854952-58-2

Basic information

• Product Name: 9-Phenyl-9H-carbazol-3-ylboronic acid
• Synonyms: (9-phenyl)carbazole-3-boronic acid pinacol ester;3-BAPC;B-[3-(9-phenyl-9H-carbazole-3-yl)phenyl]-boronic acid;(9-Phenylcarbazol-3-yl)boronic acid;Carbazol-9-phenyl-3-boronic acid;Boronic acid,B-(9-phenyl-9H-carbazol-3-yl)-;9-Phenyl-9H-carbazol-3-ylboronic acid;9-phenyl-9H-carbazol-3-yl-3-boronic acid
• CAS NO: 854952-58-2
• Molecular Formula: C₁₈H₁₄BNO₂
• Molecular Weight: 287.12026
• EINECS: 1308068-626-2
• Product Categories: organic chemicals and derivatives/others;OLED;OLED materials,pharm chemical,electronic
• Mol File: 854952-58-2.mol
• Article Data: 65

Chemical Properties

• Boiling Point: 466 °C at 760 mmHg
• Flash Point: 235.6 °C
• Appearance: /Solid
• Density: 1.20
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly, Heated, Sonicated)
• PKA: 8.85±0.30(Predicted)
• Water Solubility: Slightly soluble in water.
• Stability: Hygroscopic
• CAS DataBase Reference: 9-Phenyl-9H-carbazol-3-ylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Phenyl-9H-carbazol-3-ylboronic acid(854952-58-2)
• EPA Substance Registry System: 9-Phenyl-9H-carbazol-3-ylboronic acid(854952-58-2)

Safety Data

• Hazardous Substances Data: 854952-58-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 854952-58-2 differently. You can refer to the following data:
1. 9-Phenyl-9H-carbazol-3-ylboronic acid is suzuki reaction
2. 9-Phenyl-9H-carbazol-3-ylboronic acidis used in the synthesis of alkyl-functionalized organic dyes.
3. B-(9-Phenyl-9H-carbazol-3-yl)boronic Acid is used in the synthesis of alkyl-functionalized organic dyes.

Synthetic route

3-bromo-9-phenyl-9H-carbazole (1153-85-1) + Trimethyl borate (121-43-7) + water (7732-18-5) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran for 0.5h; Inert atmosphere; Stage #3: water With hydrogenchloride In tetrahydrofuran Inert atmosphere;	90.2%
Stage #1: 3-bromo-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;	82.4%
Stage #1: 3-bromo-9-phenyl-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%
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere; Stage #3: water With hydrogenchloride at 20℃; for 0.5h;	67%

3-bromo-9-phenyl-9H-carbazole (1153-85-1) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -80℃; for 1h; Inert atmosphere; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -80 - 20℃; for 15h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane for 1h;	86%
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -80℃; for 1h; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -80 - 20℃; for 15h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water at 20℃;	86%
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane Further stages.;	83%

3-bromo-9-phenyl-9H-carbazole (1153-85-1) + Trimethyl borate (121-43-7) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -80℃; for 1h; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -80 - 20℃; for 15h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane at 20℃; for 1h;	86%
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran at -80℃; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at -80 - 20℃; Stage #3: With hydrogenchloride; water In tetrahydrofuran at 20℃; for 1h;	86%
With hydrogenchloride; n-butyllithium; magnesium sulfate In tetrahydrofuran; hexane; chloroform	80%

Trimethyl borate (121-43-7) + 2-chloro-4-phenylquinazoline (29874-83-7) + water (7732-18-5) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
Stage #1: 2-chloro-4-phenylquinazoline 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;	82.4%

3-bromo-9-phenyl-9H-carbazole (1153-85-1) + Triisopropyl borate (5419-55-6) + water (7732-18-5) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h; Stage #2: Triisopropyl borate In diethyl ether; hexane at -78℃; Stage #3: water With hydrogenchloride In diethyl ether; hexane at 20℃;	82%
Stage #1: 3-bromo-9-phenyl-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: water With hydrogenchloride In diethyl ether; hexane

3-bromo-9-phenyl-9H-carbazole (1153-85-1) + Triisopropyl borate (5419-55-6) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 3h; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at 20℃; for 0.5h; Inert atmosphere;	80%
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran at -78 - 20℃; Inert atmosphere; Stage #3: With hydrogenchloride; water In tetrahydrofuran at -10℃; Inert atmosphere;	70%
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at 20℃; for 12h; Stage #3: With water In tetrahydrofuran; hexane	67.33%
Stage #1: 3-bromo-9-phenyl-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℃;

