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57102-42-8

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57102-42-8 Usage

Description

(9-(4-BROMOPHENYL))-9H-CARBAZOLE is a white to light yellow solid that serves as a crucial intermediate in various applications, including pharmaceuticals, organic synthesis, and organic light-emitting diodes (OLEDs).

Uses

Used in Pharmaceutical Industry:
(9-(4-BROMOPHENYL))-9H-CARBAZOLE is used as an intermediate for the development of new pharmaceutical compounds due to its unique chemical structure and properties, which can be further modified to create potential therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, (9-(4-BROMOPHENYL))-9H-CARBAZOLE is utilized as a key building block for the synthesis of complex organic molecules, contributing to the advancement of chemical research and the development of novel materials.
Used in Organic Light-Emitting Diode (OLED) Industry:
(9-(4-BROMOPHENYL))-9H-CARBAZOLE is employed as an intermediate in the production of organic light-emitting diodes (OLEDs), which are widely used in display technologies and lighting applications. Its properties make it a valuable component in the design and fabrication of OLED devices.

Check Digit Verification of cas no

The CAS Registry Mumber 57102-42-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,7,1,0 and 2 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 57102-42:
(7*5)+(6*7)+(5*1)+(4*0)+(3*2)+(2*4)+(1*2)=98
98 % 10 = 8
So 57102-42-8 is a valid CAS Registry Number.
InChI:InChI=1/C18H12BrN/c19-13-9-11-14(12-10-13)20-17-7-3-1-5-15(17)16-6-2-4-8-18(16)20/h1-12H

57102-42-8 Well-known Company Product Price

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  • Alfa Aesar

  • (H64404)  9-(4-Bromophenyl)carbazole, 98%   

  • 57102-42-8

  • 5g

  • 1547.0CNY

  • Detail
  • Alfa Aesar

  • (H64404)  9-(4-Bromophenyl)carbazole, 98%   

  • 57102-42-8

  • 25g

  • 2342.0CNY

  • Detail

57102-42-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 9-(4-Bromophenyl)carbazole

1.2 Other means of identification

Product number -
Other names 9-(4-bromophenyl)carbazole

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:57102-42-8 SDS

57102-42-8Synthetic route

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

9H-carbazole
86-74-8

9H-carbazole

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In 1,2-dimethoxyethane; water at 95℃; for 20h; Catalytic behavior; Solvent; Schlenk technique; Inert atmosphere; Sealed tube;99%
With copper; potassium carbonate In N,N-dimethyl acetamide at 180℃; for 40h; Schlenk technique; Inert atmosphere;99%
With copper; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 42h; Inert atmosphere;96%
[1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate
189999-35-7

[1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate

4-bromo-aniline
106-40-1

4-bromo-aniline

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

Conditions
ConditionsYield
With copper diacetate; sodium carbonate In ethylene glycol; isopropyl alcohol at 90℃; for 16h;98.46%
With copper diacetate; sodium carbonate; ethylene glycol In isopropyl alcohol at 85℃; for 16h; Ullmann Condensation; Inert atmosphere;65%
With copper diacetate; sodium carbonate In ethylene glycol; isopropyl alcohol for 16h; Inert atmosphere; Reflux; Green chemistry;
9H-carbazole
86-74-8

9H-carbazole

(4-bromophenyl)hydrazine
589-21-9

(4-bromophenyl)hydrazine

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

Conditions
ConditionsYield
With palladium diacetate; cesium fluoride In acetonitrile at 60℃; for 12h; Schlenk technique;96%
9H-carbazole
86-74-8

9H-carbazole

1-Bromo-4-fluorobenzene
460-00-4

1-Bromo-4-fluorobenzene

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 150℃; for 24h;95%
With potassium phosphate In N,N-dimethyl-formamide at 190℃; for 1h; Microwave irradiation;91%
With caesium carbonate In dimethyl sulfoxide at 160℃; for 48h; Inert atmosphere;80%
With potassium fluoride; 18-crown-6 ether In dimethyl sulfoxide for 24h; Reflux;68.3%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;66%
N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

Conditions
ConditionsYield
With N-Bromosuccinimide In chloroform at 20℃; for 24h;91%
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / N,N-dimethyl-formamide / 16 h / 0 °C / Inert atmosphere
2: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tetrakis(acetonitrile)copper(I)tetrafluoroborate; 2.9-dimethyl-1,10-phenanthroline; iodine; methyloxirane / tetrahydrofuran / 21 h / 21 °C / Flow reactor; Irradiation
View Scheme
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

