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5,6-Acenaphthylenedicarboxamide,1,2-dihydro-N5,N5,N6,N6-tetramethyl- is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

31458-06-7

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31458-06-7 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 31458-06-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,1,4,5 and 8 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 31458-06:
(7*3)+(6*1)+(5*4)+(4*5)+(3*8)+(2*0)+(1*6)=97
97 % 10 = 7
So 31458-06-7 is a valid CAS Registry Number.

31458-06-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-N,5-N,6-N,6-N-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

1.2 Other means of identification

Product number -
Other names N,N,N',N'-tetramethyl-5,6-acenaphthylenedicarbamide

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:31458-06-7 SDS

31458-06-7Synthetic route

acenaphthene
83-32-9

acenaphthene

N,N-Dimethylcarbamoyl chloride
79-44-7

N,N-Dimethylcarbamoyl chloride

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

Conditions
ConditionsYield
With aluminum (III) chloride In chlorobenzene at 80℃; for 5h; Friedel Crafts acylation; Inert atmosphere; Reflux;73%
With aluminum (III) chloride In chlorobenzene at 0 - 80℃; Inert atmosphere;66.7%
With aluminum (III) chloride In chlorobenzene at 0℃; Time; Inert atmosphere; Reflux;66.7%
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

N5,N5,N6,N6-tetramethylacenaphthylene-5,6-dicarboxamide

N5,N5,N6,N6-tetramethylacenaphthylene-5,6-dicarboxamide

Conditions
ConditionsYield
Stage #1: N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide With N-Bromosuccinimide; dibenzoyl peroxide In chloroform for 2h; Reflux;
Stage #2: With zinc In ethanol for 1h; Reflux;
99%
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

3,8-dibromo-N5,N5,N6,N6-tetramethylacenaphthylene-5,6-dicarboxamide

3,8-dibromo-N5,N5,N6,N6-tetramethylacenaphthylene-5,6-dicarboxamide

Conditions
ConditionsYield
Stage #1: N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide With iron(III) chloride; bromine; sodium hydrogencarbonate In dichloromethane at -15℃; for 12h; Inert atmosphere; Reflux;
Stage #2: With zinc In acetone for 2h; Reflux;
94%
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

1,2-dihydro-6-oxacyclopentaphenalene-5,7-dione
5699-00-3

1,2-dihydro-6-oxacyclopentaphenalene-5,7-dione

Conditions
ConditionsYield
With hydrogenchloride In water Reflux;68.7%
With hydrogenchloride; water Reflux;68.7%
With hydrogenchloride In water at 60℃; for 3.5h;47%
4-lithio-2,6-di-tert-butylphenol
802016-66-6

4-lithio-2,6-di-tert-butylphenol

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

[6-(3,5-di-tert-butyl-4-hydroxy-benzoyl)-acenaphthen-5-yl]-(3,5-di-tert-butyl-4-hydroxy-phenyl)-methanone
876068-20-1

[6-(3,5-di-tert-butyl-4-hydroxy-benzoyl)-acenaphthen-5-yl]-(3,5-di-tert-butyl-4-hydroxy-phenyl)-methanone

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine In diethyl ether at 0 - 20℃;12%
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

5,6-acenaphthenedicarboxylic acid
5698-99-7

5,6-acenaphthenedicarboxylic acid

Conditions
ConditionsYield
With hydrogenchloride
With hydrogenchloride In water for 2h; Reflux;
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

1,2-Dibrom-acenaphthylen-5,6-dicarbonsaeure-dimethylamid
13094-92-3

1,2-Dibrom-acenaphthylen-5,6-dicarbonsaeure-dimethylamid

Conditions
ConditionsYield
With N-Bromosuccinimide; benzoic acid anhydride
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

C28H25N3O2
1417365-38-8

C28H25N3O2

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogenchloride / water / 3.5 h / 60 °C
2: ethanol / Inert atmosphere; Reflux
3: benzeneseleninic anhydride / chlorobenzene / 48 h / 130 °C
4: toluene-4-sulfonic acid / chloroform / 20 °C / Inert atmosphere
View Scheme
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

C50H44N6O4
1417365-40-2

C50H44N6O4

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogenchloride / water / 3.5 h / 60 °C
2: ethanol / Inert atmosphere; Reflux
3: benzeneseleninic anhydride / chlorobenzene / 48 h / 130 °C
4: pyridine / 90 °C / Inert atmosphere
View Scheme
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