Triisopropyl borate (5419-55-6) + water (7732-18-5) + 3,6-dibromo-9-phenyl-9H-carbazole (57103-20-5) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
Stage #1: Triisopropyl borate; 3,6-dibromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -70 - -60℃; for 1h; Inert atmosphere; Stage #2: water With hydrogenchloride In tetrahydrofuran; hexane at -20℃; for 1h; Solvent; Inert atmosphere;	77%

Trimethyl borate (121-43-7) + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
Stage #1: 3-iodo-9-phenyl-9H-carbazole With magnesium In tetrahydrofuran at 75 - 80℃; for 12h; Stage #2: Trimethyl borate In tetrahydrofuran at 0℃; for 5h; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 2h; Cooling;	76%
Stage #1: 3-iodo-9-phenyl-9H-carbazole With water; magnesium In tetrahydrofuran at 75 - 80℃; for 12h; Stage #2: Trimethyl borate In tetrahydrofuran at -20 - 0℃; for 5h; Stage #3: With hydrogenchloride In tetrahydrofuran at 0 - 20℃; for 2h;	76%
Stage #1: 3-iodo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane	51%

Triisopropyl borate (5419-55-6) + 3-iodo-9-phenyl-9H-carbazole (502161-03-7) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
Stage #1: 3-iodo-9-phenyl-9H-carbazole With n-butyllithium In diethyl ether; hexane; toluene at -45 - -5℃; Inert atmosphere; Stage #2: Triisopropyl borate In diethyl ether; hexane; toluene at -45℃; for 2h; Stage #3: With hydrogenchloride; water In diethyl ether; hexane; toluene at 20℃;	70%
Stage #1: 3-iodo-9-phenyl-9H-carbazole With n-butyllithium In diethyl ether; hexane; toluene at -45 - -5℃; for 1h; Inert atmosphere; Stage #2: Triisopropyl borate In diethyl ether; hexane; toluene at -45℃; for 2h; Stage #3: With hydrogenchloride; water In diethyl ether; hexane; toluene at 20℃; Product distribution / selectivity;
Stage #1: 3-iodo-9-phenyl-9H-carbazole With n-butyllithium In diethyl ether; hexane; toluene at -45 - -5℃; for 1h; Inert atmosphere; Stage #2: Triisopropyl borate In diethyl ether; hexane; toluene at -45℃; for 2h; Inert atmosphere; Stage #3: With hydrogenchloride In diethyl ether; hexane; water; toluene at 20℃; Inert atmosphere;
Stage #1: 3-iodo-9-phenyl-9H-carbazole With n-butyllithium In hexane; toluene at -45 - -5℃; for 1h; Inert atmosphere; Stage #2: Triisopropyl borate In hexane; toluene at -45℃; for 2h; Stage #3: With hydrogenchloride In hexane; water; toluene at 20℃;

3-bromo-9-phenyl-9H-carbazole (1153-85-1) + triisopropylborane (1776-66-5) + water (7732-18-5) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h; Stage #2: triisopropylborane In diethyl ether; hexane at -78 - 20℃; Stage #3: water With hydrogenchloride In diethyl ether; hexane	70%

Trimethyl borate (121-43-7) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 3h; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 24h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water at 20℃; for 1h;	58%

hydrogenchloride (7647-01-0) + 3-bromo-9-phenyl-9H-carbazole (1153-85-1) + Trimethyl borate (121-43-7) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: Trimethyl borate In tetrahydrofuran for 2h; Stage #3: hydrogenchloride In tetrahydrofuran; water	47%
With n-BuLi In dichloromethane boron substituted Br in CH2Cl2 at -78°C in presence of n-BuLi andHCl;

iodobenzene (591-50-4) + potassium hexacyanoferrate (II) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 87 percent / K2CO3; CuI; 1,10-phenanthroline / p-xylene / 180 °C 2.1: 94 percent / N-bromosuccinimide / dimethylformamide / 0 °C 3.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 3.2: (i-PrO)3B / tetrahydrofuran; hexane / -78 - 20 °C 3.3: 83 percent / aq. HCl / tetrahydrofuran; hexane View Scheme

