1001911-63-2

Basic information

• Product Name: (9-phenyl-9H-carbazol-2-yl)boronic acid
• Synonyms: (9-phenyl-9H-carbazol-2-yl)boronic acid (2PCBA);9-Phenylcarbazole-2-boronic acid;B-(9-Phenyl-9H-carbazol-2-yl)-boronic acid;2-BAPC;9-Phenylcarbazole-2-boronic Acid (contains varying amounts of Anhydride);(9-phenyl-9H-carbazol-2-yl)boronic acid;Boronic acid,B-(9-phenyl-9H-carbazol-2-yl)-
• CAS NO: 1001911-63-2
• Molecular Formula: C₁₈H₁₄BNO₂
• Molecular Weight: 287.12026
• Mol File: 1001911-63-2.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 466.0±51.0 °C(Predicted)
• Appearance: /
• Density: 1.20±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: very slightly in Tetrahydrofuran
• PKA: 8.91±0.30(Predicted)
• CAS DataBase Reference: (9-phenyl-9H-carbazol-2-yl)boronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (9-phenyl-9H-carbazol-2-yl)boronic acid(1001911-63-2)
• EPA Substance Registry System: (9-phenyl-9H-carbazol-2-yl)boronic acid(1001911-63-2)

Safety Data

• Hazardous Substances Data: 1001911-63-2(Hazardous Substances Data)

Usage

Uses

(9-phenyl-9H-carbazol-2-yl)boronic acid can be used as an intermediate in organic synthesis, mainly used in laboratory research and development and in the process of chemical and pharmaceutical synthesis.

Synthesis

Sub 1-3-1 (6.4g, 20mmol) was dissolved in anhydrous Ether, lowering the temperature of the reaction to -78°C, n-BuLi (2.5M in hexane) (1.4g, 22mmol) was added dropwise slowly, and after, the reaction It was stirred for 30 minutes. After lowering the temperature of the reaction back to -78°C dropwise Triisopropyl borate (5.6g, 30mmol). Stirring at room temperature, diluted with water and it binds the 2N HCl. After completion of reaction, ethyl acetate and water, dried over MgSO4 and the organic layer was extracted and recrystallized silicagel column and the resulting organic material and then concentrated to a Sub 1-4-1 4.5g (yield: 78%) was obtained.

Synthetic route

Triisopropyl borate (5419-55-6) + 9-(phenyl)-2-bromo-9H-carbazole (94994-62-4) → (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2)

Conditions	Yield
Stage #1: 9-(phenyl)-2-bromo-9H-carbazole With n-butyllithium In tetrahydrofuran at -75 - 0℃; for 1h; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran at -70 - 20℃; for 12h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water for 0.5h; Temperature; Inert atmosphere;	95%
Stage #1: 9-(phenyl)-2-bromo-9H-carbazole With n-butyllithium In tetrahydrofuran for 1h; Stage #2: Triisopropyl borate In tetrahydrofuran at 20℃; for 12h;	78.4%
Stage #1: 9-(phenyl)-2-bromo-9H-carbazole With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h; Stage #2: Triisopropyl borate In diethyl ether; hexane at -78 - 20℃; Stage #3: With hydrogenchloride In diethyl ether; hexane	78%
Stage #1: 9-(phenyl)-2-bromo-9H-carbazole With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: Triisopropyl borate In tetrahydrofuran	70%
Stage #1: 9-(phenyl)-2-bromo-9H-carbazole With n-butyllithium In tetrahydrofuran at -78℃; for 0.666667h; Stage #2: Triisopropyl borate In tetrahydrofuran at 20℃; for 12h; Stage #3: With water In tetrahydrofuran; hexane	62.8%

Trimethyl borate (121-43-7) + 9-(phenyl)-2-bromo-9H-carbazole (94994-62-4) + water (7732-18-5) → (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2)

Conditions	Yield
Stage #1: 9-(phenyl)-2-bromo-9H-carbazole With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 1h; Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 12h; Stage #3: water With hydrogenchloride In tetrahydrofuran	81%

