1028647-93-9

Basic information

• Product Name: 3-(4-bromophenyl)-N-phenylcarbazole
• Synonyms: 3-(4-bromophenyl)-N-phenylcarbazole;3-(4-Bromophenyl)-9-phenyl-9H-carbazole;3-(4-broMophenyl)-9-phenyl Carbazole;N-phenyl-3-(4-broMophenyl)carbazole;3-(4-broMophenyl)-9-phenyl-9H-carbazole 003;3-(4-BroMophenyl)-9-phenyl-9H-carbazole,3-93-(4-broMophenyl)-N-phenylcarbazole;3-(4-broMophenyl)-N-phenyl-9H-Carbazole;3-(4-broMophenyl)-9-phenyl-9H-carbazole (BPPC)
• CAS NO: 1028647-93-9
• Molecular Formula: C₂₄H₁₆BrN
• Molecular Weight: 398.29454
• EINECS: 1312995-182-4
• Product Categories: organic chemicals and derivatives/others;OLED;OLED materials,pharm chemical,electronic;intermediate
• Mol File: 1028647-93-9.mol
• Article Data: 59

Chemical Properties

• Melting Point: 136.0 to 140.0 °C
• Boiling Point: 560.518 °C at 760 mmHg
• Flash Point: 292.791 °C
• Appearance: /Solid
• Density: 1.32
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: slightly sol. in Toluene
• CAS DataBase Reference: 3-(4-bromophenyl)-N-phenylcarbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-bromophenyl)-N-phenylcarbazole(1028647-93-9)
• EPA Substance Registry System: 3-(4-bromophenyl)-N-phenylcarbazole(1028647-93-9)

Safety Data

• Hazardous Substances Data: 1028647-93-9(Hazardous Substances Data)

Usage

Uses

3-(4-BROMOPHENYL)-9-PHENYL-9H-CARBAZOLE is a useful research chemical.

Chemical Properties

White crystalline powder

Synthetic route

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 1,4-bromoiodobenzene (589-87-7) → 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 60℃; for 3h;	92%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 90℃; for 8h; Inert atmosphere;	88%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 24h; Reflux;	78%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 1.4-dibromobenzene (106-37-6) → 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene; sodium t-butanolate In toluene at 110℃; for 8h; Inert atmosphere;	85.6%

1,4-bromoiodobenzene (589-87-7) + 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-9H-carbazole (1126522-69-7) → 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 12h; Inert atmosphere; Reflux;	81%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 12h; Inert atmosphere; Reflux;	81%
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In tetrahydrofuran; water at 80℃; Suzuki Coupling;	77%

3-bromo-9-phenyl-9H-carbazole (1153-85-1) + 1,4-bromoiodobenzene (589-87-7) → 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9)

Conditions	Yield
Stage #1: 1,4-bromoiodobenzene With iodine; magnesium In tetrahydrofuran for 2h; Inert atmosphere; Reflux; Stage #2: 3-bromo-9-phenyl-9H-carbazole at 50 - 85℃; for 16h; Inert atmosphere;	77.4%
Stage #1: 3-bromo-9-phenyl-9H-carbazole With iodine; magnesium In tetrahydrofuran for 1h; Inert atmosphere; Reflux; Stage #2: 1,4-bromoiodobenzene at 50 - 85℃; for 16h; Inert atmosphere;	75.3%

4-Bromophenylboronic acid (5467-74-3) + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 65℃; for 7h;	76%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 65℃; for 7h;	76%
With potassium carbonate; palladium diacetate; tris-(o-tolyl)phosphine In 1,2-dimethoxyethane; water at 80℃; for 9.5h; Suzuki Coupling;	49%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 1,4-bromoiodobenzene (589-87-7) → 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) + 1,4-bis(9-phenyl-9H-carbazol-3-yl)benzene

Conditions	Yield
With potassium carbonate; palladium diacetate; tris-(o-tolyl)phosphine In ethanol; water; toluene at 80℃; for 6h; Suzuki-Miyaura Coupling; Inert atmosphere;	A 75% B n/a
With potassium carbonate; palladium diacetate; tris-(o-tolyl)phosphine In ethanol; water; toluene at 80℃; for 6h; Inert atmosphere;

