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5447-86-9

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5447-86-9 Usage

Chemical Properties

Light Yellow Solid

Uses

Derivative of Anthrone

Check Digit Verification of cas no

The CAS Registry Mumber 5447-86-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,4,4 and 7 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 5447-86:
(6*5)+(5*4)+(4*4)+(3*7)+(2*8)+(1*6)=109
109 % 10 = 9
So 5447-86-9 is a valid CAS Registry Number.
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

5447-86-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 10,10-Dimethylanthrone

1.2 Other means of identification

Product number -
Other names 10,10-dimethylanthracen-9-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5447-86-9 SDS

5447-86-9Synthetic route

9,9-Dimethyl-10-(trimethylsilyl)-9,10-dihydroanthracene
136590-96-0

9,9-Dimethyl-10-(trimethylsilyl)-9,10-dihydroanthracene

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

Conditions
ConditionsYield
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
85199-64-0

9-diazo-10,10-dimethyl-9,10-dihydroanthracene

A

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

B

10-[10,10-dimethyl-9(10H)-anthracenyl]-9,10-dihydro-9,9-dimethylanthracene
85199-69-5

10-[10,10-dimethyl-9(10H)-anthracenyl]-9,10-dihydro-9,9-dimethylanthracene

Conditions
ConditionsYield
With (Z)-2-Butene Irradiation;A 8%
B 80%
9,10-Dihydro-10,10-dimethylanthracen
42332-94-5

9,10-Dihydro-10,10-dimethylanthracen

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

Conditions
ConditionsYield
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
80716-32-1

(8aR,9R)-8a,9-Dimethyl-8a,9-dihydro-anthracen-9-ol

A

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

B

9,10-Dihydro-10,10-dimethylanthracen
42332-94-5

9,10-Dihydro-10,10-dimethylanthracen

Conditions
ConditionsYield
With sulfuric acid; acetic anhydride In acetic acidA 25%
B 53%
9,9a-dihydro-9,9a-dimethyl-9-anthracenol
80716-32-1

9,9a-dihydro-9,9a-dimethyl-9-anthracenol

A

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

B

9,10-Dihydro-10,10-dimethylanthracen
42332-94-5

9,10-Dihydro-10,10-dimethylanthracen

Conditions
ConditionsYield
With sulfuric acid; acetic anhydride In acetic acid at 23℃; for 2.25h;A 25%
B 53%
acetic anhydride
108-24-7

acetic anhydride

9,9a-dihydro-9,9a-dimethyl-9-anthracenol
80716-32-1

9,9a-dihydro-9,9a-dimethyl-9-anthracenol

A

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

B

9,10-Dihydro-10,10-dimethylanthracen
42332-94-5

9,10-Dihydro-10,10-dimethylanthracen

C

10,10-dimethyl-9,10-dihydroanthranylacetic acid
80716-37-6

10,10-dimethyl-9,10-dihydroanthranylacetic acid

Conditions
ConditionsYield
With sulfuric acid for 2h; Yields of byproduct given;A n/a
B n/a
C 45%
dimethylketene
598-26-5

dimethylketene

N-(10,10-dimethyl-9,10-dihydroanthracen-9-ylidene)phenylamine N-oxide
101023-20-5

N-(10,10-dimethyl-9,10-dihydroanthracen-9-ylidene)phenylamine N-oxide

A

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

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
101023-21-6

4',4',10,10-tetramethyl-3'-phenyl-9,10-dihydroanthracene-9-spiro-2'-oxazolidin-5'-one

Conditions
ConditionsYield
In ethyl acetate Ambient temperature;A 150 mg
B 24%
2-(1-hydroxy-1-methyl-ethyl)-benzophenone cyclohemiacetal
1023-91-2

2-(1-hydroxy-1-methyl-ethyl)-benzophenone cyclohemiacetal

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

Conditions
ConditionsYield
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
80716-32-1

(8aR,9R)-8a,9-Dimethyl-8a,9-dihydro-anthracen-9-ol

A

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

B

9,10-Dihydro-10,10-dimethylanthracen
42332-94-5

9,10-Dihydro-10,10-dimethylanthracen

C

10,10-dimethyl-9,10-dihydroanthranylacetic acid
80716-37-6

10,10-dimethyl-9,10-dihydroanthranylacetic acid

Conditions
ConditionsYield
A 10%
B 15%
C 75 % Spectr.
anthracen-9(10H)-one
90-44-8

anthracen-9(10H)-one

methyl iodide
74-88-4

methyl iodide

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

Conditions
ConditionsYield
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.
9-anthrol
529-86-2