2-(2-ethylhexyl)-6,7-dihydro-1H-indeno[6,7,1-def]isoquinoline-1,3(2H)-dione
1417365-45-7

2-(2-ethylhexyl)-6,7-dihydro-1H-indeno[6,7,1-def]isoquinoline-1,3(2H)-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water / 3.5 h / 60 °C
2: ethanol / Inert atmosphere; Reflux
View Scheme
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

2-(2-ethylhexyl)-1H-indeno[6,7,1-def]isoquinoline-1,3,6,7(2H)-tetraone
1417365-46-8

2-(2-ethylhexyl)-1H-indeno[6,7,1-def]isoquinoline-1,3,6,7(2H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / water / 3.5 h / 60 °C
2: ethanol / Inert atmosphere; Reflux
3: benzeneseleninic anhydride / chlorobenzene / 48 h / 130 °C
View Scheme
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

N-(2-hexyldecyl)-1,2-dihydroacenaphthylene dicarboxylic acid imide
1443122-09-5

N-(2-hexyldecyl)-1,2-dihydroacenaphthylene dicarboxylic acid imide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water / Reflux
2: N,N-dimethyl-formamide / 24 h / 90 - 110 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride; water / Reflux
2: N,N-dimethyl-formamide / 24 h / 90 - 110 °C / Inert atmosphere
View Scheme
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

2-(2-hexyldecyl)-1H-indeno[6,7,1-def]isoquinoline-1,3,6,7(2H)-tetraone
1443122-11-9

2-(2-hexyldecyl)-1H-indeno[6,7,1-def]isoquinoline-1,3,6,7(2H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / water / Reflux
2: N,N-dimethyl-formamide / 24 h / 90 - 110 °C / Inert atmosphere
3: acetic anhydride; chromium(VI) oxide / 4 h / 50 - 80 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride; water / Reflux
2: N,N-dimethyl-formamide / 24 h / 90 - 110 °C / Inert atmosphere
3: chromium(VI) oxide; acetic anhydride / 4 h / 20 - 110 °C
View Scheme
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

C66H76N6O4
1443122-12-0

C66H76N6O4

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogenchloride / water / Reflux
2: N,N-dimethyl-formamide / 24 h / 90 - 110 °C / Inert atmosphere
3: acetic anhydride; chromium(VI) oxide / 4 h / 50 - 80 °C
4: potassium carbonate / ethanol / 2 h / 78 °C
View Scheme
Multi-step reaction with 4 steps
1: hydrogenchloride; water / Reflux
2: N,N-dimethyl-formamide / 24 h / 90 - 110 °C / Inert atmosphere
3: chromium(VI) oxide; acetic anhydride / 4 h / 20 - 110 °C
4: potassium carbonate / ethanol / 50 h / 78 °C
View Scheme
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

N-decyltetradecyl-1,2-dihydroacenaphthylenedicarboxylic acid imide
1443122-14-2

N-decyltetradecyl-1,2-dihydroacenaphthylenedicarboxylic acid imide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water / Reflux
2: N,N-dimethyl-formamide / 24 h / 90 - 110 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride; water / Reflux
2: N,N-dimethyl-formamide / 24 h / 90 - 110 °C / Inert atmosphere
View Scheme
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

2-(2-decyltetradecyl)-1H-indeno[6,7,1-def]isoquinoline-1,3,6,7(2H)-tetraone
1443122-16-4

2-(2-decyltetradecyl)-1H-indeno[6,7,1-def]isoquinoline-1,3,6,7(2H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / water / Reflux
2: N,N-dimethyl-formamide / 24 h / 90 - 110 °C / Inert atmosphere
3: acetic anhydride; chromium(VI) oxide / 4 h / 50 - 80 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride; water / Reflux
2: N,N-dimethyl-formamide / 24 h / 90 - 110 °C / Inert atmosphere
3: chromium(VI) oxide; acetic anhydride / 4 h / 20 - 110 °C
View Scheme
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

C65H75N7O4
1569786-08-8

C65H75N7O4

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogenchloride; water / Reflux
2: N,N-dimethyl-formamide / 24 h / 90 - 110 °C / Inert atmosphere
3: chromium(VI) oxide; acetic anhydride / 4 h / 20 - 110 °C
4: ethanol / 78 °C
View Scheme
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