3-iodo-9-phenyl-9H-carbazole (502161-03-7) → 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / toluene; hexane; diethyl ether / 1 h / -45 - -5 °C / Inert atmosphere 1.2: 2 h / -45 °C 1.3: 20 °C 2.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; water / 10 h / Reflux; Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / toluene; hexane; diethyl ether / 1 h / -45 - -5 °C / Inert atmosphere 1.2: 2 h / -45 °C / Inert atmosphere 1.3: 20 °C / Inert atmosphere 2.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; water / 10 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / toluene; hexane / 1 h / -45 - -5 °C / Inert atmosphere 1.2: 2 h / -45 °C 1.3: 20 °C 2.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; water / 10 h / Inert atmosphere; Reflux View Scheme

N-phenylcarbazole (1150-62-5) → 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium iodide; sulfuric acid; potassium iodate / ethanol / 2 h / 75 °C 2.1: n-butyllithium / toluene; hexane; diethyl ether / 1 h / -45 - -5 °C / Inert atmosphere 2.2: 2 h / -45 °C 2.3: 20 °C 3.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; water / 10 h / Reflux; Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: potassium iodide; sulfuric acid; potassium iodate / ethanol / 2 h / 75 °C 2.1: n-butyllithium / toluene; hexane; diethyl ether / 1 h / -45 - -5 °C / Inert atmosphere 2.2: 2 h / -45 °C / Inert atmosphere 2.3: 20 °C / Inert atmosphere 3.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; water / 10 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 3 steps 1.1: potassium iodide; sulfuric acid; potassium iodate / ethanol / 2 h / 75 °C 2.1: n-butyllithium / toluene; hexane / 1 h / -45 - -5 °C / Inert atmosphere 2.2: 2 h / -45 °C 2.3: 20 °C 3.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; water / 10 h / Inert atmosphere; Reflux View Scheme

3-bromo-9-phenyl-9H-carbazole (1153-85-1) → 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -73 °C / Inert atmosphere 1.2: 4 h / Inert atmosphere 2.1: potassium phosphate; triphenylphosphine; palladium diacetate / toluene; ethanol; water / 2 h / 75 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 24 h 2: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / Reflux View Scheme
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 24 h 2: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / Reflux View Scheme

3-bromo-9-phenyl-9H-carbazole (1153-85-1) + 1.4-dibromobenzene (106-37-6) → 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9)

Conditions	Yield
With potassium carbonate; palladium In toluene at 80℃; for 12h; Inert atmosphere;

5-bromo-2-nitro-biphenyl (105971-15-1) → 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 2.1: potassium carbonate; sodium sulfate; copper / nitrobenzene / 200 °C 3.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C 3.2: 12 h / -78 - 20 °C 4.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Reflux View Scheme
Multi-step reaction with 4 steps 1.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 2.1: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux 3.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 3.2: 12 h / -78 - 20 °C / Inert atmosphere 4.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 4 steps 1.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 2.1: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux 3.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 3.2: 12 h / -78 - 20 °C / Inert atmosphere 4.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 24 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 4 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 90 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 80 °C 3: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 4: sodium sulfate; copper; potassium carbonate / nitrobenzene / 200 °C View Scheme

3-bromo-9H-carbazole (1592-95-6) → 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate; sodium sulfate; copper / nitrobenzene / 200 °C 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C 2.2: 12 h / -78 - 20 °C 3.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 2.2: 12 h / -78 - 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 3 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate / toluene / 24 h / 100 °C 2.1: n-butyllithium / hexane; diethyl ether / 0.5 h / -78 °C 2.2: -78 °C 2.3: 20 °C 3.1: sodium hydroxide; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 80 - 90 °C View Scheme
Multi-step reaction with 3 steps 1.1: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 2.2: 12 h / -78 - 20 °C / Inert atmosphere 3.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 24 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 3 steps 1: sodium sulfate; potassium carbonate; copper / nitrobenzene / 195 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 90 °C 3: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 80 °C View Scheme

phenylboronic acid (98-80-6) → 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 24 h / 80 °C 2.1: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3.1: potassium carbonate; sodium sulfate; copper / nitrobenzene / 200 °C 4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C 4.2: 12 h / -78 - 20 °C 5.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Reflux View Scheme
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / Inert atmosphere; Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3.1: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux 4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 4.2: 12 h / -78 - 20 °C / Inert atmosphere 5.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 5 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3.1: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux 4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 4.2: 12 h / -78 - 20 °C / Inert atmosphere 5.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 24 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 5 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 80 °C 2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 90 °C 3: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 80 °C 4: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 5: sodium sulfate; copper; potassium carbonate / nitrobenzene / 200 °C View Scheme