9H-carbazole
86-74-8

9H-carbazole

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; L-proline In dimethyl sulfoxide at 140℃; Ullmann reaction; Inert atmosphere;85%
With copper; potassium carbonate; nitrobenzene at 120 - 160℃; Inert atmosphere;85%
With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane In toluene at 110℃; for 24h; Inert atmosphere; sealed tube;83%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

9H-carbazole
86-74-8

9H-carbazole

A

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

B

9-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazole
19287-68-4

9-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazole

Conditions
ConditionsYield
With copper; potassium carbonate In Triethylene glycol dimethyl ether at 180 - 200℃; for 24h; Ullmann condensation;A 71%
B 28%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 111℃; for 26h; Schlenk technique; Inert atmosphere; chemoselective reaction;A 49%
B 13%
1-azido-4-bromobenzene
2101-88-4

1-azido-4-bromobenzene

2-Biphenylboronic acid
4688-76-0

2-Biphenylboronic acid

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

Conditions
ConditionsYield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; sodium carbonate In 1,4-dioxane at 80℃; for 12h; Schlenk technique;70%
2-iodobiphenyl
2113-51-1

2-iodobiphenyl

4-bromo-aniline
106-40-1

4-bromo-aniline

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

Conditions
ConditionsYield
With copper diacetate; palladium diacetate; caesium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 120℃; for 12h; Sealed tube;48%
N-N'-dimetylpropyleneurea

N-N'-dimetylpropyleneurea

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

copper(I) iodide
7681-65-4

copper(I) iodide

9H-carbazole
86-74-8

9H-carbazole

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

Conditions
ConditionsYield
With potassium carbonate; 18-crown-6 ether35%
1,3,4-trimethylimidazolidin-2-one
24044-24-4

1,3,4-trimethylimidazolidin-2-one

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

9H-carbazole
86-74-8

9H-carbazole

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

Conditions
ConditionsYield
With potassium carbonate; 18-crown-6 ether; copper(I) iodide35%
9H-carbazole
86-74-8

9H-carbazole

1,2-dibromobenzene
583-53-9

1,2-dibromobenzene

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

Conditions
ConditionsYield
With potassium carbonate; copper(II) sulfate at 210℃; Inert atmosphere;31%
4-N,N-diphenylamino-1-bromobenzene
36809-26-4

4-N,N-diphenylamino-1-bromobenzene

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

Conditions
ConditionsYield
With tetrakis(acetonitrile)copper(I)tetrafluoroborate; 2.9-dimethyl-1,10-phenanthroline; iodine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; methyloxirane In tetrahydrofuran at 21℃; for 21h; Reagent/catalyst; Flow reactor; Irradiation;19%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

9H-carbazole
86-74-8

9H-carbazole

A

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

B

9-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazole
19287-68-4

9-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazole

C

9-(4-iodophenyl)carbazole
57103-15-8

9-(4-iodophenyl)carbazole

Conditions
ConditionsYield
With copper(l) iodide; 18-crown-6 ether; potassium carbonate at 175℃; for 24h; Schlenk technique; Inert atmosphere;A 20 %Spectr.
B 9%
C 33 %Spectr.
1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone
7226-23-5

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

copper(I) iodide
7681-65-4

copper(I) iodide

9H-carbazole
86-74-8

9H-carbazole

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

Conditions
ConditionsYield
With potassium carbonate; 18-crown-6 ether
phenylboronic acid
98-80-6

phenylboronic acid

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / ethanol / 6 h / Reflux; Inert atmosphere
2.1: hydrazine hydrate / methanol / 2 h / 20 °C
3.1: hydrogenchloride; sodium nitrite / tetrahydrofuran; water / 0.33 h / Cooling with ice
3.2: 20 °C / Cooling with ice
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 20 °C
5.1: copper diacetate; sodium carbonate; ethylene glycol / isopropyl alcohol / 16 h / 85 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / ethanol / 6 h / Reflux
2.1: sodium nitrite; hydrogenchloride / water; tetrahydrofuran / 0 °C
2.2: Sandmeyer Reaction / 20 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C
4.1: sodium carbonate; copper diacetate / isopropyl alcohol; ethylene glycol / 16 h / Inert atmosphere; Reflux; Green chemistry
View Scheme
o-nitroiodobenzene
609-73-4

o-nitroiodobenzene

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / ethanol / 6 h / Reflux; Inert atmosphere
2.1: hydrazine hydrate / methanol / 2 h / 20 °C
3.1: hydrogenchloride; sodium nitrite / tetrahydrofuran; water / 0.33 h / Cooling with ice
3.2: 20 °C / Cooling with ice
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 20 °C
5.1: copper diacetate; sodium carbonate; ethylene glycol / isopropyl alcohol / 16 h / 85 °C / Inert atmosphere
View Scheme
2-nitrobiphenyl
86-00-0

