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

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

Used in Research and Development:
3-(4-bromophenyl)-N-phenylcarbazole is used as a research chemical for the development of new compounds and materials. Its unique structure and properties make it a promising candidate for various applications in the fields of chemistry and materials science.
Used in Organic Synthesis:
In the field of organic synthesis, 3-(4-bromophenyl)-N-phenylcarbazole is used as a building block or intermediate for the synthesis of more complex organic molecules. Its reactivity and functional groups can be exploited to create a wide range of compounds with potential applications in various industries.
Used in Pharmaceutical Research:
3-(4-bromophenyl)-N-phenylcarbazole is also used in pharmaceutical research as a potential lead compound for the development of new drugs. Its unique structure and properties may offer novel therapeutic opportunities, and further research is needed to explore its potential in this area.
Used in Material Science:
In material science, 3-(4-bromophenyl)-N-phenylcarbazole can be used as a component in the development of new materials with specific properties. Its incorporation into polymers, for example, may result in materials with improved stability, conductivity, or other desirable characteristics.
Overall, 3-(4-bromophenyl)-N-phenylcarbazole is a versatile research chemical with potential applications in various fields, including organic synthesis, pharmaceutical research, and material science. Its unique structure and properties make it a valuable tool for scientists and researchers working to develop new compounds and materials with innovative properties and applications.

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

• 1153-85-1 3-bromo-9-phenyl-9H-carbazole 
• 589-87-7 1,4-bromoiodobenzene 
• 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 
• 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 
• 1160294-96-1 N‐[4‐(9‐phenyl‐9H‐carbazol‐3‐yl)phenyl]‐[1,1'‐biphenyl]‐4‐amine 
• 1240963-55-6 4-(9-phenyl-9H-carbazol-3-yl)phenylboronic acid 
• 1026033-83-9 N,N'-diphenyl-N,N'-bis(4-(9-phenylcarbazolyl)phenyl)-1,4-diaminobenzene 
• 1072194-21-8 N-phenyl-N-[4-(9-phenylcarbazole-3-yl)phenyl]amine 

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