1028648-22-7

Basic information

• Product Name: 9-(biphenyl-4-yl)-3-boric acid-9H-carbazole
• Synonyms: 9-(biphenyl-4-yl)-3-boric acid-9H-carbazole;(9-([1,1'-biphenyl]-4-yl)-9H-carbazol- 3-yl)boronic acid;(9-([1,1'-biphenyl]4-yl)-9H-carbazol-3yl)boronic;9-(Biphenyl-4-yl)-9H-carbazol-3-yl)-boronic acid;[9-(4-Biphenylyl)-9H-carbazol-3-yl]boronic acid;9-(4-Biphenylyl)-3-boronic acid;9-(4-biphenylyl)carbazole-3-boronic acid
• CAS NO: 1028648-22-7
• Molecular Formula: C₂₄H₁₈BNO₂
• Molecular Weight: 363.21622
• Mol File: 1028648-22-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 555.9±60.0 °C(Predicted)
• Appearance: /
• Density: 1.18±0.1 g/cm3(Predicted)
• PKA: 8.81±0.30(Predicted)
• CAS DataBase Reference: 9-(biphenyl-4-yl)-3-boric acid-9H-carbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 9-(biphenyl-4-yl)-3-boric acid-9H-carbazole(1028648-22-7)
• EPA Substance Registry System: 9-(biphenyl-4-yl)-3-boric acid-9H-carbazole(1028648-22-7)

Safety Data

• Hazardous Substances Data: 1028648-22-7(Hazardous Substances Data)

Usage

General Description

9-(biphenyl-4-yl)-3-boric acid-9H-carbazole is a chemical compound consisting of a boric acid functional group attached to a 9H-carbazole core with a biphenyl moiety. 9-(biphenyl-4-yl)-3-boric acid-9H-carbazole has potential applications in organic electronics and material science due to its unique structural features and electronic properties. The presence of the boric acid group enhances the chemical reactivity and coordination abilities of the molecule, making it useful for synthesis of new materials and as a building block for organic semiconductors. Additionally, the conjugated structure of the 9H-carbazole and biphenyl groups make it a promising candidate for use in optoelectronic devices such as organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs). Overall, 9-(biphenyl-4-yl)-3-boric acid-9H-carbazole is a versatile compound with potential applications in various fields of science and technology.

Synthetic route

9-[1,1’-biphenyl-4-yl]-3-bromo-9H-carbazole (894791-46-9) + Trimethyl borate (121-43-7) → 9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7)

Conditions	Yield
Stage #1: 9-[1,1′-biphenyl-4-yl]-3-bromo-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 20h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane at 20℃; for 3h;	91%
Stage #1: 9-[1,1′-biphenyl-4-yl]-3-bromo-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane for 0.166667h;	75.2%

9-[1,1’-biphenyl-4-yl]-3-bromo-9H-carbazole (894791-46-9) → 9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7)

Conditions	Yield
Stage #1: 9-[1,1′-biphenyl-4-yl]-3-bromo-9H-carbazole With n-butyllithium at -78℃; Stage #2: With Trimethyl borate Stage #3: With hydrogenchloride

4-bromo-1,1'-biphenyl (92-66-0) → 9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7)

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

9-([1,1’-biphenyl]-4-yl)-9H-carbazole (6299-16-7) → 9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / dichloromethane 2: n-butyllithium / -78 °C View Scheme

9H-carbazole (86-74-8) → 9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7)

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

hydrogenchloride (7647-01-0) + 9-[1,1’-biphenyl-4-yl]-3-bromo-9H-carbazole (894791-46-9) + Trimethyl borate (121-43-7) → 9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7)

Conditions	Yield
With n-BuLi In dichloromethane boron substituted Br in CH2Cl2 at -78°C in presence of n-BuLi andHCl;

3-bromo-9H-carbazole (1592-95-6) + 4-iodo-biphenyl (1591-31-7) → 9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); tributylphosphine / toluene / 12 h / Heating 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.2: 1 h / -78 - 20 °C 2.3: 0.17 h View Scheme