2-nitrobiphenyl

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydrazine hydrate / methanol / 2 h / 20 °C
2.1: hydrogenchloride; sodium nitrite / tetrahydrofuran; water / 0.33 h / Cooling with ice
2.2: 20 °C / Cooling with ice
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 20 °C
4.1: copper diacetate; sodium carbonate; ethylene glycol / isopropyl alcohol / 16 h / 85 °C / Inert atmosphere
View Scheme
2-phenylaniline
90-41-5

2-phenylaniline

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride; sodium nitrite / tetrahydrofuran; water / 0.33 h / Cooling with ice
1.2: 20 °C / Cooling with ice
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 20 °C
3.1: copper diacetate; sodium carbonate; ethylene glycol / isopropyl alcohol / 16 h / 85 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: sodium nitrite; hydrogenchloride / water; tetrahydrofuran / 0 °C
1.2: Sandmeyer Reaction / 20 °C
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C
3.1: sodium carbonate; copper diacetate / isopropyl alcohol; ethylene glycol / 16 h / Inert atmosphere; Reflux; Green chemistry
View Scheme
2-iodobiphenyl
2113-51-1

2-iodobiphenyl

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 20 °C
2: copper diacetate; sodium carbonate; ethylene glycol / isopropyl alcohol / 16 h / 85 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C
2: sodium carbonate; copper diacetate / isopropyl alcohol; ethylene glycol / 16 h / Inert atmosphere; Reflux; Green chemistry
View Scheme
2-iodophenylamine
615-43-0

2-iodophenylamine

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / ethanol / 6 h / Reflux
2.1: sodium nitrite; hydrogenchloride / water; tetrahydrofuran / 0 °C
2.2: Sandmeyer Reaction / 20 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C
4.1: sodium carbonate; copper diacetate / isopropyl alcohol; ethylene glycol / 16 h / Inert atmosphere; Reflux; Green chemistry
View Scheme
2-Bromobiphenyl
2052-07-5

2-Bromobiphenyl

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C / Schlenk technique
1.2: 10 h / -78 - 20 °C / Schlenk technique
1.3: 1 h / 20 °C / pH 6 - 7 / Schlenk technique
2.1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; sodium carbonate / 1,4-dioxane / 12 h / 80 °C / Schlenk technique
View Scheme
N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

3-bromo-9-(4-bromophenyl)-9H-carbazole
1226860-66-7

3-bromo-9-(4-bromophenyl)-9H-carbazole

Conditions
ConditionsYield
With N-Bromosuccinimide at 20℃; for 12h; Inert atmosphere;100%
With N-Bromosuccinimide at 20℃;98%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 12.5h;92%
N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

9,9′-bis(4-bromophenyl)-9H,9′H-3,3′-bicarbazole

9,9′-bis(4-bromophenyl)-9H,9′H-3,3′-bicarbazole

Conditions
ConditionsYield
Stage #1: N-(4-bromophenyl)carbazole With methanesulfonic acid In dichloromethane at 0℃; Inert atmosphere;
Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 0.0166667h; Reagent/catalyst; Inert atmosphere; regioselective reaction;
99%
With iron(III) chloride In chloroform at 20℃; for 40h; Inert atmosphere;
N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

9‐(4‐bromophenyl)‐3,6‐diiodocarbazole
601454-29-9

9‐(4‐bromophenyl)‐3,6‐diiodocarbazole

Conditions
ConditionsYield
With potassium iodate; potassium iodide In acetic acid at 80℃; for 4h;98%
With potassium iodate; acetic acid; potassium iodide for 4h; Reflux; Inert atmosphere;85%
With potassium iodate; acetic acid; potassium iodide at 135℃; for 18h;82.22%
N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