N-phenylcarbazole (1150-62-5) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 94 percent / N-bromosuccinimide / dimethylformamide / 0 °C 2.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 2.2: (i-PrO)3B / tetrahydrofuran; hexane / -78 - 20 °C 2.3: 83 percent / aq. HCl / tetrahydrofuran; hexane View Scheme
Multi-step reaction with 2 steps 1: NBS / dimethylformamide / 0 °C 2: n-BuLi; (i-PrO)3B; HCl / tetrahydrofuran; H2O / -78 °C View Scheme
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / ethyl acetate; toluene / 45 h / 20 °C 2.1: n-butyllithium / hexane; tetrahydrofuran / 2 h / -78 °C 2.2: 24 h / 20 °C 2.3: 1 h / 20 °C View Scheme

9H-carbazole (86-74-8) + sodium-salt of/the/ benzoylamino-methanesulfonic acid → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 87 percent / K2CO3; CuI; 1,10-phenanthroline / p-xylene / 180 °C 2.1: 94 percent / N-bromosuccinimide / dimethylformamide / 0 °C 3.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 3.2: (i-PrO)3B / tetrahydrofuran; hexane / -78 - 20 °C 3.3: 83 percent / aq. HCl / tetrahydrofuran; hexane View Scheme

iodobenzene (591-50-4) + 4-CF3C6H4COCr(CO)5(1-)NMe4(1+) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: K2CO3; CuI; 1,10-phenanthroline / p-xylene / 180 °C 2: NBS / dimethylformamide / 0 °C 3: n-BuLi; (i-PrO)3B; HCl / tetrahydrofuran; H2O / -78 °C View Scheme

9H-carbazole (86-74-8) + 2-(6-X-hexyloxy)tetrahydro-2H-pyran, X=halide → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: K2CO3; CuI; 1,10-phenanthroline / p-xylene / 180 °C 2: NBS / dimethylformamide / 0 °C 3: n-BuLi; (i-PrO)3B; HCl / tetrahydrofuran; H2O / -78 °C View Scheme

3-iodo-9-phenyl-9H-carbazole (502161-03-7) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
Stage #1: 3-iodo-9-phenyl-9H-carbazole With n-butyllithium In diethyl ether; hexane; toluene at -45 - -5℃; for 1h; Stage #2: With isopropyldiisopropoxyborane In diethyl ether; hexane; toluene at -45℃; for 2h; Stage #3: With hydrogenchloride; water In diethyl ether; hexane; toluene at 20℃;
Multi-step reaction with 2 steps 1: n-butyllithium / 15 h / -78 - 20 °C 2: hydrogenchloride / water / 1 h View Scheme
Stage #1: 3-iodo-9-phenyl-9H-carbazole With n-butyllithium In diethyl ether; hexane; toluene at -45 - 5℃; for 1h; Inert atmosphere; Stage #2: With Triisopropyl borate In diethyl ether; hexane; toluene for 2h;
Stage #1: 3-iodo-9-phenyl-9H-carbazole With n-butyllithium In diethyl ether; hexane; toluene at -45 - -5℃; for 3h; Inert atmosphere; Stage #2: With Triisopropyl borate In diethyl ether; hexane; toluene at -45 - 20℃; Stage #3: With hydrogenchloride In diethyl ether; hexane; toluene at 20℃;	7.1 g
Multi-step reaction with 2 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 View Scheme

C20H18BNO2 → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; hexane; water for 1h;
With hydrogenchloride
With hydrogenchloride In water for 1h;

triethyl borate (150-46-9) + (9-phenylcarbazole-3-yl)lithium → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
In diethyl ether at -78℃;

bromobenzene (108-86-1) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: copper(l) iodide; 1,10-Phenanthroline; potassium carbonate 2: N-Bromosuccinimide / dichloromethane 3: n-butyllithium / -78 °C View Scheme
Multi-step reaction with 3 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 View Scheme
Multi-step reaction with 3 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 View Scheme

9H-carbazole (86-74-8) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: copper(l) iodide; 1,10-Phenanthroline; potassium carbonate 2: N-Bromosuccinimide / dichloromethane 3: n-butyllithium / -78 °C View Scheme
Multi-step reaction with 3 steps 1.1: copper; potassium carbonate / 1,2-dichloro-benzene / 12 h / Reflux 2.1: N-Bromosuccinimide / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C / Inert atmosphere 3.2: 4.5 h / -78 - 20 °C View Scheme
Multi-step reaction with 3 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 View Scheme

