1060735-14-9

Basic information

• Product Name: 9-Phenyl-9H,9'H-[3,3']bicarbazolyl
• Synonyms: 9-Phenyl-9H,9'H-[3,3']bicarbazolyl;3-(9-Phenyl-9H-carbazol-3-yl)-9H-carbazole;9-phenyl-9H,9'H-3,3'-bicarbazole;3-(9-phenyl-carbazol-3-yl)-9H-carbazole;N-Phenyl-3,3'-bicarbazolyl;3,3'-Bi-9H-carbazole, 9-phenyl-;9-Phenyl-3,3'-bicarbazolyl;9-phenyl-3,3'-bicarbazole
• CAS NO: 1060735-14-9
• Molecular Formula: C₃₀H₂₀N₂
• Molecular Weight: 408.4932
• EINECS: 1312995-182-4
• Mol File: 1060735-14-9.mol
• Article Data: 65

Chemical Properties

• Boiling Point: 685.6±37.0 °C(Predicted)
• Appearance: /
• Density: 1.23±0.1 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 17.10±0.30(Predicted)
• CAS DataBase Reference: 9-Phenyl-9H,9'H-[3,3']bicarbazolyl(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Phenyl-9H,9'H-[3,3']bicarbazolyl(1060735-14-9)
• EPA Substance Registry System: 9-Phenyl-9H,9'H-[3,3']bicarbazolyl(1060735-14-9)

Safety Data

• Hazardous Substances Data: 1060735-14-9(Hazardous Substances Data)

Usage

Application

9-phenyl-3,3’-bicarbazolyl is the intermediate to synthesis electronic materials, such as OLED.9-phenyl-3,3’-bicarbazolyl is a kind of organic electroluminescent materials to make OLED display screen, and this intermediate can be used in OLED series, such as Thiophene series, Fluorene series, Boronic Acid series and so on.

Synthetic route

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 3-bromo-9H-carbazole (1592-95-6) → 9-phenyl-3,3'-bicarbazole (1060735-14-9)

Conditions	Yield
Stage #1: N-phenyl-9H-carbazol-3-boronic acid; 3-bromo-9H-carbazole With potassium carbonate In ethanol; water; toluene for 0.5h; Inert atmosphere; Stage #2: With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine In ethanol; water; toluene for 2h; Reflux;	97%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 12h; Inert atmosphere; Reflux;	90%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water for 4h; Inert atmosphere; Reflux;	86%

3-bromo-9-phenyl-9H-carbazole (1153-85-1) + (9H-carbazol-3-yl)boronic acid → 9-phenyl-3,3'-bicarbazole (1060735-14-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 12h; Reflux;	90%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 65℃; for 18h;	73%

3-bromo-9H-carbazole (1592-95-6) + 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-9H-carbazole (1126522-69-7) → 9-phenyl-3,3'-bicarbazole (1060735-14-9)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In water; toluene for 5h; Inert atmosphere; Reflux;	87%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane for 4h; Inert atmosphere; Reflux;	80%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 24h; Inert atmosphere;	77%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 3-iodocarbazole (16807-13-9) → 9-phenyl-3,3'-bicarbazole (1060735-14-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 80℃; for 7h; Inert atmosphere;	84%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 80℃; for 7h; Inert atmosphere;	2.43 g

3-bromo-9-phenyl-9H-carbazole (1153-85-1) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (855738-89-5) → 9-phenyl-3,3'-bicarbazole (1060735-14-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium hydroxide In water; toluene at 80℃; for 12h; Inert atmosphere;	75%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 12h; Reflux;	61%

3-iodocarbazole (16807-13-9) + 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-9H-carbazole (1126522-69-7) → 9-phenyl-3,3'-bicarbazole (1060735-14-9)

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 85℃; for 48h; Inert atmosphere;	74%
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 85℃; for 48h; Suzuki coupling; Inert atmosphere;	74%

9H-carbazole (86-74-8) → 9-phenyl-3,3'-bicarbazole (1060735-14-9)