3,6-dibromo-9-(4-bromophenyl)-9H-carbazole
73087-83-9

3,6-dibromo-9-(4-bromophenyl)-9H-carbazole

Conditions
ConditionsYield
With N-Bromosuccinimide In dichloromethane at 0℃; for 16h; Schlenk technique; Darkness; Inert atmosphere;98%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 3h;88%
With N-Bromosuccinimide at 0℃; for 8h; Darkness;87%
5-(phenylthio)quinolin-8-amine
56017-36-8

5-(phenylthio)quinolin-8-amine

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

N,N-bis(4-(9H-carbazol-9-yl)phenyl)-5-(phenylthio)quinolin‐8‐amine

N,N-bis(4-(9H-carbazol-9-yl)phenyl)-5-(phenylthio)quinolin‐8‐amine

Conditions
ConditionsYield
With potassium carbonate; nickel dichloride In tetrahydrofuran at 100℃; for 24h; Inert atmosphere;97%
N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole
785051-54-9

9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; palladium diacetate In dimethyl sulfoxide at 80℃; for 8h; Inert atmosphere;96.8%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 85℃; for 48h;87%
Stage #1: N-(4-bromophenyl)carbazole; bis(pinacol)diborane With potassium acetate In dimethyl sulfoxide at 60℃; for 0.25h;
Stage #2: With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In dichloromethane; dimethyl sulfoxide at 80℃; for 6h;
86%
Ethyl bromodifluoroacetate
667-27-6

Ethyl bromodifluoroacetate

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

C22H17F2NO2

C22H17F2NO2

Conditions
ConditionsYield
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; tetrabutylammomium bromide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; zinc In tetrahydrofuran at 60℃; for 24h; Inert atmosphere;96%
8-amino quinoline
578-66-5

8-amino quinoline

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

N,N-bis(4-(9H-carbazol-9-yl)phenyl)quinolin‐8‐amine

N,N-bis(4-(9H-carbazol-9-yl)phenyl)quinolin‐8‐amine

Conditions
ConditionsYield
With sodium hydroxide; nickel dichloride In N,N-dimethyl-formamide at 150℃; for 16h; Reagent/catalyst; Inert atmosphere; Glovebox; Sealed tube; Schlenk technique;96%
With potassium carbonate; nickel dibromide In tetrahydrofuran at 100℃; for 24h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;95%
9,9-diphenyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

9,9-diphenyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

N-(4-(9H-carbazol-9-yl)phenyl)-9,9-diphenyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

N-(4-(9H-carbazol-9-yl)phenyl)-9,9-diphenyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

Conditions
ConditionsYield
With 1,1'-bis(diisopropylphosphino)ferrocene; Pd(dippf)maleimide; sodium t-butanolate In toluene at 120℃; for 24h; Inert atmosphere;95%
N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

N-(4-hydroxyphenyl)carbazole
222620-05-5

N-(4-hydroxyphenyl)carbazole

Conditions
ConditionsYield
With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br2Ni*3H2O; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 36h; Glovebox; Irradiation; Inert atmosphere;95%
With oxygen; triethylamine; sodium iodide In acetonitrile at 32℃; for 24h; Schlenk technique; UV-irradiation;40%
4-phenyl-8-aminoquinoline
55484-55-4

4-phenyl-8-aminoquinoline

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

N,N-bis(4-(9H-carbazol-9-yl)phenyl)-4-phenylquinolin‐8‐amine

N,N-bis(4-(9H-carbazol-9-yl)phenyl)-4-phenylquinolin‐8‐amine

Conditions
ConditionsYield
With nickel dichloride; sodium t-butanolate In water; N,N-dimethyl-formamide at 150℃; for 16h; Inert atmosphere; Glovebox; Sealed tube; Schlenk technique;95%
With nickel(II) sulphate; caesium carbonate In acetonitrile at 100℃; for 24h; Inert atmosphere;86%
N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

C34H36Cl2Si3Zn2

C34H36Cl2Si3Zn2

C70H60N2Si3

C70H60N2Si3

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In toluene at 120℃; for 12h; Inert atmosphere;94%
N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

4,4'-bis(9H-carbazol-9-yl)biphenyl
58328-31-7

4,4'-bis(9H-carbazol-9-yl)biphenyl

Conditions
ConditionsYield
Stage #1: N-(4-bromophenyl)carbazole With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Inert atmosphere;
Stage #2: With copper(l) cyanide In tetrahydrofuran; pentane at -78 - 25℃; Inert atmosphere;
Stage #3: In tetrahydrofuran; pentane at 25℃; for 3h; Inert atmosphere;
93%
Allylchlorodimethylsilane
4028-23-3