C30H39NO3
1569785-88-1

C30H39NO3

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride; water / Reflux
2: N,N-dimethyl-formamide / 24 h / 90 - 110 °C / Inert atmosphere
3: chromium(VI) oxide; acetic anhydride / acetic anhydride / 20 - 110 °C
View Scheme
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

C60H77N3O2S2
1569787-05-8

C60H77N3O2S2

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogenchloride; water / Reflux
2: N,N-dimethyl-formamide / 24 h / 90 - 110 °C / Inert atmosphere
3: chromium(VI) oxide; acetic anhydride / acetic anhydride / 20 - 110 °C
4: bis(dibenzylideneacetone)-palladium(0) / 48 h / 100 - 110 °C / Inert atmosphere
View Scheme
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

C60H75Br2N3O2S2
1569787-08-1

C60H75Br2N3O2S2

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: hydrogenchloride; water / Reflux
2: N,N-dimethyl-formamide / 24 h / 90 - 110 °C / Inert atmosphere
3: chromium(VI) oxide; acetic anhydride / acetic anhydride / 20 - 110 °C
4: bis(dibenzylideneacetone)-palladium(0) / 48 h / 100 - 110 °C / Inert atmosphere
5: N-Bromosuccinimide / chloroform / 20 - 50 °C
View Scheme
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

N3,N3,N4,N4-tetramethyl-8H-acenaphtho[1,2-c]pyrrole-3,4-dicarboxamide

N3,N3,N4,N4-tetramethyl-8H-acenaphtho[1,2-c]pyrrole-3,4-dicarboxamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 2 h / Reflux
1.2: 1 h / Reflux
2.1: iodine / dichloromethane; water / 17 h / 20 °C
2.2: 1 h / 20 °C
3.1: potassium tert-butylate / tetrahydrofuran; 2-methyltetrahydrofuran / 4 h / 0 °C / Inert atmosphere
3.2: 0.33 h / 80 °C
4.1: potassium tert-butylate / ethylene glycol / 2 h / 196 °C / Inert atmosphere
View Scheme
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

1,1'-(8H-acenaphtho[1,2-c]pyrrole-3,4-diyl)bis(N,N-dimethylmethanamine)

1,1'-(8H-acenaphtho[1,2-c]pyrrole-3,4-diyl)bis(N,N-dimethylmethanamine)

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 2 h / Reflux
1.2: 1 h / Reflux
2.1: iodine / dichloromethane; water / 17 h / 20 °C
2.2: 1 h / 20 °C
3.1: potassium tert-butylate / tetrahydrofuran; 2-methyltetrahydrofuran / 4 h / 0 °C / Inert atmosphere
3.2: 0.33 h / 80 °C
4.1: potassium tert-butylate / ethylene glycol / 2 h / 196 °C / Inert atmosphere
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere; Reflux
View Scheme
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

2-(2,6-diisopropylphenyl)pyrrolo[3',4':2,3]indeno[6,7,1-def]isoquinoline-1,3(2H,7H)-dione

2-(2,6-diisopropylphenyl)pyrrolo[3',4':2,3]indeno[6,7,1-def]isoquinoline-1,3(2H,7H)-dione

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 2 h / Reflux
1.2: 1 h / Reflux
2.1: iodine / dichloromethane; water / 17 h / 20 °C
2.2: 1 h / 20 °C
3.1: potassium tert-butylate / tetrahydrofuran; 2-methyltetrahydrofuran / 4 h / 0 °C / Inert atmosphere
3.2: 0.33 h / 80 °C
4.1: potassium tert-butylate / ethylene glycol / 2 h / 196 °C / Inert atmosphere
5.1: acetic acid / 17 h / 160 °C / Inert atmosphere; Sealed tube
View Scheme
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

1H-pyrano[3',4',5':5,6]acenaphtho[1,2-c]pyrrole-1,3(7H)-dione

1H-pyrano[3',4',5':5,6]acenaphtho[1,2-c]pyrrole-1,3(7H)-dione

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 2 h / Reflux
1.2: 1 h / Reflux
2.1: iodine / dichloromethane; water / 17 h / 20 °C
2.2: 1 h / 20 °C
3.1: potassium tert-butylate / tetrahydrofuran; 2-methyltetrahydrofuran / 4 h / 0 °C / Inert atmosphere
3.2: 0.33 h / 80 °C
4.1: potassium tert-butylate / ethylene glycol / 2 h / 196 °C / Inert atmosphere
5.1: acetic acid / 0.17 h / 170 °C / Inert atmosphere; Sealed tube
View Scheme
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