9-anthrol

methyl iodide
74-88-4

methyl iodide

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

Conditions
ConditionsYield
Lithium-Verbindung;
With water; potassium carbonate
anthracen-9(10H)-one
90-44-8

anthracen-9(10H)-one

methyl iodide
74-88-4

methyl iodide

A

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

B

methyl-9-methoxy-10-anthracene
21992-33-6

methyl-9-methoxy-10-anthracene

Conditions
ConditionsYield
With potassium hydroxide
o-Isopropylbenzophenon-oxim
71104-02-4

o-Isopropylbenzophenon-oxim

chloroacetic acid
79-11-8

chloroacetic acid

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

Conditions
ConditionsYield
(i) NaOH, aq. EtOH, (ii) K2S2O8, aq. NaOH; Multistep reaction;
9,10-dihydro-10,10-dimethyl-9-anthracenol
18792-73-9

9,10-dihydro-10,10-dimethyl-9-anthracenol

A

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

B

9,10-Dihydro-10,10-dimethylanthracen
42332-94-5

9,10-Dihydro-10,10-dimethylanthracen

Conditions
ConditionsYield
With sulfuric acid In acetic acid for 3h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
methylene chloride
74-87-3

methylene chloride

10-nitro-9-methylanthracene
84457-22-7

10-nitro-9-methylanthracene

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

Conditions
ConditionsYield
Yield given. Multistep reaction;
9,10-dihydro-10,10-dimethyl-9-anthracenol
18792-73-9

9,10-dihydro-10,10-dimethyl-9-anthracenol

acetic anhydride
108-24-7

acetic anhydride

A

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

B

9,10-Dihydro-10,10-dimethylanthracen
42332-94-5

9,10-Dihydro-10,10-dimethylanthracen

C

10,10-dimethyl-9,10-dihydroanthranylacetic acid
80716-37-6

10,10-dimethyl-9,10-dihydroanthranylacetic acid

Conditions
ConditionsYield
With sulfuric acid for 2h; Yields of byproduct given;
anthracen-9(10H)-one
90-44-8

anthracen-9(10H)-one

methyl iodide
74-88-4

methyl iodide

A

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

B

methyl-9-methoxy-10-anthracene
21992-33-6

methyl-9-methoxy-10-anthracene

C

9-methoxyanthracene
2395-96-2

9-methoxyanthracene

D

9,10-phenanthrenequinone
84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
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;
anthracen-9(10H)-one
90-44-8

anthracen-9(10H)-one

methanol. lithium methylate

methanol. lithium methylate

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

Conditions
ConditionsYield
With toluene Erhitzen des Reaktionsprodukts mit CH3I und wenig tert-Butylalkohol;
anthracen-9(10H)-one
90-44-8

anthracen-9(10H)-one

methyl iodide
74-88-4

methyl iodide

KOH-solution

KOH-solution

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

3,3-Dimethyl-3H-isobenzofuran-1-one
1689-09-4

3,3-Dimethyl-3H-isobenzofuran-1-one

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

Conditions
ConditionsYield
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
80716-28-5

9a-hydro-9a-methyl-9-anthracenone

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

Conditions
ConditionsYield
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
85199-72-0

C23H22N2O2S

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 77 percent / sodium methoxide / pyridine / 70 °C
2: 8 percent / cis-2-butene / Irradiation
View Scheme
9-nitroanthracene
602-60-8

9-nitroanthracene

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

1,4,9a-trihydro-9a-methyl-9-anthracenone
80716-26-3

1,4,9a-trihydro-9a-methyl-9-anthracenone

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

Conditions
ConditionsYield
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
80716-27-4

1,2,9a-trihydro-9a-methyl-9-anthracenone

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

Conditions
ConditionsYield
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
phthalic anhydride
85-44-9

phthalic anhydride

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

Conditions
ConditionsYield
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
10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