3-bromo-9H-carbazole (1592-95-6) → 9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 18-crown-6 ether; 1,10-Phenanthroline; copper(l) iodide; potassium carbonate / 5,5-dimethyl-1,3-cyclohexadiene / 7 h / 130 - 135 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 1 h / -90 °C / Inert atmosphere; Heating 2.2: 1 h View Scheme

4-iodo-biphenyl (1591-31-7) → 9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 18-crown-6 ether; 1,10-Phenanthroline; copper(l) iodide; potassium carbonate / 5,5-dimethyl-1,3-cyclohexadiene / 7 h / 130 - 135 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 1 h / -90 °C / Inert atmosphere; Heating 2.2: 1 h View Scheme

9-[1,1’-biphenyl-4-yl]-3-bromo-9H-carbazole (894791-46-9) + boric acid tributyl ester (688-74-4) → 9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7)

Conditions	Yield
Stage #1: 9-[1,1′-biphenyl-4-yl]-3-bromo-9H-carbazole With n-butyllithium In tetrahydrofuran at -90℃; for 1h; Inert atmosphere; Heating; Stage #2: boric acid tributyl ester In tetrahydrofuran for 1h; Stage #3: With hydrogenchloride In tetrahydrofuran; water; Petroleum ether	0.7 mol

3-bromo-9H-carbazole (1592-95-6) + 9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) → 9-(4-biphenylyl)-3,3'-bicarbazole (1346669-48-4)

Conditions	Yield
Stage #1: 3-bromo-9H-carbazole; 9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid 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;	96%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water; toluene for 12h; Inert atmosphere; Reflux;	64%

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) + 4-bromo-7-nitrobenzo[c][1,2,5]thiadiazole (26460-78-6) → C30H18N4O2S

Conditions	Yield
With potassium carbonate In tetrahydrofuran; water Reflux; Inert atmosphere;	95%

9-[1,1’-biphenyl-4-yl]-3-bromo-9H-carbazole (894791-46-9) + 9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) → 9,9′-bis([1,1′-biphenyl]-4-yl)-9H,9′H-3,3′-bicarbazole

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water at 90℃; for 12h;	92%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 90℃; for 12h; Inert atmosphere;	92%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 90℃; for 12h; Inert atmosphere;	92%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 90℃; for 12h; Inert atmosphere;	92%

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) + C27H17IN2 → C51H33N3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 8h; Inert atmosphere; Reflux;	87%

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) + 7-bromo-2-chlorodibenzo[b,d]furan → 9-([1,1'-biphenyl]-4-yl)-3-(8-chlorodibenzo[b,d]furan-3-yl)-9H-carbazole

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In water; toluene at 110℃; for 8h;	87%

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) + C30H26BrN → C54H42N2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 12h; Inert atmosphere; Reflux;	85%

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) + 1-bromo-8-chlorodibenzo[b,d]furan → 9-([1,1'-biphenyl]-4-yl)-3-(8-chlorodibenzo[b,d]furan-1-yl)-9H-carbazole

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In water; toluene at 110℃; for 8h;	82%

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) + C20H9BrS2 → C44H25NS2

Conditions	Yield
With sodium carbonate In toluene at 75 - 90℃; Inert atmosphere;	80%

N-(4-bromophenyl)-N-phenyl-[1,1’-biphenyl]-4-amine (503299-24-9) + 9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) → (4-(9-(biphenyl-4-yl)-9H-carbazol-3-yl)-phenyl)-biphenyl-4-yl-phenyl-amine (1160294-72-3)

Conditions	Yield
With potassium carbonate; palladium diacetate; tris-(o-tolyl)phosphine In ethanol; water; toluene at 90℃; for 6.5h; Suzuki Coupling;	79%

5-bromo-1,2-diphenyl-1H-benzo[d]imidazole (760212-55-3) + 9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) → C43H29N3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 120℃; for 20h; Inert atmosphere;	79%

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) + 2-(4-bromophenyl)indole (6127-49-7) → C38H26N2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 90℃;	79%

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) + C20H8Br2O2 → C68H40N2O2

Conditions	Yield
With sodium carbonate In toluene at 75 - 90℃; Inert atmosphere;	78%

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) + C33H23Br → C57H39N

Conditions	Yield
With palladium diacetate; potassium carbonate; tricyclohexylphosphine In water; toluene at 70 - 80℃; Inert atmosphere;	77.35%

