9,10-dihydroanthracen-9-one With toluene-4-sulfonic acid hydrazide In toluene at 80℃; for 2h; Stage #2: 4-(di-naphthalene-2-yl-amino)-phenylboronic acid With potassium carbonate In toluene at 110℃; for 5h; | 80% |
10,10-dimethyl-9,10-dihydroanthracen-9-one
(2,6-dimethylphenyl)magnesium bromide
Conditions | Yield |
---|---|
In tetrahydrofuran 1.) RT, 3 h, 2.) 80 deg C, 1 h; | 78% |
Conditions | Yield |
---|---|
Stage #1: C12H8BrClO With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran at -78 - 20℃; for 1h; | 75.8% |
Conditions | Yield |
---|---|
Stage #1: 2-bromo-4-chloro-1-phenoxybenzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667h; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran Stage #3: With sulfuric acid; acetic acid Reflux; | 75.58% |
10,10-dimethyl-9,10-dihydroanthracen-9-one
N,N-dimethylethylenediamine
N'-(10,10-Dimethyl-10H-anthracen-9-ylidene)-N,N-dimethyl-ethane-1,2-diamine
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; titanium tetrachloride In benzene for 144h; Ambient temperature; | 69% |
10,10-dimethyl-9,10-dihydroanthracen-9-one
Conditions | Yield |
---|---|
With water-d2; magnesium; ethylene dibromide In tetrahydrofuran at 70℃; for 2h; Inert atmosphere; Schlenk technique; | 69% |
With water-d2; magnesium; ethylene dibromide In tetrahydrofuran | 69% |
The cas register number of 10,10-Dimethylanthrone is 5447-86-9. It also can be called as 9(10H)-anthracenone, 10,10-dimethyl- and the systematic name about this chemical is 10,10-dimethylanthracen-9-one.
Physical properties about 10,10-Dimethylanthrone are: (1)ACD/LogP: 4.61 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): 4.61 ; (4)ACD/LogD (pH 7.4): 4.61 ; (5)ACD/BCF (pH 5.5): 1873.07; (6)ACD/BCF (pH 7.4): 1873.07; (7)ACD/KOC (pH 5.5): 7657.57; (8)ACD/KOC (pH 7.4): 7657.57; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 17.07Å2; (13)Index of Refraction: 1.59; (14)Molar Refractivity: 67.85 cm3; (15)Molar Volume: 200.9 cm3; (16)Surface Tension: 40.2 dyne/cm; (17)Density: 1.105 g/cm3; (18)Flash Point: 149.4 °C; (19)Enthalpy of Vaporization: 59.08 kJ/mol; (20)Boiling Point: 346.6 °C at 760 mmHg; (21)Vapour Pressure: 5.68E-05 mmHg at 25°C.
People can use the following data to convert to the molecule structure.
1.SMILES: O=C2c1c(cccc1)C(c3c2cccc3)(C)C
2.InChI: InChI=1/C16H14O/c1-16(2)13-9-5-3-7-11(13)15(17)12-8-4-6-10-14(12)16/h3-10H,1-2H3
3.InChIKey: GWFCYDIAPRIMLA-UHFFFAOYAU
4.Std. InChI: InChI=1S/C16H14O/c1-16(2)13-9-5-3-7-11(13)15(17)12-8-4-6-10-14(12)16/h3-10H,1-2H3
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