3-(Dimethylamino)propyl chloride
109-54-6

3-(Dimethylamino)propyl chloride

C20H25NO

C20H25NO

Conditions
ConditionsYield
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
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

10,10-dimethylanthrone hydrazone
90624-29-6

10,10-dimethylanthrone hydrazone

Conditions
ConditionsYield
With hydrazine hydrochloride; hydrazine hydrate In various solvent(s) Heating;95%
With hydrazinium sulfate; hydrazine Heating; Yield given;
10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

9,10-Dibromoanthracene
523-27-3

9,10-Dibromoanthracene

10′-bromo-10,10-dimethyl-[9,9′-bianthracen]-9(10H)-ol

10′-bromo-10,10-dimethyl-[9,9′-bianthracen]-9(10H)-ol

Conditions
ConditionsYield
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
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

(4-bromophenyl)magnesium bromide
18620-02-5

(4-bromophenyl)magnesium bromide

C22H19BrO

C22H19BrO

Conditions
ConditionsYield
In tetrahydrofuran at 60℃; for 24h; Grignard Reaction;88%
10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

C22H19BrO

C22H19BrO

Conditions
ConditionsYield
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
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

9,10-Dihydro-10,10-dimethylanthracen
42332-94-5

9,10-Dihydro-10,10-dimethylanthracen

Conditions
ConditionsYield
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
955959-84-9

4-(4-bromophenyl)dibenzofuran

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

C34H26O2

C34H26O2

Conditions
ConditionsYield
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
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

4-(2-bromo-4-chlorophenyl)dibenzofuran

4-(2-bromo-4-chlorophenyl)dibenzofuran

9-(5-chloro-2-(dibenzofuran-4-yl)phenyl)-10,10-dimethyl-9,10-dihydroanthracen-9-ol

9-(5-chloro-2-(dibenzofuran-4-yl)phenyl)-10,10-dimethyl-9,10-dihydroanthracen-9-ol

Conditions
ConditionsYield
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
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

(4-(di([1,1’-biphenyl]-4-yl)amino)phenyl)boronic acid
943836-24-6

(4-(di([1,1’-biphenyl]-4-yl)amino)phenyl)boronic acid

C46H37N

C46H37N

Conditions
ConditionsYield
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%
10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

C44H39BN2O2

C44H39BN2O2

C60H52N2

C60H52N2

Conditions
ConditionsYield
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%
10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

C32H24BNO2

C32H24BNO2

C48H37N

C48H37N

Conditions
ConditionsYield
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
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

2-bromo-10,10-dimethyl-10H-anthracen-9-one

2-bromo-10,10-dimethyl-10H-anthracen-9-one

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 18h; Darkness;83%
10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

1-Bromo-5-chloronaphthalene
77332-65-1

1-Bromo-5-chloronaphthalene

C26H21ClO

C26H21ClO

Conditions
ConditionsYield
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%
10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

2-bromo-7-chloronaphthalene

2-bromo-7-chloronaphthalene

C26H21ClO

C26H21ClO

Conditions
ConditionsYield
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%
2-(4-bromophenyl]pyridine
63996-36-1

2-(4-bromophenyl]pyridine

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

C27H23NO

C27H23NO

Conditions
ConditionsYield
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
108-86-1

bromobenzene

10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

10,10-dimethyl-9-phenyl-9,10-dihydroanthracen-9-ol
39615-41-3

10,10-dimethyl-9-phenyl-9,10-dihydroanthracen-9-ol

Conditions
ConditionsYield
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
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

1-bromo-4-chloronaphthalene
53220-82-9

1-bromo-4-chloronaphthalene

C26H21ClO

C26H21ClO

Conditions
ConditionsYield
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%
10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

C27H25BN2O3

C27H25BN2O3

C43H38N2O

C43H38N2O

Conditions
ConditionsYield
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%
10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

C41H35BN2O2

C41H35BN2O2

C57H48N2

C57H48N2

Conditions
ConditionsYield
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
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

C16H12N2O5

C16H12N2O5

Conditions
ConditionsYield
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
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

4-(diphenylamino)phenyl boronic acid
201802-67-7

4-(diphenylamino)phenyl boronic acid

C34H29N

C34H29N

Conditions
ConditionsYield
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
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