Trimethyl borate (121-43-7) + 9-(phenyl)-2-bromo-9H-carbazole (94994-62-4) → (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2)

Conditions	Yield
Stage #1: 9-(phenyl)-2-bromo-9H-carbazole With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 1h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 12h;	79%
Stage #1: 9-(phenyl)-2-bromo-9H-carbazole With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;	72%
Stage #1: 9-(phenyl)-2-bromo-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: Trimethyl borate In tetrahydrofuran; hexane for 12h; Stage #3: With water	69%
With n-butyllithium
Stage #1: 9-(phenyl)-2-bromo-9H-carbazole With n-butyllithium at -78℃; Stage #2: Trimethyl borate at -78℃; Stage #3: With hydrogenchloride In water

hydrogenchloride (7647-01-0) + Trimethyl borate (121-43-7) + 9-(phenyl)-2-bromo-9H-carbazole (94994-62-4) → (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2)

Conditions	Yield
Stage #1: Trimethyl borate; 9-(phenyl)-2-bromo-9H-carbazole With n-butyllithium In tetrahydrofuran at -78 - 20℃; Stage #2: hydrogenchloride In tetrahydrofuran	76%

9-(phenyl)-2-bromo-9H-carbazole (94994-62-4) → (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2)

Conditions	Yield
Stage #1: 9-(phenyl)-2-bromo-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at 20℃; for 12h; Stage #3: With water In tetrahydrofuran; hexane	69%
Stage #1: 9-(phenyl)-2-bromo-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 12h; Stage #3: With water In tetrahydrofuran; hexane at 20℃;	67.33%
With hydrogenchloride; n-butyllithium; Trimethyl borate In water Inert atmosphere;

Triisopropyl borate (5419-55-6) + 9-(phenyl)-2-bromo-9H-carbazole (94994-62-4) + water (7732-18-5) → (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2)

Conditions	Yield
Stage #1: 9-(phenyl)-2-bromo-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane for 0.5h; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at 20℃; for 5h; Stage #3: water With hydrogenchloride In tetrahydrofuran; hexane; water for 0.5h;	55%

4-Bromophenylboronic acid (5467-74-3) → (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene / 4 h / 100 °C 2.1: triethyl phosphite / 6 h / 150 °C 3.1: caesium carbonate / copper(l) iodide / toluene / 50 °C 3.2: 14 h / Reflux 4.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C 4.2: 12 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene / 4 h / 100 °C 2.1: triethyl phosphite / 6 h / 150 °C 3.1: caesium carbonate / copper(l) iodide / toluene / 50 °C 3.2: 14 h / Reflux 4.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C 4.2: 12 h View Scheme

4'-bromo-2-nitrobiphenyl (35450-34-1) → (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethyl phosphite / 6 h / 150 °C 2.1: caesium carbonate / copper(l) iodide / toluene / 50 °C 2.2: 14 h / Reflux 3.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C 3.2: 12 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: triethyl phosphite / 6 h / 150 °C 2.1: caesium carbonate / copper(l) iodide / toluene / 50 °C 2.2: 14 h / Reflux 3.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C 3.2: 12 h View Scheme
Multi-step reaction with 3 steps 1.1: triethyl phosphate / 7 h / 150 °C 2.1: potassium phosphate; ethylenediamine / 12 h / Reflux 3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 3.2: 12 h / -78 - 20 °C 3.3: 20 °C View Scheme