3-bromo-9H-carbazole (1592-95-6) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
Multi-step reaction with 2 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 View Scheme
Multi-step reaction with 3 steps 1.1: copper; 18-crown-6 ether; sodium t-butanolate / toluene / 24 h / 100 °C 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C 2.2: 1 h / -78 °C 3.1: hydrogenchloride / 1 h / 20 °C View Scheme
Multi-step reaction with 2 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 View Scheme

C24H26BNO2 → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
With hydrogenchloride In diethyl ether; hexane; water; toluene at 20℃; Inert atmosphere;	7.1 g

iodobenzene (591-50-4) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: copper; potassium carbonate / 1,2-dichloro-benzene / 12 h / Reflux 2.1: N-Bromosuccinimide / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C / Inert atmosphere 3.2: 4.5 h / -78 - 20 °C View Scheme
Multi-step reaction with 2 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 View Scheme
Multi-step reaction with 3 steps 1.1: copper; 18-crown-6 ether; sodium t-butanolate / toluene / 24 h / 100 °C 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C 2.2: 1 h / -78 °C 3.1: hydrogenchloride / 1 h / 20 °C View Scheme

C20H18BNO2 + water (7732-18-5) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
With hydrogenchloride at 20℃; for 1h;

5-bromo-2-nitro-biphenyl (105971-15-1) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

Conditions	Yield
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
Multi-step reaction with 3 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 View Scheme
Multi-step reaction with 3 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 View Scheme

phenylboronic acid (98-80-6) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

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 / 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 View Scheme
Multi-step reaction with 4 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 View Scheme

2-iodo-1-nitro-4-bromobenzene (343864-78-8) → N-phenyl-9H-carbazol-3-boronic acid (854952-58-2)

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 / 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 View Scheme
Multi-step reaction with 4 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 View Scheme

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 1-bromo-3,5-dichlorobenzene (19752-55-7) → 3-(3,5-dichlorophenyl)-9-phenyl-9H-carbazole (1369431-36-6)

Conditions	Yield
With potassium carbonate; palladium diacetate; tris-(o-tolyl)phosphine In ethanol; water; toluene at 80℃; for 7h; Suzuki-Miyaura reaction; Inert atmosphere;	100%
With tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate In ethanol; water; toluene for 10h; Reflux; Inert atmosphere;	3.0 g

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 2-nitrophenyl bromide (577-19-5) → 3-(2-nitrophenyl)-9-phenyl-9H-carbazole (1260032-04-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene at 120℃; for 3h;	99%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 24h; Reflux;	92%
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In tetrahydrofuran; water at 80℃;	86.7%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 3,3',5,5'-(tetrabromo)benzophenone (534591-96-3) → C85H54N4O

Conditions	Yield
Stage #1: N-phenyl-9H-carbazol-3-boronic acid; 3,3',5,5'-(tetrabromo)benzophenone With potassium phosphate In 5,5-dimethyl-1,3-cyclohexadiene; ethanol; water for 1h; Inert atmosphere; Stage #2: With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) In 5,5-dimethyl-1,3-cyclohexadiene; ethanol; water for 12h; Reflux;	98%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 2-bromo-9,9-dimethyl-9H-fluorene (28320-31-2) → C33H25N

Conditions	Yield
With potassium phosphate tribasic trihydrate; C44H43B10Br2P; palladium diacetate In ethanol; toluene at 120℃; for 36h; Kinetics; Reagent/catalyst; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	98%

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%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) → N-phenylcarbazole (1150-62-5)

Conditions	Yield
With silver nitrate; triethylamine In ethanol; water at 80℃; for 0.25h;	97%
With copper(ll) sulfate pentahydrate; oxygen; diisopropylamine In ethanol; water at 80℃; for 1.5h; Green chemistry;	64%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 9-bromo-10-phenylanthracene (23674-20-6) → C38H25N

Conditions	Yield
With potassium phosphate tribasic trihydrate; C44H43B10Br2P; palladium diacetate In ethanol; toluene at 120℃; for 36h; Kinetics; Reagent/catalyst; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	97%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 24h; Inert atmosphere; Reflux;	76%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 24h; Inert atmosphere; Reflux;	76%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + bromochlorobenzene (106-39-8) → 3-(3-chlorophenyl)-9-phenyl-9H-carbazole (1026033-57-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 8h; Inert atmosphere; Reflux;	97%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 8h; Inert atmosphere;	97%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 3-Bromopyridine (626-55-1) → C23H16N2