2-(2,6-diisopropylphenyl)-7-(2-ethylbutyl)pyrrolo[3',4':2,3]indeno[6,7,1-def]isoquinoline-1,3(2H,7H)-dione

2-(2,6-diisopropylphenyl)-7-(2-ethylbutyl)pyrrolo[3',4':2,3]indeno[6,7,1-def]isoquinoline-1,3(2H,7H)-dione

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 2 h / Reflux
1.2: 1 h / Reflux
2.1: iodine / dichloromethane; water / 17 h / 20 °C
2.2: 1 h / 20 °C
3.1: potassium tert-butylate / tetrahydrofuran; 2-methyltetrahydrofuran / 4 h / 0 °C / Inert atmosphere
3.2: 0.33 h / 80 °C
4.1: potassium tert-butylate / ethylene glycol / 2 h / 196 °C / Inert atmosphere
5.1: acetic acid / 17 h / 160 °C / Inert atmosphere; Sealed tube
6.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.33 h / 0 °C
6.2: 2 h / 20 °C
View Scheme
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

dimethyl 8H-acenaphtho[1,2-c]pyrrole-3,4-dicarboxylate

dimethyl 8H-acenaphtho[1,2-c]pyrrole-3,4-dicarboxylate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 2 h / Reflux
1.2: 1 h / Reflux
2.1: iodine / dichloromethane; water / 17 h / 20 °C
2.2: 1 h / 20 °C
3.1: potassium tert-butylate / tetrahydrofuran; 2-methyltetrahydrofuran / 4 h / 0 °C / Inert atmosphere
3.2: 0.33 h / 80 °C
4.1: potassium tert-butylate / ethylene glycol / 2 h / 196 °C / Inert atmosphere
5.1: acetic acid / 0.17 h / 170 °C / Inert atmosphere; Sealed tube
6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 4 h / 70 °C / Inert atmosphere
View Scheme
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

benzo[4,5]imidazo[2,1-a]pyrrolo[3',4':2,3]indeno[6,7,1-def]isoquinolin-6(2H)-one

benzo[4,5]imidazo[2,1-a]pyrrolo[3',4':2,3]indeno[6,7,1-def]isoquinolin-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 2 h / Reflux
1.2: 1 h / Reflux
2.1: iodine / dichloromethane; water / 17 h / 20 °C
2.2: 1 h / 20 °C
3.1: potassium tert-butylate / tetrahydrofuran; 2-methyltetrahydrofuran / 4 h / 0 °C / Inert atmosphere
3.2: 0.33 h / 80 °C
4.1: potassium tert-butylate / ethylene glycol / 2 h / 196 °C / Inert atmosphere
5.1: acetic acid / 0.17 h / 170 °C / Inert atmosphere; Sealed tube
6.1: zinc(II) chloride / quinoline / 3 h / 230 °C / Inert atmosphere
View Scheme
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

naphtho[2',3':4,5]imidazo[2,1-a]pyrrolo[3',4':2,3]indeno[6,7,1-def]isoquinolin-6(2H)-one

naphtho[2',3':4,5]imidazo[2,1-a]pyrrolo[3',4':2,3]indeno[6,7,1-def]isoquinolin-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 2 h / Reflux
1.2: 1 h / Reflux
2.1: iodine / dichloromethane; water / 17 h / 20 °C
2.2: 1 h / 20 °C
3.1: potassium tert-butylate / tetrahydrofuran; 2-methyltetrahydrofuran / 4 h / 0 °C / Inert atmosphere
3.2: 0.33 h / 80 °C
4.1: potassium tert-butylate / ethylene glycol / 2 h / 196 °C / Inert atmosphere
5.1: acetic acid / 0.17 h / 170 °C / Inert atmosphere; Sealed tube
6.1: zinc(II) chloride / quinoline / 4 h / 180 °C / Inert atmosphere
View Scheme
N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide
31458-06-7

N5,N5,N6,N6-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

6,6-difluoro-6,11-dihydro-15H-5λ4,6λ4-pyrrolo[3''',4''':4'',5'']cyclopenta[1'',2'',3'':6',7']phenaleno[2',1':5,6][1,3,2]oxazaborinino[3,4-a]quinolin-15-one