2-bromo-9H-carbazole (3652-90-2) → (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: caesium carbonate / copper(l) iodide / toluene / 50 °C 1.2: 14 h / Reflux 2.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C 2.2: 12 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: caesium carbonate / copper(l) iodide / toluene / 50 °C 1.2: 14 h / Reflux 2.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C 2.2: 12 h View Scheme
Multi-step reaction with 2 steps 1.1: caesium carbonate; copper(l) iodide; ethylenediamine / toluene / 12 h / Reflux 2.1: n-butyllithium / tetrahydrofuran / 1 h 2.2: 12 h / 20 °C View Scheme

o-nitroiodobenzene (609-73-4) → (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene / 4 h / 100 °C 2.1: triethyl phosphite / 6 h / 150 °C 3.1: caesium carbonate / copper(l) iodide / toluene / 50 °C 3.2: 14 h / Reflux 4.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C 4.2: 12 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene / 4 h / 100 °C 2.1: triethyl phosphite / 6 h / 150 °C 3.1: caesium carbonate / copper(l) iodide / toluene / 50 °C 3.2: 14 h / Reflux 4.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C 4.2: 12 h View Scheme

1,4-dibromo-2-nitrobenzene (3460-18-2) → (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol; water / 24 h / Reflux 2.1: triethyl phosphite / 1,2-dichloro-benzene / 24 h / 150 °C 3.1: caesium carbonate; copper(l) iodide; ethylenediamine / toluene / 12 h / Reflux 4.1: n-butyllithium / tetrahydrofuran / 1 h 4.2: 12 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 24 h / Reflux 2.1: triethyl phosphite / 1,2-dichloro-benzene / 24 h / 150 °C 3.1: copper(l) iodide; ethylenediamine; caesium carbonate / toluene / 4 h / Reflux 4.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C 4.2: 12 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene / 90 °C 2.1: triethyl phosphite / Reflux 3.1: sodium hydroxide; copper(l) iodide; 1,10-Phenanthroline / para-xylene / 48 h / 140 °C 4.1: n-butyllithium / -78 °C 4.2: -78 °C View Scheme
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene / Inert atmosphere 2: triethyl phosphite / Inert atmosphere 3: copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide / para-xylene / Inert atmosphere 4: n-butyllithium; hydrogenchloride; Trimethyl borate / water / Inert atmosphere View Scheme

4-bromo-2-nitro-1-phenylbenzene (70873-41-5) → (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethyl phosphite / 1,2-dichloro-benzene / 24 h / 150 °C 2.1: caesium carbonate; copper(l) iodide; ethylenediamine / toluene / 12 h / Reflux 3.1: n-butyllithium / tetrahydrofuran / 1 h 3.2: 12 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: triethyl phosphite / 1,2-dichloro-benzene / 24 h / 150 °C 2.1: copper(l) iodide; ethylenediamine; caesium carbonate / toluene / 4 h / Reflux 3.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C 3.2: 12 h / 20 °C View Scheme
Multi-step reaction with 3 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 View Scheme

phenylboronic acid (98-80-6) → (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol; water / 24 h / Reflux 2.1: triethyl phosphite / 1,2-dichloro-benzene / 24 h / 150 °C 3.1: caesium carbonate; copper(l) iodide; ethylenediamine / toluene / 12 h / Reflux 4.1: n-butyllithium / tetrahydrofuran / 1 h 4.2: 12 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; toluene / 5 h / Reflux 2.1: iron(III) chloride; bromine / tetrachloromethane / 12 h / 0 - 20 °C 3.1: triethyl phosphate / 7 h / 150 °C 4.1: potassium phosphate; ethylenediamine / 12 h / Reflux 5.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 5.2: 12 h / -78 - 20 °C 5.3: 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 24 h / Reflux 2.1: triethyl phosphite / 1,2-dichloro-benzene / 24 h / 150 °C 3.1: copper(l) iodide; ethylenediamine; caesium carbonate / toluene / 4 h / Reflux 4.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C 4.2: 12 h / 20 °C View Scheme

2-nitrophenyl bromide (577-19-5) → (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; toluene / 5 h / Reflux 2.1: iron(III) chloride; bromine / tetrachloromethane / 12 h / 0 - 20 °C 3.1: triethyl phosphate / 7 h / 150 °C 4.1: potassium phosphate; ethylenediamine / 12 h / Reflux 5.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 5.2: 12 h / -78 - 20 °C 5.3: 20 °C View Scheme

