N-phenyl-9H-carbazol-3-boronic acid
1,4-bromoiodobenzene
3-(4-bromophenyl)-9-phenyl-9H carbazole
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
1.4-dibromobenzene
3-(4-bromophenyl)-9-phenyl-9H carbazole
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
9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-9H-carbazole
3-(4-bromophenyl)-9-phenyl-9H carbazole
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
1,4-bromoiodobenzene
3-(4-bromophenyl)-9-phenyl-9H carbazole
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
3-iodo-9-phenyl-9H-carbazole
3-(4-bromophenyl)-9-phenyl-9H carbazole
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
1,4-bromoiodobenzene
A
3-(4-bromophenyl)-9-phenyl-9H carbazole
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
3-(4-bromophenyl)-9-phenyl-9H carbazole
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
3-(4-bromophenyl)-9-phenyl-9H carbazole
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
3-(4-bromophenyl)-9-phenyl-9H carbazole
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
1.4-dibromobenzene
3-(4-bromophenyl)-9-phenyl-9H carbazole
Conditions | Yield |
---|---|
With potassium carbonate; palladium In toluene at 80℃; for 12h; Inert atmosphere; |
5-bromo-2-nitro-biphenyl
3-(4-bromophenyl)-9-phenyl-9H carbazole
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
3-(4-bromophenyl)-9-phenyl-9H carbazole
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
3-(4-bromophenyl)-9-phenyl-9H carbazole
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
3-(4-bromophenyl)-9-phenyl-9H carbazole
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
3-(4-bromophenyl)-9-phenyl-9H carbazole
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
3-(4-bromophenyl)-9-phenyl-9H carbazole
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
3-(4-bromophenyl)-9-phenyl-9H carbazole
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 |
3-(4-bromophenyl)-9-phenyl-9H carbazole
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 |
3-(4-bromophenyl)-9-phenyl-9H carbazole
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
3-(4-bromophenyl)-9-phenyl-9H carbazole
Conditions | Yield |
---|---|
With copper; potassium carbonate; sodium sulfate In nitrobenzene at 200℃; |
3-(4-bromophenyl)-9-phenyl-9H carbazole
bis(pinacol)diborane
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
3-(4-bromophenyl)-9-phenyl-9H carbazole
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
4-Aminobiphenyl
N‐[4‐(9‐phenyl‐9H‐carbazol‐3‐yl)phenyl]‐[1,1'‐biphenyl]‐4‐amine
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
3-(4-bromophenyl)-9-phenyl-9H carbazole
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
3-(4-bromophenyl)-9-phenyl-9H carbazole
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
Conditions | Yield |
---|---|
With 1,1'-bis(diisopropylphosphino)ferrocene; Pd(dippf)maleimide; sodium t-butanolate In toluene at 70℃; for 24h; Inert atmosphere; | 93% |
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
2-aminofluorene
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
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
3-(4-bromophenyl)-9-phenyl-9H carbazole
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
4-(9-phenyl-9H-carbazol-3-yl)phenylboronic acid
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
3-(4-bromophenyl)-9-phenyl-9H carbazole
4-(9-phenyl-9H-carbazol-3-yl)phenylboronic acid
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
3-(4-bromophenyl)-9-phenyl-9H carbazole
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
3-(4-bromophenyl)-9-phenyl-9H carbazole
water
4-(9-phenyl-9H-carbazol-3-yl)phenylboronic acid
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
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
1-Naphthylboronic acid
3-[4-(naphthalen-1-yl)phenyl]-9-phenyl-9H-carbazole
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% |
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
3-(4-bromophenyl)-9-phenyl-9H carbazole
N-(1,1‘-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine
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% |
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
N-phenyl-1,2-benzenediamine
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
3-chlorophenylboronic acid
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
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% |
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
3-(4-bromophenyl)-9-phenyl-9H carbazole
(4-(1-naphthyl)-phenyl)-(4-(9-phenyl-9H-carbazol-3-yl)-phenyl)-phenyl-amine
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
3,6-di(benzothiophen-4-yl)-9H-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
1-(4'-aminophenyl)naphthalene
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% |
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% |
The 3-(4-Bromophenyl)-9-phenyl-9H-Carbazole, with the CAS registry number 1028647-93-9, has the molecular formula C24H16BrN. In addition, its molecular weight is 398.2945. Its systematic name is called 3-(4-bromophenyl)-9-phenyl-carbazole.
Physical properties of 3-(4-Bromophenyl)-9-phenyl-9H-Carbazole: (1)ACD/LogP: 8.22; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 8.218; (4)ACD/LogD (pH 7.4): 8.218; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 1000000; (7)ACD/KOC (pH 5.5): 703901.313; (8)ACD/KOC (pH 7.4): 703901.313; (9)#H bond acceptors: 1; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.67; (12)Molar Refractivity: 111.922 cm3; (13)Molar Volume: 299.596 cm3; (14)Surface Tension: 47.057 dyne/cm; (15)Density: 1.329 g/cm3; (16)Flash Point: 292.791 °C; (17)Enthalpy of Vaporization: 84.312 kJ/mol; (18)Boiling Point: 560.518 °C at 760 mmHg; (19)Vapour Pressure: 0 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: c1ccc(cc1)n2c3ccccc3c4c2ccc(c4)c5ccc(cc5)Br
(2)InChI: InChI=1/C24H16BrN/c25-19-13-10-17(11-14-19)18-12-15-24-22(16-18)21-8-4-5-9-23(21)26(24)20-6-2-1-3-7-20/h1-16H
(3)InChIKey: JEYLGFCAZBGCMC-UHFFFAOYAI
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