Conditions	Yield
With N-Bromosuccinimide In methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; N,N-dimethyl-formamide
Multi-step reaction with 4 steps 1: potassium carbonate; 18-crown-6 ether; tri-tert-butyl phosphine / tris-(dibenzylideneacetone)dipalladium(0) / toluene; xylene / 18 h / Inert atmosphere; Reflux 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 0 °C 3: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 6 h / 80 °C / Inert atmosphere 4: potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / tris-(dibenzylideneacetone)dipalladium(0) / toluene; water / 5 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0 °C 2: potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / tris-(dibenzylideneacetone)dipalladium(0) / toluene; water / 5 h / Inert atmosphere; Reflux View Scheme

bromobenzene (108-86-1) → 9-phenyl-3,3'-bicarbazole (1060735-14-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium carbonate; 18-crown-6 ether; tri-tert-butyl phosphine / tris-(dibenzylideneacetone)dipalladium(0) / toluene; xylene / 18 h / Inert atmosphere; Reflux 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 0 °C 3: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 6 h / 80 °C / Inert atmosphere 4: potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / tris-(dibenzylideneacetone)dipalladium(0) / toluene; water / 5 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 2 steps 1: potassium acetate; dibenzo-18-crown-6; copper / N,N-dimethyl-formamide / 4 h / 120 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 18 h / 65 °C View Scheme

3-bromo-9-phenyl-9H-carbazole (1153-85-1) → 9-phenyl-3,3'-bicarbazole (1060735-14-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 6 h / 80 °C / Inert atmosphere 2: potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / tris-(dibenzylideneacetone)dipalladium(0) / toluene; water / 5 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C 1.2: 8 h / 20 °C 2.1: potassium phosphate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 48 h / 85 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C 1.2: 12 h / 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol / 5 h / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C 1.2: -78 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 80 - 90 °C / Alkaline conditions View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: -78 °C / Inert atmosphere 1.3: 0.5 h / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 8 h / Reflux; Inert atmosphere View Scheme

N-phenylcarbazole (1150-62-5) → 9-phenyl-3,3'-bicarbazole (1060735-14-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0 °C 2: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 6 h / 80 °C / Inert atmosphere 3: potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / tris-(dibenzylideneacetone)dipalladium(0) / toluene; water / 5 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 4 steps 1.1: sulfuric acid; potassium iodate; potassium iodide / ethanol / 2 h / 75 °C 2.1: n-butyllithium / toluene; diethyl ether; hexane / 1 h / -45 - -5 °C / Inert atmosphere 2.2: 2 h / -45 °C / Inert atmosphere 3.1: hydrogenchloride / water; toluene; diethyl ether; hexane / 20 °C / Inert atmosphere 4.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; toluene / 7 h / 80 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 12 h / 20 °C 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; water / 12 h / Reflux View Scheme

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 3-bromo-9H-carbazole (1592-95-6) + tris-(o-tolyl)phosphine (6163-58-2) → 9-phenyl-3,3'-bicarbazole (1060735-14-9)

Conditions	Yield
With potassium carbonate; palladium diacetate In 1,2-dimethoxyethane; toluene

C24H26BNO2 → 9-phenyl-3,3'-bicarbazole (1060735-14-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / water; toluene; diethyl ether; hexane / 20 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; toluene / 7 h / 80 °C / Inert atmosphere View Scheme

3-iodo-9-phenyl-9H-carbazole (502161-03-7) → 9-phenyl-3,3'-bicarbazole (1060735-14-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: n-butyllithium / toluene; diethyl ether; hexane / 1 h / -45 - -5 °C / Inert atmosphere 1.2: 2 h / -45 °C / Inert atmosphere 2.1: hydrogenchloride / water; toluene; diethyl ether; hexane / 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; toluene / 7 h / 80 °C / Inert atmosphere View Scheme