Allylchlorodimethylsilane

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

9-(4-(allyldimethylsilyl)phenyl)-9H-carbazole

9-(4-(allyldimethylsilyl)phenyl)-9H-carbazole

Conditions
ConditionsYield
Stage #1: N-(4-bromophenyl)carbazole With n-butyllithium In tetrahydrofuran; acetone at -78℃; for 3h; Inert atmosphere;
Stage #2: Allylchlorodimethylsilane In tetrahydrofuran at 20℃;
93%
6-methoxyquinolin-8-amine
90-52-8

6-methoxyquinolin-8-amine

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

N,N-bis(4-(9H-carbazol-9-yl)phenyl)-6-(methoxy)quinolin‐8‐amine

N,N-bis(4-(9H-carbazol-9-yl)phenyl)-6-(methoxy)quinolin‐8‐amine

Conditions
ConditionsYield
With nickel(II) fluoride; potassium carbonate In tetrahydrofuran at 100℃; for 24h; Inert atmosphere;93%
With nickel dichloride; sodium t-butanolate In water; N,N-dimethyl-formamide at 150℃; for 16h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Glovebox; Sealed tube; Schlenk technique;83%
5-phenylquinoline-8-amine
104711-51-5

5-phenylquinoline-8-amine

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

N,N-bis(4-(9H-carbazol-9-yl)phenyl)-5-(phenyl)quinolin‐8‐amine

N,N-bis(4-(9H-carbazol-9-yl)phenyl)-5-(phenyl)quinolin‐8‐amine

Conditions
ConditionsYield
With nickel dichloride; sodium t-butanolate In water; N,N-dimethyl-formamide at 150℃; for 16h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Glovebox; Sealed tube; Schlenk technique;93%
With nickel(II) fluoride; potassium carbonate In tetrahydrofuran at 100℃; for 24h; Inert atmosphere;91%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

Triisopropyl borate
5419-55-6

Triisopropyl borate

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole
785051-54-9

9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole

Conditions
ConditionsYield
Stage #1: N-(4-bromophenyl)carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Schlenk technique; Inert atmosphere;
Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at -78℃; for 0.166667h; Schlenk technique; Inert atmosphere;
Stage #3: 2,3-dimethyl-2,3-butane diol In tetrahydrofuran; hexane at 20℃; for 69h; Schlenk technique; Inert atmosphere;
93%
Stage #1: N-(4-bromophenyl)carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Schlenk technique; Sealed tube;
Stage #2: Triisopropyl borate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Sealed tube;
Stage #3: 2,3-dimethyl-2,3-butane diol In tetrahydrofuran at 20℃; for 69h; Inert atmosphere; Schlenk technique;
67%
N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

C22H17N3
1432666-69-7

C22H17N3

N,N-bis[3-(pyridin-2-yl)phenyl]4-(9H-carbazole-9-yl)aniline

N,N-bis[3-(pyridin-2-yl)phenyl]4-(9H-carbazole-9-yl)aniline

Conditions
ConditionsYield
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 24h; Buchwald-Hartwig Coupling; Inert atmosphere; Reflux;92%
9,9″-diphenyl-9H,9′H,9″H-3,3':6′,3″-tercarbazole
1060735-19-4

9,9″-diphenyl-9H,9′H,9″H-3,3':6′,3″-tercarbazole

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

C66H42N4

C66H42N4

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 10h; Inert atmosphere; Reflux;92%
N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

p-toluidine
106-49-0

p-toluidine

9-[4-(4-methylphenylamino)phenyl]-9H-carbazole
908139-14-0

9-[4-(4-methylphenylamino)phenyl]-9H-carbazole

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos In toluene at 108℃; for 2h; Inert atmosphere;92%
N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

5-(naphthalen-1-yl)quinolin-8-amine

5-(naphthalen-1-yl)quinolin-8-amine

N,N-bis(4-(9H-carbazol-9-yl)phenyl)-5-(naphthalen-1-yl)quinolin-8-amine

N,N-bis(4-(9H-carbazol-9-yl)phenyl)-5-(naphthalen-1-yl)quinolin-8-amine

Conditions
ConditionsYield
With nickel dichloride; sodium t-butanolate In water; N,N-dimethyl-formamide at 150℃; for 16h; Inert atmosphere; Glovebox; Sealed tube; Schlenk technique;92%
N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

