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1028648-22-7

Basic Information
CAS No.: 1028648-22-7
Name: 9-(biphenyl-4-yl)-3-boric acid-9H-carbazole
Article Data: 11
Molecular Structure:
Molecular Structure of 1028648-22-7 (9-(biphenyl-4-yl)-3-boric
acid-9H-carbazole)
Formula: C24H18BNO2
Molecular Weight: 363.223
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
Density: 1.18±0.1 g/cm3(Predicted)
Boiling Point: 555.9±60.0 °C(Predicted)
PSA: 45.39000
LogP: 4.13050
Synthetic route
894791-46-9

9-[1,1’-biphenyl-4-yl]-3-bromo-9H-carbazole

121-43-7

Trimethyl borate

1028648-22-7

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid

Conditions
ConditionsYield
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%
894791-46-9

9-[1,1’-biphenyl-4-yl]-3-bromo-9H-carbazole

1028648-22-7

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid

Conditions
ConditionsYield
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
92-66-0

4-bromo-1,1'-biphenyl

1028648-22-7

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid

Conditions
ConditionsYield
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
6299-16-7

9-([1,1’-biphenyl]-4-yl)-9H-carbazole

1028648-22-7

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / dichloromethane
2: n-butyllithium / -78 °C
View Scheme
86-74-8

9H-carbazole

1028648-22-7

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid

Conditions
ConditionsYield
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
7647-01-0

hydrogenchloride

894791-46-9

9-[1,1’-biphenyl-4-yl]-3-bromo-9H-carbazole

121-43-7

Trimethyl borate

1028648-22-7

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid

Conditions
ConditionsYield
With n-BuLi In dichloromethane boron substituted Br in CH2Cl2 at -78°C in presence of n-BuLi andHCl;
1592-95-6

3-bromo-9H-carbazole

1591-31-7

4-iodo-biphenyl

1028648-22-7

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid

Conditions
ConditionsYield
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
1592-95-6

3-bromo-9H-carbazole

1028648-22-7

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid

Conditions
ConditionsYield
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
1591-31-7

4-iodo-biphenyl

1028648-22-7

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid

Conditions
ConditionsYield
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
894791-46-9

9-[1,1’-biphenyl-4-yl]-3-bromo-9H-carbazole

688-74-4

boric acid tributyl ester

1028648-22-7

9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid

Conditions
ConditionsYield
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
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    Chemical Name N-(biphenyl-4-yl)-3-carbazoleboronic acid CAS No. 1028648-22-7 Molecular Formula C24H18BNO2 Molecular Weight 363.21600 PSA

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