2-iodo-1-nitro-4-bromobenzene (343864-78-8) → 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 24 h / 80 °C 2.1: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3.1: potassium carbonate; sodium sulfate; copper / nitrobenzene / 200 °C 4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C 4.2: 12 h / -78 - 20 °C 5.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Reflux View Scheme
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / Inert atmosphere; Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3.1: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux 4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 4.2: 12 h / -78 - 20 °C / Inert atmosphere 5.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 5 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 2.1: triphenylphosphine / 1,2-dichloro-benzene / Inert atmosphere; Reflux 3.1: potassium carbonate; copper / nitrobenzene / 16 h / Inert atmosphere; Reflux 4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 4.2: 12 h / -78 - 20 °C / Inert atmosphere 5.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 24 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 5 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 80 °C 2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 90 °C 3: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 80 °C 4: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 5: sodium sulfate; copper; potassium carbonate / nitrobenzene / 200 °C View Scheme

iodobenzene (591-50-4) → 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate / toluene / 24 h / 100 °C 2.1: n-butyllithium / hexane; diethyl ether / 0.5 h / -78 °C 2.2: -78 °C 2.3: 20 °C 3.1: sodium hydroxide; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 80 - 90 °C View Scheme
Multi-step reaction with 3 steps 1: sodium sulfate; potassium carbonate; copper / nitrobenzene / 195 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 90 °C 3: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / 80 °C View Scheme

9H-carbazole (86-74-8) → 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 24 h / 140 °C 2.1: iodine; sulfuric acid / water; methanol / 20 h 3.1: magnesium / tetrahydrofuran / 12 h / 75 - 80 °C 3.2: 5 h / 0 °C 3.3: 2 h / 20 °C / Cooling 4.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; toluene / 12 h / Reflux View Scheme
Multi-step reaction with 4 steps 1.1: potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 24 h / 140 °C 2.1: iodine; sulfuric acid / methanol; water / 20 h / 5 °C / Cooling 3.1: magnesium; water / tetrahydrofuran / 12 h / 75 - 80 °C 3.2: 5 h / -20 - 0 °C 3.3: 2 h / 0 - 20 °C 4.1: potassium carbonate; triethylamine; tetrakis(triphenylphosphine) palladium(0) / toluene; water / 12 h / Reflux View Scheme
Multi-step reaction with 4 steps 1: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine / toluene / 24 h / 100 °C 2: N-Bromosuccinimide / dichloromethane / 24 h / 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 24 h 4: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / Reflux View Scheme

bromobenzene (108-86-1) → 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 24 h / 140 °C 2.1: iodine; sulfuric acid / water; methanol / 20 h 3.1: magnesium / tetrahydrofuran / 12 h / 75 - 80 °C 3.2: 5 h / 0 °C 3.3: 2 h / 20 °C / Cooling 4.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; toluene / 12 h / Reflux View Scheme
Multi-step reaction with 4 steps 1.1: potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 24 h / 140 °C 2.1: iodine; sulfuric acid / methanol; water / 20 h / 5 °C / Cooling 3.1: magnesium; water / tetrahydrofuran / 12 h / 75 - 80 °C 3.2: 5 h / -20 - 0 °C 3.3: 2 h / 0 - 20 °C 4.1: potassium carbonate; triethylamine; tetrakis(triphenylphosphine) palladium(0) / toluene; water / 12 h / Reflux View Scheme
Multi-step reaction with 4 steps 1: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine / toluene / 24 h / 100 °C 2: N-Bromosuccinimide / dichloromethane / 24 h / 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 24 h 4: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / Reflux View Scheme

C18H20BNO4 → 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 3: sodium sulfate; copper; potassium carbonate / nitrobenzene / 200 °C View Scheme

C18H12BrNO2 → 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: triphenylphosphine / 1,2-dichloro-benzene / 200 °C 2: sodium sulfate; copper; potassium carbonate / nitrobenzene / 200 °C View Scheme

iodobenzene (591-50-4) + 3-(4-bromophenyl)-9H-carbazole → 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9)

Conditions	Yield
With copper; potassium carbonate; sodium sulfate In nitrobenzene at 200℃;

3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) + bis(pinacol)diborane (73183-34-3) → 9-phenyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 100℃; for 12h; Inert atmosphere;	99%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide for 8h; Inert atmosphere; Reflux;	91%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 80℃; for 8h; Inert atmosphere;	91%

dibenzothiophen-2-ylamine (7428-91-3) + 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) → N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)dibenzo[b,d]thiophen-2-amine