3-chlorophenylboronic acid
63503-60-6

3-chlorophenylboronic acid

C24H16ClN

C24H16ClN

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 12h; Inert atmosphere;92%
N-phenyl-N-[4-(9-phenylcarbazole-3-yl)phenyl]amine
1072194-21-8

N-phenyl-N-[4-(9-phenylcarbazole-3-yl)phenyl]amine

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

4-(9H-carbazol-9-yl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine
1246637-79-5

4-(9H-carbazol-9-yl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine

Conditions
ConditionsYield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In hexane; toluene at 80℃; for 5h; Inert atmosphere;91%
N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

2-phenylaniline
90-41-5

2-phenylaniline

N-(4-(9H-carbazol-9-yl)phenyl)-[1,1'-biphenyl]-2-amine

N-(4-(9H-carbazol-9-yl)phenyl)-[1,1'-biphenyl]-2-amine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 6h; Inert atmosphere; Reflux;91%
N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

4-fluorobenzoyl chloride
403-43-0

4-fluorobenzoyl chloride

(9-(4-bromophenyl)-9H-carbazol-3-yl)(4-fluorophenyl)methanone

(9-(4-bromophenyl)-9H-carbazol-3-yl)(4-fluorophenyl)methanone

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 12h; Friedel-Crafts Acylation;91%

57102-42-8Relevant articles and documents

Design, synthesis and photovoltaic properties of a series of new acceptor-pended conjugated polymers

Wu, Zhihong,Zhu, Yongxiang,Li, Wei,Huang, Yunping,Chen, Junwu,Duan, Chunhui,Huang, Fei,Cao, Yong

, p. 1583 - 1592 (2016)

A series of novel acceptor-pended conjugated polymers featuring a newly developed carbazole-derived unit are designed and synthesized. The relationships between chemical structure and optoelectronic properties of the polymers are systematically investigated. The control of UV-Vis absorption spectra and energy levels in resulting polymers are achieved by introducing suitable pended acceptor units. The photovoltaic properties of the resulting polymers are evaluated by blending the polymers with (6,6)-phenyl-C71-butyric acid methyl ester. The resulting solar cells exhibit moderate performances with high open-circuit voltage. Charge transport properties and morphology were investigated to understand the performance of corresponding solar cells.

A facile approach to prepare a microporous polycarbazole P-tetra(4-(: N -carbazolyl)phenyl)silane network with high CO2 storage and separation properties

Jiang, Fei,Sun, Jianling,Yang, Renqiang,Qiao, Shanlin,An, Zengjian,Huang, Jianqing,Mao, Haifang,Chen, Guie,Ren, Yujie

, p. 4969 - 4973 (2016)

A facile approach is designed to prepare a novel conjugated polycarbazole microporous P-tetra (4-(N-carbazolyl)phenyl)silane (P-TCzPhSi) network with a tetra-substituted silicon center by FeCl3 oxidative coupling polymerization. The adsorption isotherm of N2 reveals that the polymer features a high Brunauer-Emmett-Teller (BET) specific surface area of up to 1856 m2 g-1. The polycarbazole network exhibits good hydrogen (2.5 wt%, 77 K, 1.1 bar), carbon dioxide (23.5 wt%, 273 K, 1.1 bar) and methane (2.5 wt%, 273 K, 1.1 bar) uptake ability.

Light blue and green thermally activated delayed fluorescence from 10H-phenoxaborin-derivatives and their application to organic light-emitting diodes

Kitamoto, Yuichi,Namikawa, Taketo,Ikemizu, Dai,Miyata, Yasuo,Suzuki, Takatsugu,Kita, Hiroshi,Sato, Tetsuo,Oi, Shuichi

, p. 9122 - 9130 (2015)

New luminescent compounds consisting of 10H-phenoxaboryl groups as electron-accepting units and carbazole (9), 9,9-dimethylacridane (10), or phenoxazine (11) as an electron-donating unit have been synthesized. Compounds 10 and 11 showed thermally activated delayed fluorescence (TADF) with light blue and green emissions, respectively, with very high PL quantum yields (PLQYs), however, compound 9 exhibited only a prompt emission and no delayed component. Photoluminescence studies and quantum chemical calculation based on density functional theory (DFT) and time-dependent density functional theory (TD-DFT) revealed that in comparison with compound 9, the HOMO and LUMO for compounds 10 and 11 are well separated, resulting in lowering of ΔEST and effective reverse intersystem crossing (RISC) between a lowest triplet excited state (T1) and a lowest singlet excited state (S1). Organic light-emitting diodes (OLEDs) using compounds 10 and 11 exhibited light blue and green emissions with very good maximum ηext of 15.1% and 22.1%, respectively.