4-(di-naphthalene-2-yl-amino)-phenylboronic acid
1232102-18-9

4-(di-naphthalene-2-yl-amino)-phenylboronic acid

C42H33N

C42H33N

Conditions
ConditionsYield
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
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

(2,6-dimethylphenyl)magnesium bromide
21450-64-6

(2,6-dimethylphenyl)magnesium bromide

9-(2,6-xylyl)-10,10-dimethyl-9,10-dihydroanthracen-9-ol

9-(2,6-xylyl)-10,10-dimethyl-9,10-dihydroanthracen-9-ol

Conditions
ConditionsYield
In tetrahydrofuran 1.) RT, 3 h, 2.) 80 deg C, 1 h;78%
10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

C12H8BrClO

C12H8BrClO

C28H21ClO

C28H21ClO

Conditions
ConditionsYield
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%
10,10-dimethyl-9,10-dihydroanthracen-9-one
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

2-bromo-4-chloro-1-phenoxybenzene

2-bromo-4-chloro-1-phenoxybenzene

C28H21ClO

C28H21ClO

Conditions
ConditionsYield
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
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

N,N-dimethylethylenediamine
108-00-9

N,N-dimethylethylenediamine

N'-(10,10-Dimethyl-10H-anthracen-9-ylidene)-N,N-dimethyl-ethane-1,2-diamine
76596-08-2

N'-(10,10-Dimethyl-10H-anthracen-9-ylidene)-N,N-dimethyl-ethane-1,2-diamine

Conditions
ConditionsYield
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
5447-86-9

10,10-dimethyl-9,10-dihydroanthracen-9-one

C16H15(2)HO

C16H15(2)HO

Conditions
ConditionsYield
With water-d2; magnesium; ethylene dibromide In tetrahydrofuran at 70℃; for 2h; Inert atmosphere; Schlenk technique;69%
With water-d2; magnesium; ethylene dibromide In tetrahydrofuran69%

5447-86-9Relevant articles and documents

Preparation method of 10,10-dimethylanthrone

-

, (2019/06/30)

The invention belongs to the field of drug synthesis and provides a novel method of synthesizing melitracen hydrochloride intermediate 10,10-dimethylanthrone. The 10,10-dimethylanthrone is prepared from phthalic anhydride as a start material through two-step Grignard reaction and three-step closed-ring reaction. The total yield is up to 30%, and the purity of the finished intermediate is higher than 98.0%. Compared with traditional synthetic processes, the novel process herein has simple steps and greatly reduced production cost, causes little environmental pollution and helps greatly solve the environmental issue caused by the production of 10,10-dimethylanthrone.

Regioselective alkylation of anthrone, 5,5-dimethyl-3-isoxazolidinone and 4-methylquinolone by phase transfer catalysis

Dehmlow, Eckehard Volker,Bollhoefer, Joerg,Thye, Gorden

, p. 113 - 115 (2007/10/03)

Anthrone (1) can be alkylated selectively to give O-, C,O- or C,C-substituted compounds 2, 4, or 5, respectively. Similarly, 5,5-dimethyl-3-isoxazolidinone (6) and 4-methylquinolone (9) yield N- or O-derivatives 7 and 8 or 10 and 11, respectively. The product ratios can be influenced strongly sometimes by use of different phase transfer catalysts, but the sensitivity of each reaction towards the catalysts is unique.

Free energy and entropy changes in vertical and nonvertical triplet energy transfer processes between rigid and nonrigid molecules. A laser photolysis study

Zhang, Daisy,Closs, Gerhard L.,Chung, Dutch D.,Norris, James R.

, p. 3670 - 3673 (2007/10/02)

The free energy and entropy changes associated with intermolecular triplet energy transfer (TT) processes were determined by direct measurement of the equilibrium constant using a laser flash photolysis technique. 10,10-Dimethylanthrone and 9,9-dimethylfluorene were synthesized and used as a "rigid" donor and acceptor, respectively, in comparison with 4-methylbenzophenone, a "nonrigid" donor, and 4-methylbiphenyl, a "nonrigid" acceptor, in the TT reactions. Both the nonrigid donor and the nonrigid acceptor lose entropy while going from the twisted ground state to the planar triplet state. The ΔS values for 4-methylbenzophenone and 4-methylbiphenyl are 0.5-1.0 and 2.5-3.0 gibbs/mol, respectively.

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