Conditions	Yield
With potassium carbonate In water; toluene at 90℃; for 0.5h; Suzuki-Miyaura Coupling;	97%

2-thienyl chloride (96-43-5) + N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) → C22H15NS

Conditions	Yield
With potassium carbonate In water; toluene at 90℃; for 2h; Suzuki-Miyaura Coupling;	97%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 5-bromo-3,4’-dihexyl-2,2’-bithiophene (176242-91-4) → 3-[3,4’-dihexyl(2,2’-bithiophene)-5-yl]-9-phenylcarbazole

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In toluene for 12h; Suzuki Coupling; Reflux; Inert atmosphere;	96%
With tetrakis(triphenylphosphine) palladium(0); Aliquat 336; potassium carbonate In tetrahydrofuran for 68h; Suzuki coupling; Reflux;

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + C30H19Br → C48H31N

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 120℃; for 3h;	96%

3-Bromothiophene (872-31-1) + N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) → C22H15NS

Conditions	Yield
With potassium carbonate In water; toluene at 90℃; for 0.5h; Suzuki-Miyaura Coupling;	96%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 4-(10-bromoanthracene-9-yl)-2,5-dimethylbenzonitrile → C41H28N2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 110℃; for 12h; Suzuki Coupling; Inert atmosphere;	95.39%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 4-(10-bromoanthracene-9-yl)benzonitrile → 4-(10-(9-phenyl-9H-carbazol-3-yl)anthracen-9-yl)benzonitrile

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 110℃; for 12h; Inert atmosphere;	95.36%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 110℃; for 12h; Suzuki Coupling; Inert atmosphere;	95.36%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 12h; Suzuki Coupling; Inert atmosphere;	79.61%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + bis-(4-(2-naphthyl)phenyl)-(4-bromo-phenyl)-amine (1160294-91-6) → (4-(9-phenyl-9H-carbazol-3-yl)-phenyl)-bis-(4-(2-naphthyl)phenyl)-amine (1160294-89-2)

Conditions	Yield
With potassium carbonate; palladium diacetate; tris-(o-tolyl)phosphine In ethanol; water; toluene at 90℃; for 14h; Suzuki Coupling;	95%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 3-bromo-9,9’-spirobifluorene (1361227-58-8) → 3-(9,9'-spirobi[fluoren]-6-yl)-9-phenyl-9H-carbazole

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 60℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere;	95%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 70℃; Suzuki-Miyaura Coupling; Inert atmosphere;	90%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 4-tert-butyl-6-chloro-pyrimidine (3435-24-3) → 4-tert-butyl-6-(9-phenyl-9H-carbazol-3-yl)pyrimidine

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; N,N-dimethyl-formamide for 1h; Microwave irradiation; Inert atmosphere;	95%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 2,7-dibromo-9,9-dioctylfluorene (198964-46-4) → 3-(7-bromo-9,9-dioctyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazole

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In tetrahydrofuran; water at 78℃; for 12h; Suzuki Coupling; Inert atmosphere;	95%
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In tetrahydrofuran; water at 78℃; for 12h; Inert atmosphere;

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 12-bromo-15H-diindolo[2,3-b:1',2',3'-lm]carbazole → 12-(9-phenyl-9H-carbazol-3-yl)-15H-diindolo[2,3-b:1',2',3'-lm]-carbazole

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 10h; Suzuki-Miyaura Coupling; Reflux;	95%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 2-bromo-9H-fluorene (1133-80-8) → 3-(9H-fluoren-2-yl)-9-phenyl-9H-carbazole

Conditions	Yield
With C35H40N4O9(2+)*2Cl(1-); palladium diacetate; potassium hydroxide In ethanol at 100℃; for 1.5h; Suzuki Coupling; Green chemistry;	94%
With potassium tert-butylate In ethanol; water Reflux;	92%
With palladium diacetate; potassium carbonate In ethanol; water at 110℃; for 1h; Suzuki Coupling; Inert atmosphere; Schlenk technique; Sealed tube;	89%

9,9-bis-(n-butyl)-2,7-dibromofluorene (188200-91-1) + N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) → C57H48N2

Conditions	Yield
With potassium tert-butylate In ethanol; water Reflux;	94%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + C40H22BrN3 → C58H34N4