3-bromo-9H-carbazole (1592-95-6) → 9-phenyl-3,3'-bicarbazole (1060735-14-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri-tert-butyl phosphine / toluene / 100 °C 2.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C 2.2: -78 - 20 °C 3.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 80 - 90 °C / Alkaline conditions View Scheme
Multi-step reaction with 2 steps 1: potassium acetate; dibenzo-18-crown-6; copper / N,N-dimethyl-formamide / 4 h / 120 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 18 h / 65 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; water / 12 h / 95 °C / Inert atmosphere 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran; dichloromethane / 2 h / 20 °C View Scheme

iodobenzene (591-50-4) → 9-phenyl-3,3'-bicarbazole (1060735-14-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri-tert-butyl phosphine / toluene / 100 °C 2.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C 2.2: -78 - 20 °C 3.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 80 - 90 °C / Alkaline conditions View Scheme
Multi-step reaction with 3 steps 1: potassium phosphate; copper(l) iodide / toluene / 12 h / Reflux 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 12 h / 20 °C 3: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; water / 12 h / Reflux View Scheme

iodobenzene (591-50-4) + 9H,9′H-[3,3′]bicarbazole (1984-49-2) → 9-phenyl-3,3'-bicarbazole (1060735-14-9)

Conditions	Yield
With copper; potassium carbonate In nitrobenzene at 180℃; for 4h; Inert atmosphere;	5.59 g

C36H34N2Si → 9-phenyl-3,3'-bicarbazole (1060735-14-9)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran; dichloromethane at 20℃; for 2h;	7.5 g

o-fluorobromobenzene (1072-85-1) + 9-phenyl-3,3'-bicarbazole (1060735-14-9) → C36H23BrN2

Conditions	Yield
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 170℃; for 24h; Inert atmosphere;	99%

9-phenyl-3,3'-bicarbazole (1060735-14-9) + 1-chlorobenzofuro[2,3-c]pyridine (1206975-68-9) → C41H25N3O (1345970-18-4)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) In xylene for 14h; Inert atmosphere; Reflux;	98%

9-phenyl-3,3'-bicarbazole (1060735-14-9) + 1,4-bromoiodobenzene (589-87-7) → 9-(4-bromophenyl)-9'-phenyl-9H,9'H-[3,3']bicarbazole (1268622-34-9)

Conditions	Yield
With copper; potassium carbonate; sodium hydrogensulfite In 1,2-dichloro-benzene at 170℃; for 19.5h; Inert atmosphere;	97%
With potassium phosphate; copper(l) iodide; ethylenediamine In toluene for 24h; Reflux;	80.1%
With potassium phosphate; ethylenediamine; copper(l) iodide In toluene for 24h; Reflux;	80.1%

9-phenyl-3,3'-bicarbazole (1060735-14-9) + 2-(2,4-difluorophenyl)pyridine (391604-55-0) → 9′,9‴-(4-(pyridin-2-yl)-1,3-phenylene)bis(9-phenyl-9H,9′H-3,3′-bicarbazole)

Conditions	Yield
With caesium carbonate In N,N-dimethyl acetamide at 190℃; for 23h; Sealed tube; Microwave irradiation;	96%

2,3-dichloroquinoxaline (2213-63-0) + 9-phenyl-3,3'-bicarbazole (1060735-14-9) → 9-(3-chloroquinoxalin-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h;	95%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 2.5h;	59%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 2.5h;	59%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h;	54%

9-phenyl-3,3'-bicarbazole (1060735-14-9) + (3-bromophenyl)(3-(dibenzo[b,d]furan-4-yl)phenyl)diphenylsilane (1414960-14-7) → C66H44N2OSi (1414960-46-5)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) In xylene Reflux; Inert atmosphere;	94%

bromobenzene (108-86-1) + 9-phenyl-3,3'-bicarbazole (1060735-14-9) → 9,9′-diphenyl-9H,9′H-3,3′-bicarbazole (52249-38-4, 57102-62-2)

Conditions	Yield
Stage #1: bromobenzene; 9-phenyl-3,3'-bicarbazole With potassium tert-butylate In toluene for 0.5h; Inert atmosphere; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; XPhos In toluene for 7h; Reflux;	93%
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene for 12h; Reflux; Inert atmosphere;	90%

9-phenyl-3,3'-bicarbazole (1060735-14-9) + 2-(4-fluorophenyl)-3-phenylquinoxaline (202264-97-9) → 9-phenyl-9'-[4-(3-phenylquinoxalin-2-yl)phenyl]-3,3'-bi(9H-carbazol) (1245801-43-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium t-butanolate In toluene at 80℃; for 6h;	92%

