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

Used in Suzuki Reaction:
9-Phenyl-9H-carbazol-3-ylboronic acid is used as a coupling partner in the Suzuki reaction, a widely employed cross-coupling process for the formation of carbon-carbon bonds. This reaction is particularly useful for the synthesis of complex organic molecules and the construction of molecular frameworks in various chemical and pharmaceutical applications.
Used in the Synthesis of Alkyl-functionalized Organic Dyes:
9-Phenyl-9H-carbazol-3-ylboronic acid is used as a key intermediate in the synthesis of alkyl-functionalized organic dyes. These dyes possess unique optical and electronic properties, making them suitable for applications in various fields, such as solar energy conversion, light-emitting diodes (LEDs), and bioimaging.
Used in the Synthesis of Alkyl-functionalized Organic Dyes:
B-(9-Phenyl-9H-carbazol-3-yl)boronic acid is used as a precursor in the synthesis of alkyl-functionalized organic dyes. The introduction of alkyl groups to the carbazole moiety enhances the solubility and processability of the dyes, which is crucial for their performance in practical applications. These dyes can be employed in various industries, including electronics, photonics, and materials science, for the development of advanced functional materials.

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

• 462-06-6 fluorobenzene 
• 5419-55-6 Triisopropyl borate 
• 7732-18-5 water 
• 57103-20-5 3,6-dibromo-9-phenyl-9H-carbazole 
• 121-43-7 Trimethyl borate 
• 29874-83-7 2-chloro-4-phenylquinazoline 
• 1153-85-1 3-bromo-9-phenyl-9H-carbazole 
• 150-46-9 triethyl borate 
• 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 
• 1179540-48-7 9-(phenanthryl)-10-(3-(9-phenyl)carbazole-9-yl)anthracene 
• 1028648-28-3 3-(4'-bromo-[1,1'-biphenyl]-4-yl)-9-phenyl-9H-carbazole 
• 1267248-03-2 C₅₇H₄₂N₂ 
• 1060735-14-9 9-phenyl-3,3'-bicarbazole 
• 1345860-59-4 3,5-bis(9-phenylcarbazol-3-yl)bromobenzene 
• 1415804-07-7 C₅₀H₃₁N₅ 
• 1438894-25-7 3-(6-fluoropyridin-3-yl)-9-phenylcarbazole 
• 1438894-28-0 3-(5-acetylthiophen-2-yl)-9-phenylcarbazole 
• 1340669-17-1 C₄₈H₃₁N₃ 
• 1399855-46-9 C₄₈H₃₁N₃ 
• 1428635-15-7 C₃₆H₂₅ClN₂ 
• 1428635-17-9 C₃₆H₂₄N₂ 

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