Synthesis and photoluminescent properties of series ternary lanthanide (Eu(III), Sm(III), Nd(III), Er(III), Yb(III)) complexes containing 4,4,4-trifluoro-1-(2-naphthyl)-1,3-butanedionate and carbazole-functionalized ligand

Wu, Jing,Li, Hong-Yan,Xu, Qiu-Lei,Zhu, Yu-Cheng,Tao, Yun-Mei,Li, Huan-Rong,Zheng, You-Xuan,Zuo, Jing-Lin,You, Xiao-Zeng

, p. 2394 - 2400 (2010)

A series of new ternary lanthanide complexes Ln(TFNB)3L (where Ln = Eu, Sm, Nd, Er, Yb, TFNB = 4,4,4-trifluoro-1-(2-naphthyl)-1,3- butanedionate, L = 1-(4-carbazolylphenyl)-2-pyridinyl benzimidazole) have been synthesised. The photoluminescence properties and TGA of them are described in detail. The trifluorinated ligand TFNB displays excellent antenna effect to sensitize the Ln(III) ions to emit characteristic spectra. The carbazole-containing ligand L is testified to be an outstanding synergistic ligand. The luminescence properties investigated and the quantum efficiency measured in dichloromethane solution of Eu(TFNB)3L and Sm(TFNB) 3L show that the carbazole moiety is good at absorbing energy to sensitize the metal-centered emitting states and can make the complexes more rigid, provide efficient shielding of the Ln(III) core towards external quenching compared with the reference complexes of Eu(TFNB)3(Pybm) and Sm(TFNB)3(Pybm) (Pybm = 2-(2-pyridine)-benzimidazole) which have no carbazole unit. The quantum efficiency of Eu(TFNB)3L in air-equilibrated CH2Cl2 solution is calculated to be 14.8% by using air-equilibrated aqueous [Ru(bpy)3]2+· 2Cl- solution as reference sample (Φstd = 2.8%).

Communication of Bichromophore Emission upon Aggregation – Aroyl-S,N-ketene Acetals as Multifunctional Sensor Merocyanines

Biesen, Lukas,May, Lars,Nirmalananthan-Budau, Nithiya,Hoffmann, Katrin,Resch-Genger, Ute,Müller, Thomas J. J.

supporting information, p. 13426 - 13434 (2021/08/06)

Aroyl-S,N-ketene acetal-based bichromophores can be readily synthesized in a consecutive three-component synthesis in good to excellent yields by condensation of aroyl chlorides and an N-(p-bromobenzyl) 2-methyl benzothiazolium salt followed by a Suzuki coupling, yielding a library of 31 bichromophoric fluorophores with substitution pattern-tunable emission properties. Varying both chromophores enables different communication pathways between the chromophores, exploiting aggregation-induced emission (AIE) and energy transfer (ET) properties, and thus, furnishing aggregation-based fluorescence switches. Possible applications range from fluorometric analysis of alcoholic beverages to pH sensors.

Molecular Engineering through Control of Structural Deformation for Highly Efficient Ultralong Organic Phosphorescence

Yin, Zheng,Gu, Mingxing,Ma, Huili,Jiang, Xueyan,Zhi, Jiahuan,Wang, Yafei,Yang, Huifang,Zhu, Weiguo,An, Zhongfu

supporting information, p. 2058 - 2063 (2020/11/30)

It is an enormous challenge to achieve highly efficient organic room-temperature phosphorescence (RTP) with a long lifetime. We demonstrate that, by bridging the carbazole and halogenated phenyl ring with a methylene linker, RTP phosphors CzBX (X=Cl, Br) present high phosphorescence efficiency (ΦPh). A ΦPh up to 38 % was obtained for CzBBr with a lifetime of 220 ms, which is much higher than that of compounds CzPX (X=Cl, Br) with a C?N bond as a linker (ΦPh3 methylene linkers restrain the nonradiative decay channel, leading to the high phosphorescence efficiency in CzBBr. This research paves a new road toward highly efficient and long-lived RTP materials with potential applications in anti-counterfeiting or data encryption.

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