9-phenyl-3,3'-bicarbazole (1060735-14-9) + C21H12FN3 → C51H31N5

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium t-butanolate In toluene at 80℃; for 6h;	91%

9-phenyl-3,3'-bicarbazole (1060735-14-9) + 4-(3-bromophenyl)dibenzo[b,d]thiophene (1084334-28-0) → C48H30N2S (1340668-37-2)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 60℃; for 12h;	90%

9-phenyl-3,3'-bicarbazole (1060735-14-9) + C13H6BrNS (1442648-21-6) → C43H25N3S

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene for 4h; Reflux;	89%

9-phenyl-3,3'-bicarbazole (1060735-14-9) + 7-fluoro-1-phenylbenzo[a]imidazo[5,1,2-cd]indolizine → C49H30N4

Conditions	Yield
With potassium phosphate In 1-methyl-pyrrolidin-2-one at 160℃; for 22h; Inert atmosphere;	89%

4-(4-bromophenyl)dibenzofuran (955959-84-9) + 9-phenyl-3,3'-bicarbazole (1060735-14-9) → C48H30N2O

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 60℃; for 12h; Inert atmosphere;	88%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene; toluene for 15h; Inert atmosphere; Reflux;	73%
With tris-(dibenzylideneacetone)dipalladium(0); trineopentyl phosphine; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene; toluene for 15h; Inert atmosphere; Reflux;	73%

9-phenyl-3,3'-bicarbazole (1060735-14-9) + C24H14Br2N2 → C84H52N6

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 12h; Inert atmosphere; Reflux;	88%

9-phenyl-3,3'-bicarbazole (1060735-14-9) + 2,4-bis(4-fluorophenyl)-6-phenyl-1,3,5-triazine (157141-82-7) → C81H51N7

Conditions	Yield
Stage #1: 2,4-bis(p-fluorophenyl)-6-phenyl-1,3,5-triazine With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 9-phenyl-3,3'-bicarbazole In N,N-dimethyl-formamide at 20℃; for 1h;	87%

9-phenyl-3,3'-bicarbazole (1060735-14-9) + C15H8ClN3 → C45H27N5

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium t-butanolate In toluene at 80℃; for 6h;	87%

9-phenyl-3,3'-bicarbazole (1060735-14-9) + 2-chloro-4-phenylbenzo[4,5]thieno[2,3-d]pyrimidine → C46H28N4S

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 100℃;	86%

9-phenyl-3,3'-bicarbazole (1060735-14-9) + 2-chloro-4-(dibenzo[b,d]furan-4-yl)benzo[4,5]thieno[3,2-d]pyrimidine → C52H30N4OS

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 100℃;	86%

3-bromodibenzofuran (26608-06-0) + 9-phenyl-3,3'-bicarbazole (1060735-14-9) → C42H26N2O

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene Inert atmosphere; Reflux;	86%

9-phenyl-3,3'-bicarbazole (1060735-14-9) + C20H11BrN2S → C50H30N4S

Conditions	Yield
With potassium phosphate; copper(l) iodide; rac-diaminocyclohexane In 1,4-dioxane for 12h; Inert atmosphere; Reflux;	86%

2-bromodibenzothiophene (22439-61-8) + 9-phenyl-3,3'-bicarbazole (1060735-14-9) → 9-(dibenzo[b,d]thiophen-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (1340668-15-6)

Conditions	Yield
With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane In 1,4-dioxane for 24h; Reflux;	85%
With potassium phosphate; copper(l) iodide; (S,S)-1,2-diaminocyclohexane In 1,4-dioxane for 24h; Reflux;	85%
With potassium phosphate; copper(l) iodide; (S,S)-1,2-diaminocyclohexane In 1,4-dioxane for 24h; Reflux;	85%

9-phenyl-3,3'-bicarbazole (1060735-14-9) + 2-(4-bromophenyl)naphthyl[1,2-d]oxazole → C47H29N3O

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 6h; Inert atmosphere; Heating;	85%

9-phenyl-3,3'-bicarbazole (1060735-14-9) + 2-bromo-4-phenyldibenzofuran → C48H30N2O