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 5h; Inert atmosphere; Reflux;	93%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 2-methyl-2,4-pentanediol (107-41-5) → 2-(9-phenyl-9H-carbazol-3-yl)-4,4,6-trimethyl-1,3,2-dioxaborinane

Conditions	Yield
In dichloromethane at 20℃; for 16h;	93%

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) + 2-formylbenzo[b]furan (4265-16-1) → 2-benzofuranyl(9-phenylcarbazol-3-yl)methanone

Conditions	Yield
Stage #1: N-phenyl-9H-carbazol-3-boronic acid; 2-formylbenzo[b]furan With 1-(2,6-diisopropylphenyl)-3-(2-(phenylthio)phenyl)-4,5-dihydroimidazolinium chloride; bis(η3-allyl-μ-chloropalladium(II)); caesium carbonate In 1,4-dioxane at 100℃; for 1h; Inert atmosphere; Stage #2: With ortho-methylphenyl iodide In 1,4-dioxane at 100℃; for 15h; Inert atmosphere;	92%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 3-bromo-9-phenyl-9H-carbazole (1153-85-1) → 9,9′-diphenyl-9H,9′H-3,3′-bicarbazole (52249-38-4, 57102-62-2)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 12h; Inert atmosphere;	92%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 12h; Reflux;	92%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 12h; Reflux;	92%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 6-bromo-[1,1'-biphenyl]-3-amine (1036750-83-0) → C30H22N2 (1428635-14-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water; toluene for 15h; Inert atmosphere; Reflux;	92%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 3'-bromo-10-phenyl-10H-spiro(acridine-9,9'-fluorene) (1467099-22-4) → 10-phenyl-3'-(9-phenyl-9H-carbazol-3-yl)-10H-spiro(acridine-9,9'-fluorene)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 70℃; Suzuki-Miyaura Coupling; Inert atmosphere;	92%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + C22H14BrN → C40H26N2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 3h; Reflux; Inert atmosphere;	92%

Upstream product

• 121-43-7 Trimethyl borate 
• 150-46-9 triethyl borate 
• 29874-83-7 2-chloro-4-phenylquinazoline 
• 7732-18-5 water 
• 1153-85-1 3-bromo-9-phenyl-9H-carbazole 
• 462-06-6 fluorobenzene 
• 5419-55-6 Triisopropyl borate 
• 57103-20-5 3,6-dibromo-9-phenyl-9H-carbazole 
• 343864-78-8 4-bromo-2-iodo-1-nitrobenzene 
• 98-80-6 phenylboronic acid 
• 105971-15-1 5-bromo-2-nitro-biphenyl 
• 1776-66-5 triisopropylborane 
• 591-50-4 iodobenzene 
• 1592-95-6 3-bromo-9H-carbazole 

Downstream Products

• 1072194-21-8 N-phenyl-N-[4-(9-phenylcarbazole-3-yl)phenyl]amine 
• 1028648-35-2 C₄₉H₃₆N₂ 
• 1192650-81-9 3-(9,10-diphenyl-2-anthryl)-9-phenyl-9H-carbazole 
• 1350827-00-7 2-cyano-3-[3',4-di-n-hexyl-5'-(9-phenyl-9H-carbazol-3-yl)-[2,2']bithiophen-5-yl]acrylic acid 
• 1350826-98-0 C₂₈H₂₇NS 
• 1179540-48-7 9-(phenanthryl)-10-(3-(9-phenyl)carbazole-9-yl)anthracene 
• 854952-59-3 3-(3-bromophenyl)-9-phenyl-9H-carbazole 
• 1369431-36-6 3-(3,5-dichlorophenyl)-9-phenyl-9H-carbazole 
• 1240963-55-6 4-(9-phenyl-9H-carbazol-3-yl)phenylboronic acid 
• 1369431-19-5 3-[4-(9-phenanthryl)-phenyl]-9-phenyl-9H-carbazole 
• 1369431-21-9 9-phenyl-3-[4-(triphenylen-2-yl)-phenyl]-9H-carbazole 
• 1369431-33-3 9-phenyl-9H-3-{4-[3,5-di(phenanthren-9-yl)phenyl]phenyl}carbazole 
• 1365452-27-2 3-[4-(naphthalen-1-yl)phenyl]-9-phenyl-9H-carbazole 
• 1028648-28-3 3-(4'-bromo-[1,1'-biphenyl]-4-yl)-9-phenyl-9H-carbazole 

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