2-nitrobiphenyl (86-00-0) → (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: iron(III) chloride; bromine / tetrachloromethane / 12 h / 0 - 20 °C 2.1: triethyl phosphate / 7 h / 150 °C 3.1: potassium phosphate; ethylenediamine / 12 h / Reflux 4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: 12 h / -78 - 20 °C 4.3: 20 °C View Scheme

iodobenzene (591-50-4) → (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate / toluene / 100 °C 2.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C 2.2: -78 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: copper(l) chloride; potassium carbonate / dimethyl sulfoxide / 24 h / Reflux 2.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 2.2: 4 h / 20 °C / Inert atmosphere View Scheme

1-iodo-4-bromo-2-nitrobenzene (112671-42-8) → (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2)

Conditions	Yield
Multi-step reaction with 4 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 View Scheme
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 24 h / 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 View Scheme

3-bromo-9H-carbazole (1592-95-6) + (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) → C30H20N2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene at 120℃; for 5h;	93%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water for 4h; Inert atmosphere; Reflux;	80%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 12h; Reflux;	80%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 5h; Reflux;	58.57%

(9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) + 3-(4-bromophenyl)-4-naphthyl-5-phenyl-1,2,4-triazole → C42H28N4

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 70℃; for 24h; Suzuki Coupling; Inert atmosphere;	93%

(9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) → N-phenyl-2-hydroxycarbazole

Conditions	Yield
With 2,5-dimethylfuran; zinc(II) phthalocyanine; oxygen In tetrahydrofuran at 25℃; under 760.051 Torr; for 2h; Time; Irradiation; Sealed tube; Schlenk technique;	93%
With oxygen; triethylamine In 2-methyltetrahydrofuran at 20℃; under 760.051 Torr; for 48h; Green chemistry;	85%
With oxygen; triethylamine In 2-methyltetrahydrofuran at 20℃; under 760.051 Torr; for 48h; UV-irradiation;	85%

2-nitrophenyl bromide (577-19-5) + (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) → 2-(2-nitrophenyl)-9-phenyl-9H-carbazole (1361125-94-1)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 12h; Inert atmosphere;	92%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 12h; Inert atmosphere;	87%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene for 5h; Reflux;	81.36%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene for 5h; Reflux;	81.36%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 120℃; for 24h; Inert atmosphere;	70.6%

trimethylsilyl cyanide (7677-24-9) + (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) → 9-phenyl-2-selenocyanato-9H-carbazole

Conditions	Yield
With selenium In dimethyl sulfoxide at 120℃; Schlenk technique; Green chemistry;	91%

(9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) + C42H31BF2I2N2 → C78H55BF2N4

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 12h; Reflux;	90%

(9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) + C37H22ClN → C55H34N2

Conditions	Yield
With potassium phosphate; bis(tri-t-butylphosphine)palladium(0) In 1,4-dioxane; water for 8h; Reflux;	90%

(9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) + C39H22BrNO2 → C57H34N2O2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 120℃; for 12h;	90%

9-[1,1’-biphenyl-4-yl]-3-bromo-9H-carbazole (894791-46-9) + (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) → C42H28N2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 12h; Reflux;	89%

2-bromo-11H-benzo[a]carbazole (103569-04-6) + (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) → C34H22N2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 3h; Inert atmosphere; Heating;	88%

(9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) + C18H8BrClS2 → C36H20ClNS2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In tetrahydrofuran; water for 6h;	88%

(9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) + 2-bromo-7-chlorodibenzo[b,d]thiophene → C30H18ClNS

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In tetrahydrofuran; water at 80℃; for 12h;	88%

(9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) + C29H20BrN3 → C47H32N4

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In tetrahydrofuran; water at 80 - 90℃;	86%

3-bromo-2-nitro-1-benzothiophene (17402-78-7) + (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) → 2-(2-nitrobenzo[b]thiophen-3-yl)-9-phenyl-9H-carbazole