Conditions	Yield
With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane In 1,4-dioxane for 24h; Reflux;	85%
With potassium phosphate; copper(l) iodide; (S,S)-1,2-diaminocyclohexane In 1,4-dioxane for 24h; Reflux;	85%

2-bromodibenzo[b,d]furan (86-76-0) + 9-phenyl-3,3'-bicarbazole (1060735-14-9) → C42H26N2O (1345143-16-9)

Conditions	Yield
With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane In 1,4-dioxane Reflux;	85%
With potassium phosphate; copper(l) iodide; (S,S)-1,2-diaminocyclohexane In 1,4-dioxane for 24h; Reflux;	85%

9-phenyl-3,3'-bicarbazole (1060735-14-9) + 3-bromobiphenyl (2113-57-7) → C42H28N2

Conditions	Yield
With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane In 1,4-dioxane for 24h; Reflux;	85%
With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine In 1,4-dioxane for 24h; Reflux;	85%
With potassium phosphate; copper(l) iodide; (S,S)-1,2-diaminocyclohexane In 1,4-dioxane for 24h; Reflux;	85%
With potassium phosphate; copper(l) iodide; (S,S)-1,2-diaminocyclohexane In 1,4-dioxane for 24h; Reflux;	85%
With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane In 1,4-dioxane for 24h; Reflux;	85%

9-phenyl-3,3'-bicarbazole (1060735-14-9) + 2-chloro-3-phenylquinoxaline (7065-92-1) → C44H28N4

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium t-butanolate In toluene at 80℃; for 6h;	85%

9-phenyl-3,3'-bicarbazole (1060735-14-9) + 2-bromobenzo[9,10]phenanthrene (19111-87-6) → C48H30N2 (1392844-41-5)

Conditions	Yield
With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene at 150℃; for 24h; Inert atmosphere;	85%

Upstream product

• 854952-58-2 N-phenyl-9H-carbazol-3-boronic acid 
• 16807-13-9 3-iodocarbazole 
• 502161-03-7 3-iodo-9-phenyl-9H-carbazole 
• 591-50-4 iodobenzene 
• 1984-49-2 9H,9′H-[3,3′]bicarbazole 
• 1153-85-1 3-bromo-9-phenyl-9H-carbazole 
• 851524-97-5 (9H-carbazol-3-yl)boronic acid 
• 1592-95-6 3-bromo-9H-carbazole 
• 6163-58-2 tris-(o-tolyl)phosphine 
• 1126522-69-7 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-9H-carbazole 
• 1150-62-5 N-phenylcarbazole 
• 108-86-1 bromobenzene 
• 86-74-8 9H-carbazole 
• 855738-89-5 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 9H-carbazole 

Downstream Products

• 1060735-15-0 9-phenyl-9'-[4-(10-phenyl-9-anthryl)phenyl]-3,3'-bi(9H-carbazole) 
• 1245801-46-0 9-phenyl-9'-[4-(5-phenyl-1,3,4-oxadiazole-2-yl)phenyl]-3,3'-bi(9H-carbazole) 
• 1245801-43-7 9-phenyl-9'-[4-(3-phenylquinoxalin-2-yl)phenyl]-3,3'-bi(9H-carbazol) 
• 1150-62-5 N-phenylcarbazole 
• 1340668-15-6 9-(dibenzo[b,d]thiophen-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole 
• 1345143-20-5 9-(dibenzo[b,d]thiophen-4-yl)-9?-phenyl-9H,9'H-3,3?-bicarbazole 
• 1345143-22-7 C₄₁H₂₅N₃S 
• 1345970-18-4 C₄₁H₂₅N₃O 
• 1345143-16-9 C₄₂H₂₆N₂O 
• 1266389-01-8 9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9'-phenyl-3,3'-bicarbazole 
• 1268622-37-2 diphenyl-[2-(9'-phenyl-9H,9'H-[3,3']bicarbazolyl-9-yl)9,9-dimethylfluoren-7-yl]amine 
• 1398394-59-6 9-(3-bromophenyl)-9’-phenyl-3 ,3’-bis-9H-carbazole 
• 1268622-34-9 9-(4-bromophenyl)-9'-phenyl-9H,9'H-[3,3']bicarbazole 
• 1398395-37-3 C₄₀H₂₅BrN₂ 

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