Conditions	Yield
With 1,1'-bis(diisopropylphosphino)ferrocene; Pd(dippf)maleimide; sodium t-butanolate In toluene at 70℃; for 20h; Inert atmosphere;	96%

3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) + 4-Aminobiphenyl (92-67-1) → N‐[4‐(9‐phenyl‐9H‐carbazol‐3‐yl)phenyl]‐[1,1'‐biphenyl]‐4‐amine (1160294-96-1)

Conditions	Yield
With 1,1'-bis(diisopropylphosphino)ferrocene; Pd(dippf)maleimide; sodium t-butanolate In toluene at 70℃; for 20h; Inert atmosphere;	95%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium tert-butylate In toluene at 85℃; for 2h;	83%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium tert-butylate In toluene at 85℃; for 1h;	80%

9-ethyl-9H-carbazol-3-ylamine (132-32-1) + 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) → 9-ethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-carbazol-3-amine

Conditions	Yield
With 1,1'-bis(diisopropylphosphino)ferrocene; Pd(dippf)maleimide; sodium t-butanolate In toluene at 70℃; for 20h; Inert atmosphere;	95%

9,9-dimethyl-9H-fluoren-2-ylamine (108714-73-4) + 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) → 9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

Conditions	Yield
With 1,1'-bis(diisopropylphosphino)ferrocene; Pd(dippf)maleimide; sodium t-butanolate In toluene at 70℃; for 20h; Catalytic behavior; Inert atmosphere;	94%
With 1,1'-bis(diisopropylphosphino)ferrocene; [Pd(dippf)(maleimide)]; sodium t-butanolate In toluene at 70℃; for 20h; Inert atmosphere; Sealed tube; Schlenk technique;	94%
With 1,1'-bis(diisopropylphosphino)ferrocene; 1,1′-bis(diisopropylphosphino)ferrocene palladium(0)-maleimide; sodium t-butanolate In toluene at 70℃; for 20h; Temperature; Buchwald-Hartwig Coupling; Schlenk technique; Sealed tube; Inert atmosphere;	94%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 100℃; for 5h;	85%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 90℃; for 6h; Inert atmosphere;	74%

3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) + 9,9-diphenyl-9H-fluoren-2-ylamine → 9,9-diphenyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

Conditions	Yield
With 1,1'-bis(diisopropylphosphino)ferrocene; Pd(dippf)maleimide; sodium t-butanolate In toluene at 70℃; for 24h; Inert atmosphere;	93%

phenoxazine (135-67-1) + 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) → C36H24N2O

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene for 12h; Inert atmosphere; Reflux;	92%
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene for 12h; Inert atmosphere; Reflux;	92%

3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) + 2-aminofluorene (153-78-6) → N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

Conditions	Yield
With 1,1'-bis(diisopropylphosphino)ferrocene; Pd(dippf)maleimide; sodium t-butanolate In toluene at 70℃; for 20h; Inert atmosphere;	92%

3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) → C24H15BrIN

Conditions	Yield
Stage #1: 3-(4-bromophenyl)-9-phenyl-9H-carbazole With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h; Stage #2: With iodine In tetrahydrofuran at 0 - 20℃; for 20h;	90%

8-amino quinoline (578-66-5) + 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) → N,N-bis(4-(9-phenyl-9H-carbazol-3-yl)phenyl)quinolin-8-amine

Conditions	Yield
With sodium hydroxide; nickel dichloride In N,N-dimethyl-formamide at 150℃; for 16h; Inert atmosphere; Glovebox; Sealed tube; Schlenk technique;	90%

3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) → 4-(9-phenyl-9H-carbazol-3-yl)phenylboronic acid (1240963-55-6)

Conditions	Yield
Stage #1: 3-(4-bromophenyl)-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 20h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water for 7h;	88%

Trimethyl borate (121-43-7) + 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) → 4-(9-phenyl-9H-carbazol-3-yl)phenylboronic acid (1240963-55-6)

Conditions	Yield
Stage #1: Trimethyl borate; 3-(4-bromophenyl)-9-phenyl-9H-carbazole In tetrahydrofuran at -78 - 20℃; for 20h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water for 7h;	88%
Stage #1: 3-(4-bromophenyl)-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 20h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water for 7h; Inert atmosphere;	88%

dibenzo[b,d]furan-2-amine (3693-22-9) + 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) → N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)dibenzo[b,d]furan-2-amine