6,6-difluoro-6,11-dihydro-15H-5λ4,6λ4-pyrrolo[3''',4''':4'',5'']cyclopenta[1'',2'',3'':6',7']phenaleno[2',1':5,6][1,3,2]oxazaborinino[3,4-a]quinolin-15-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 2 h / Reflux
1.2: 1 h / Reflux
2.1: iodine / dichloromethane; water / 17 h / 20 °C
2.2: 1 h / 20 °C
3.1: potassium tert-butylate / tetrahydrofuran; 2-methyltetrahydrofuran / 4 h / 0 °C / Inert atmosphere
3.2: 0.33 h / 80 °C
4.1: potassium tert-butylate / ethylene glycol / 2 h / 196 °C / Inert atmosphere
5.1: acetic acid / 0.17 h / 170 °C / Inert atmosphere; Sealed tube
6.1: zinc(II) chloride / quinoline / 3 h / 200 °C / Inert atmosphere
6.2: 2.5 h / 60 °C / Inert atmosphere
View Scheme

31458-06-7Relevant academic research and scientific papers

Tetraazabenzodifluoranthene diimides: Building blocks for solution-processable n-type organic semiconductors

Li, Haiyan,Kim, Felix Sunjoo,Ren, Guoqiang,Hollenbeck, Emily C.,Subramaniyan, Selvam,Jenekhe, Samson A.

, p. 5513 - 5517 (2013)

11-Ring heterocyclic diimides were synthesized and found to be planar and to exhibit a slipped face-to-face πstacking. Variation of the substituents tunes the electronic structure and properties. In n-channel organic field-effect transistors, the new organic semiconductors have a high electron mobility. When they were used as acceptor material in polymer solar cells, a power conversion efficiency of 1.8 % was obtained. Copyright

Bandgap Engineering in π-Extended Pyrroles. A Modular Approach to Electron-Deficient Chromophores with Multi-Redox Activity

Zhylitskaya, Halina,Cybińska, Joanna,Chmielewski, Piotr,Lis, Tadeusz,St?pień, Marcin

, p. 11390 - 11398 (2016)

A family of bandgap-tunable pyrroles structurally related to rylene dyes was computationally designed and prepared using robust, easily scalable chemistry. These pyrroles show highly variable fluorescence properties and can be used as building blocks for the synthesis of electron-deficient oligopyrroles. The latter application is demonstrated through the development of π-extended porphyrins containing naphthalenediamide or naphthalenediimide units. These new macrocycles exhibit simultaneously tunable visible and near-IR absorptions, an ability to accept up to 8 electrons via electrochemical reduction, and high internal molecular free volumes. When chemically reduced under inert conditions, the most electron-deficient of these macrocycles revealed reversible formation of eight charged states, characterized by remarkably red-shifted optical absorptions, extending beyond 2200 nm. Such features make these oligopyrroles of interest as functional chromophores, charge-storage materials, and tectons for crystal engineering.

Linear and star-shaped naphthalimide-fused pyrazinacenes

Herrera, Helena,De Echegaray, Paula,Urdanpilleta, Marta,Mancheno, Maria J.,Mena-Osteritz, Elena,Baeuerle, Peter,Segura, Jose L.

, p. 713 - 715 (2013)

A novel naphthalimide derivative endowed with a diketone functionality has been synthesized and used to develop a family of highly symmetric, flat, n-type semiconducting naphthalimide-based pyrazinacenes. By changing the symmetry of these compounds and the number of naphthalimide constituents, fine tuning of their electrochemical, photophysical, and morphological properties is achieved.

ACENAPHTHYLENE IMIDE-DERIVED SEMICONDUCTORS

-

Page/Page column 39; 40, (2014/03/25)

Novel acenaphthylene imide-derived semiconductor materials, including small molecule compounds, polymers and oligomers. Also provided are methods for making the novel semiconductor materials and the use of the novel semiconducting materials in electronic or optoelectronic device. In some embodiments, the novel semiconducting materials are used as n-channel component in organic field-effect transistors as well as complementary electronic circuits including inverters. High mobility can be achieved.

Synthesis of two complementary molecular moulds

Barattin, Regis,Gourdon, Andre

supporting information; experimental part, p. 1022 - 1026 (2009/07/19)

The synthesis of two complementary molecular moulds is described. These molecules comprise a polyaromatic central part and four lateral bulky tert-butylphenyl or di-tertbutylphenyl groups so that when they are deposited onto a surface, a cavity prone to metallic moulding is created.

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