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + 9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) → C34H20ClN3S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In tetrahydrofuran; water at 80℃;	75%

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) + 6-bromo-9-phenyl-9H-pyrido[3,4-b]indole → C41H27N3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 120℃; for 28h; Inert atmosphere;	70%

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + 9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) → C34H20ClN3S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 80℃; Alkaline conditions;	70%

2,4-dichloroquinazoline (607-68-1) + 9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) → C32H20ClN3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 60℃; for 10h; Inert atmosphere;	70%

4,7-dibromobenzo[c][1,2,5]thiadiazole (15155-41-6) + 9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) → C30H18BrN3S

Conditions	Yield
With potassium carbonate In tetrahydrofuran; water Reflux; Inert atmosphere;	70%

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) + 4-bromo-9-phenyl-9H-pyrido[3,4-b]indole → C41H27N3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80 - 90℃;	69%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80 - 90℃;	69%

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) + 2,4‐dichlorobenzo[h]quinazoline → C36H22ClN3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 60℃; for 10h; Inert atmosphere;	68%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 60℃; for 10h; Inert atmosphere;	65%

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) + 2,4-dichlorobenzo[4,5]furan[3,2-d]pyrimidine (160199-95-1) → C34H20ClN3O

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 60℃; for 10h; Inert atmosphere;	66%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 60℃; for 10h; Inert atmosphere;	66%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 60℃; for 10h; Inert atmosphere;	60%

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) + 2,4-dichloro-6,6-dimethyl-6H-indeno[2,1-g]quinazoline → C41H28ClN3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 60℃; for 10h; Inert atmosphere;	66%

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) + 11,13-dichlorophenanthro[9,10-g]quinazoline → C44H26ClN3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 60℃; for 10h; Inert atmosphere;	66%

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) + C17H12Cl2N2 → C41H28ClN3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 60℃; for 10h; Inert atmosphere;	63%

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) + C14H6Cl2N2O → C38H22ClN3O

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 60℃; for 10h; Inert atmosphere;	62%

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) + 2,4-dichlorodibenzo[f,h]quinazoline → C40H24ClN3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 60℃; for 10h; Inert atmosphere;	62%

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) + C10H4Cl2N2O → C34H20ClN3O

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 60℃; for 10h; Inert atmosphere;	61%

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) + (4-bromo-phenyl)-(4-naphthalen-1-yl-phenyl)-biphenyl-4-yl-amine (1160294-70-1) → (4-(9-(biphenyl-4-yl)-9H-carbazol-3-yl)-phenyl)-(4-naphthalen-1-yl-phenyl)-biphenyl-4-yl-amine (1160294-77-8)

Conditions	Yield
With potassium carbonate; palladium diacetate; tris-(o-tolyl)phosphine In ethanol; water; toluene at 90℃; for 6.5h; Suzuki Coupling;	60%

Upstream product

• 894791-46-9 9-[1,1′-biphenyl-4-yl]-3-bromo-9H-carbazole 
• 688-74-4 boric acid tributyl ester 
• 1591-31-7 4-iodo-biphenyl 
• 1592-95-6 3-bromo-9H-carbazole 
• 121-43-7 Trimethyl borate 
• 7647-01-0 hydrogenchloride 
• 86-74-8 9H-carbazole 
• 6299-16-7 9-([1,1’-biphenyl]-4-yl)-9H-carbazole 
• 92-66-0 4-bromo-1,1'-biphenyl 

Downstream Products

• 1160294-72-3 (4-(9-(biphenyl-4-yl)-9H-carbazol-3-yl)-phenyl)-biphenyl-4-yl-phenyl-amine 
• 1160294-77-8 (4-(9-(biphenyl-4-yl)-9H-carbazol-3-yl)-phenyl)-(4-naphthalen-1-yl-phenyl)-biphenyl-4-yl-amine 
• 1160294-74-5 (4-(9-biphenyl-4-yl-9H-carbazol-3-yl)-phenyl)-(4-naphthalen-1-yl-phenyl)-phenyl-amine 
• 1385028-95-4 C₅₃H₃₅N₃ 

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