Conditions	Yield
With 1,1'-bis(diisopropylphosphino)ferrocene; Pd(dippf)maleimide; sodium t-butanolate In toluene at 70℃; for 20h; Inert atmosphere;	88%

Trimethyl borate (121-43-7) + 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) + water (7732-18-5) → 4-(9-phenyl-9H-carbazol-3-yl)phenylboronic acid (1240963-55-6)

Conditions	Yield
Stage #1: 3-(4-bromophenyl)-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 14h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 20h; Stage #3: water With hydrogenchloride In tetrahydrofuran; hexane for 7h;	88%
Stage #1: 3-(4-bromophenyl)-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: Trimethyl borate at -78℃; Inert atmosphere; Stage #3: water With hydrogenchloride for 0.5h; Inert atmosphere;	83.1%

3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) + 9-(naphthalen-2-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole → C46H30N2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 120℃; for 4h;	87%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 120℃; for 4h;	37%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 120℃; for 4h;	37%

3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) + 1-Naphthylboronic acid (13922-41-3) → 3-[4-(naphthalen-1-yl)phenyl]-9-phenyl-9H-carbazole (1365452-27-2)

Conditions	Yield
With potassium carbonate; palladium diacetate; tris-(o-tolyl)phosphine In ethanol; water; toluene at 90℃; for 14h; Suzuki-Miyaura reaction; Inert atmosphere;	86%

3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) + C46H55NO4 → C70H70N2O4

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene; hexane at 100℃; for 8h; Inert atmosphere;	86%

N‑(biphenyl‑4‑yl)‑9,9‑dimethyl‑9H‑fluorene‑2‑amine (897671-69-1) + 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) → N-(1,1‘-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (1242056-42-3)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate In toluene at 100℃; for 24h;	85%
With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate In toluene at 100℃; for 24h;	85%
With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate In toluene at 100℃; for 24h;	85%

3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) + C34H23N3 → C58H38N4

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene; toluene at 145℃;	84%

3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) + N-phenyl-1,2-benzenediamine (534-85-0) → N1-phenyl-N2-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)benzene-1,2-diamine

Conditions	Yield
With 1,1'-bis(diisopropylphosphino)ferrocene; Pd(dippf)maleimide; sodium t-butanolate In toluene at 70℃; for 20h; Inert atmosphere;	84%

3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) + 3-chlorophenylboronic acid (63503-60-6) → 3-(3'-chloro-1,1'-biphenyl-4-yl)-9-phenyl-9H-carbazole

Conditions	Yield
With palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine In ethanol; water; toluene at 60 - 80℃; for 12h; Inert atmosphere;	84%

3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) + 5,8-dihydro-5-phenyl-5,8-diazaindeno[2,1-c]fluorene → C48H31N3

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene for 16h; Reflux; Inert atmosphere;	83%
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 12h; Inert atmosphere; Reflux;	77%
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene; toluene for 12h; Reflux; Inert atmosphere;	77%

3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) + C38H27N → C62H42N2

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 100℃; Buchwald-Hartwig Coupling;	83%

N-[4-(1-naphthalenyl)phenyl]-phenyl-4-amine (897671-78-2) + 3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) → (4-(1-naphthyl)-phenyl)-(4-(9-phenyl-9H-carbazol-3-yl)-phenyl)-phenyl-amine (1160294-63-2)

Conditions	Yield
With sodium t-butanolate; tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0) In hexane; xylene at 120℃; for 4.5h; Product distribution / selectivity; Buchwald-Hartwig reaction;	82%

3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) + 3,6-di(benzothiophen-4-yl)-9H-carbazole (1365891-56-0) → 9-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-3,6-di(benzothiophen-4-yl)carbazole

Conditions	Yield
With potassium phosphate; copper(l) iodide; (1R,2R)-1,2-diaminocyclohexane In 1,4-dioxane for 24h; Reflux;	82%

3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) + 1-(4'-aminophenyl)naphthalene (125404-00-4) → 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)diphenylamine

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In hexane; toluene at 80 - 110℃; for 8h; Inert atmosphere;	80%
With sodium t-butanolate; tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0) In hexane; toluene at 60 - 80℃; for 3h; Hartwig-Buchwald reaction; Inert atmosphere;	63%