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 100℃; for 6h; Inert atmosphere;	85%

2-bromo-3-nitrobenzo[b]thiophene (100949-37-9) + (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) → 2-(3-nitrobenzo[b]thiophen-2-yl)-9-phenyl-9H-carbazole

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 100℃; for 6h; Inert atmosphere;	85%

(9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) + C18H9BrClN → C36H21ClN2

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); potassium carbonate In tetrahydrofuran; water for 3h; Reflux;	84%

(9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) + 2-(2-(4-iodophenoxy)-1-phenylethyl)malononitrile → 2-(1-phenyl-2-(4-(9-phenyl-9H-carbazol-2-yl)phenoxy)ethyl)malononitrile

Conditions	Yield
With palladium diacetate; potassium carbonate; triphenylphosphine In ethanol; water; toluene at 100℃; for 24h;	83%
With palladium diacetate; potassium carbonate; triphenylphosphine In ethanol; water; toluene at 100℃; for 24h; Suzuki Coupling; Sealed tube; Inert atmosphere;	82%

(9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) + C34H24BrN3 → C52H36N4

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 12h; Inert atmosphere; Reflux;	82%

(9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) + C34H19BrO → C52H31NO

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 110℃; for 12h; Inert atmosphere;	82%

(9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) + C18H9BrClN → C36H21ClN2

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); potassium carbonate In tetrahydrofuran; water for 3h; Reflux;	81%

(9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) + C24H14BrN3S → C42H26N4S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 12h; Reflux; Inert atmosphere;	80%

(9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) + C33H19ClN4 → C51H31N5

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0) In 1,4-dioxane; water for 3h; Reflux;	80%

(9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) + C28H10F18O7S2 → C56H34N2O

Conditions	Yield
With potassium carbonate; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine In tetrahydrofuran for 5h; Reflux;	80%

1,6-dibromonaphthalene (19125-84-9) + (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) → C28H18BrN

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 110℃; Inert atmosphere;	79%

(9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) + C20H8Br2S2 → C56H32N2S2

Conditions	Yield
With sodium carbonate In toluene at 75 - 90℃; Inert atmosphere;	79%

(9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) + C20H8Br2O2 → C56H32N2O2

Conditions	Yield
With sodium carbonate In toluene at 75 - 90℃; Inert atmosphere;	79%

(9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) + C53H33BrN2 → C71H45N3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 12h; Inert atmosphere; Reflux;	79%

Upstream product

• 5419-55-6 Triisopropyl borate 
• 94994-62-4 9-(phenyl)-2-bromo-9H-carbazole 
• 7732-18-5 water 
• 112671-42-8 4-bromo-1-iodo-2-nitrobenzene 
• 121-43-7 Trimethyl borate 
• 591-50-4 iodobenzene 
• 86-00-0 2-nitrobiphenyl 
• 577-19-5 2-nitrophenyl bromide 
• 98-80-6 phenylboronic acid 
• 70873-41-5 4-bromo-2-nitro-1-phenylbenzene 
• 3460-18-2 1,4-dibromo-2-nitrobenzene 
• 609-73-4 o-nitroiodobenzene 
• 3652-90-2 2-bromo-9H-carbazole 
• 35450-34-1 4'-bromo-2-nitrobiphenyl 

Downstream Products

• 1361125-94-1 2-(2-nitrophenyl)-9-phenyl-9H-carbazole 
• 1316311-27-9 5-phenyl-5,11-dihydro-indolo[3,2-b]carbazole 
• 1369587-22-3 C₃₀H₁₉BrN₂ 
• 1369587-25-6 C₃₀H₂₁BN₂O₂ 
• 1369585-27-2 C₄₈H₃₀N₂ 
• 1415804-07-7 C₅₀H₃₁N₅ 
• 1382955-10-3 9-phenyl-9H,9'H-2,3'-bicarbazole 
• 1351692-34-6 C₂₄H₁₅Br₂N 

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