3-(4-bromophenyl)-9-phenyl-9H carbazole (1028647-93-9) + C34H23N3 → C58H38N4

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene; toluene at 145℃;	80%

Upstream product

• 854952-58-2 N-phenyl-9H-carbazol-3-boronic acid 
• 106-37-6 1.4-dibromobenzene 
• 591-50-4 iodobenzene 
• 108-86-1 bromobenzene 
• 86-74-8 9H-carbazole 
• 1153-85-1 3-bromo-9-phenyl-9H-carbazole 
• 589-87-7 1,4-bromoiodobenzene 
• 343864-78-8 4-bromo-2-iodo-1-nitrobenzene 
• 98-80-6 phenylboronic acid 
• 1592-95-6 3-bromo-9H-carbazole 
• 105971-15-1 5-bromo-2-nitro-biphenyl 
• 1126522-69-7 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-9H-carbazole 
• 1150-62-5 N-phenylcarbazole 
• 502161-03-7 3-iodo-9-phenyl-9H-carbazole 

Downstream Products

• 1160294-63-2 (4-(1-naphthyl)-phenyl)-(4-(9-phenyl-9H-carbazol-3-yl)-phenyl)-phenyl-amine 
• 1160294-62-1 (biphenyl-4-yl)(phenyl)[4'-(9-phenyl-9H-carbazol-3-yl)biphenyl-4-yl]amine 
• 1028648-66-9 bis(biphenyl-4-yl)[4'-(9-phenyl-9H-carbazol-3-yl)biphenyl-4-yl]amine 
• 1222863-20-8 4-[4-(1-naphthyl)phenyl]-4'-(9-phenyl-9H-carbazol-3-yl)diphenylamine 
• 1160294-58-5 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine 
• 1240963-55-6 4-(9-phenyl-9H-carbazol-3-yl)phenylboronic acid 
• 1365452-27-2 3-[4-(naphthalen-1-yl)phenyl]-9-phenyl-9H-carbazole 
• 1369431-19-5 3-[4-(9-phenanthryl)-phenyl]-9-phenyl-9H-carbazole 
• 1369431-21-9 9-phenyl-3-[4-(triphenylen-2-yl)-phenyl]-9H-carbazole 
• 1369431-33-3 9-phenyl-9H-3-{4-[3,5-di(phenanthren-9-yl)phenyl]phenyl}carbazole 
• 1160294-96-1 N‐[4‐(9‐phenyl‐9H‐carbazol‐3‐yl)phenyl]‐[1,1'‐biphenyl]‐4‐amine 
• 1026033-83-9 N,N'-diphenyl-N,N'-bis(4-(9-phenylcarbazolyl)phenyl)-1,4-diaminobenzene 

Relevant articles and documents

Tertiary amine derivatives and organic electroluminescent device including the same

A UV-region high-energy external light source is effectively absorbed to minimize damage to organic materials in the organic electroluminescent device. 1 Is a cross-sectional view of an organic electroluminescence device according to the present invention. O-2 electrode 1 Or more organic material layers disposed between the (2) and (1) th electrodes. A capping layer is included. The organic material layer and/or the capping layer may include the 1 st amine derivative represented by Formula 3. Chemical Formula 1. Wherein each substituent in Formula 1 is as defined in the description of the invention.

Boron-nitrogen heteropolyaromatic ring compound and application thereof

The invention relates to the technical field of display, in particular to a boron-nitrogen heteropolyaromatic ring compound and application thereof. The boron-nitrogen heteropolyaromatic ring compoundhas a structure as shown in a formula I, the compound is based on interaction between a boron-nitrogen structural unit and a surrounding aromatic ring or heteroaromatic ring. The boron-nitrogen heteropolyaromatic ring compound has higher glass transition temperature, higher and balanced charge mobility and more suitable single-triplet state energy, and when the boron-nitrogen heteropolyaromatic ring compound is used as a light-emitting main body material of an organic light-emitting device, the light-emitting efficiency of the device can be greatly improved, and the working voltage of the device is effectively reduced.

Organic compound, and organic electroluminescent device and display device comprising organic compound (by machine translation)

The embodiment of the invention provides an organic compound with the following formula (I) and an organic electroluminescent device and a display device comprising the organic compound. The organic compound provided by the embodiment of the invention has higher refractive index and lower evaporation temperature; the light extraction efficiency of the organic electroluminescent device can be improved as the light extraction layer material; and the service life of the device can be prolonged. (by machine translation)