(9-Phenyl-9H-carbazol-3-yl)boronic acid supplier

Name
9-Phenyl-9H-carbazol-3-ylboronic acid
EINECS 691-972-0
CAS No. 854952-58-2
Article Data65
CAS DataBase
Density 1.2 g/cm³
Solubility Slightly soluble in water.
Melting Point
Formula C₁₈H₁₄BNO₂
Boiling Point 466 °C at 760 mmHg
Molecular Weight 287.126
Flash Point 235.6 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Boronic acid, B-(9-phenyl-9H-carbazol-3-yl)-;9-phenyl-9H-carbazol-3-yl-3-boronic acid;(9-phenyl)carbazole-3-boronic acid;
PSA 45.39000
LogP 2.46350

Synthetic route

: 1153-85-1
3-bromo-9-phenyl-9H-carbazole

: 121-43-7
Trimethyl borate

: 7732-18-5
water

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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%

...Expand

: 1153-85-1
3-bromo-9-phenyl-9H-carbazole

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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%

: 1153-85-1
3-bromo-9-phenyl-9H-carbazole

: 121-43-7
Trimethyl borate

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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%

: 121-43-7
Trimethyl borate

: 29874-83-7
2-chloro-4-phenylquinazoline

: 7732-18-5
water

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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%

...Expand

: 1153-85-1
3-bromo-9-phenyl-9H-carbazole

: 5419-55-6
Triisopropyl borate

: 7732-18-5
water

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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

...Expand

: 1153-85-1
3-bromo-9-phenyl-9H-carbazole

: 5419-55-6
Triisopropyl borate

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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℃;

: 5419-55-6
Triisopropyl borate

: 7732-18-5
water

: 57103-20-5
3,6-dibromo-9-phenyl-9H-carbazole

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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%

...Expand

: 121-43-7
Trimethyl borate

: 502161-03-7
3-iodo-9-phenyl-9H-carbazole

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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%

: 5419-55-6
Triisopropyl borate

: 502161-03-7
3-iodo-9-phenyl-9H-carbazole

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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℃;

: 1153-85-1
3-bromo-9-phenyl-9H-carbazole

: 1776-66-5
triisopropylborane

: 7732-18-5
water

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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%

...Expand

: 121-43-7
Trimethyl borate

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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%

: 7647-01-0
hydrogenchloride

: 1153-85-1
3-bromo-9-phenyl-9H-carbazole

: 121-43-7
Trimethyl borate

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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;

...Expand

: 591-50-4
iodobenzene

potassium hexacyanoferrate (II): potassium hexacyanoferrate (II)

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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

: 1150-62-5
N-phenylcarbazole

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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

: 86-74-8
9H-carbazole

sodium-salt of/the/ benzoylamino-methanesulfonic acid: sodium-salt of/the/ benzoylamino-methanesulfonic acid

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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

: 591-50-4
iodobenzene

4-CF3C6H4COCr(CO)5(1-)NMe4(1+): 4-CF3C6H4COCr(CO)5(1-)NMe4(1+)

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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

: 86-74-8
9H-carbazole

2-(6-X-hexyloxy)tetrahydro-2H-pyran, X=halide: 2-(6-X-hexyloxy)tetrahydro-2H-pyran, X=halide

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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

: 502161-03-7
3-iodo-9-phenyl-9H-carbazole

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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

: 150-46-9
triethyl borate

: (9-phenylcarbazole-3-yl)lithium

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

Conditions	Yield
In diethyl ether at -78℃;

: 108-86-1
bromobenzene

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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

: 86-74-8
9H-carbazole

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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

: 1592-95-6
3-bromo-9H-carbazole

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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

: 591-50-4
iodobenzene

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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

: 7732-18-5
water

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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

: 105971-15-1
5-bromo-2-nitro-biphenyl

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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

: 98-80-6
phenylboronic acid

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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

: 343864-78-8
2-iodo-1-nitro-4-bromobenzene

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

Conditions

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

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 19752-55-7
1-bromo-3,5-dichlorobenzene

: 1369431-36-6
3-(3,5-dichlorophenyl)-9-phenyl-9H-carbazole

Conditions

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

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 577-19-5
2-nitrophenyl bromide

: 1260032-04-9
3-(2-nitrophenyl)-9-phenyl-9H-carbazole

Conditions

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%

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 534591-96-3
3,3',5,5'-(tetrabromo)benzophenone

: C85H54N4O

Conditions

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%

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 28320-31-2
2-bromo-9,9-dimethyl-9H-fluorene

: C33H25N

Conditions

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%

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 1592-95-6
3-bromo-9H-carbazole

: 1060735-14-9
9-phenyl-3,3'-bicarbazole

Conditions

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%

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 1150-62-5
N-phenylcarbazole

Conditions

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%

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 23674-20-6
9-bromo-10-phenylanthracene

: C38H25N

Conditions

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%

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 106-39-8
bromochlorobenzene

: 1026033-57-7
3-(3-chlorophenyl)-9-phenyl-9H-carbazole

Conditions

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%

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 626-55-1
3-Bromopyridine

: C23H16N2

Conditions

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

: 96-43-5
2-thienyl chloride

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: C22H15NS

Conditions

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

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 176242-91-4
5-bromo-3,4’-dihexyl-2,2’-bithiophene

: 3-[3,4’-dihexyl(2,2’-bithiophene)-5-yl]-9-phenylcarbazole

Conditions

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;

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: C30H19Br

: C48H31N

Conditions

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

: 872-31-1
3-Bromothiophene

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: C22H15NS

Conditions

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

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 4-(10-bromoanthracene-9-yl)-2,5-dimethylbenzonitrile

: C41H28N2

Conditions

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

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 4-(10-bromoanthracene-9-yl)benzonitrile

: 4-(10-(9-phenyl-9H-carbazol-3-yl)anthracen-9-yl)benzonitrile

Conditions

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%

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 1160294-91-6
bis-(4-(2-naphthyl)phenyl)-(4-bromo-phenyl)-amine

: 1160294-89-2
(4-(9-phenyl-9H-carbazol-3-yl)-phenyl)-bis-(4-(2-naphthyl)phenyl)-amine

Conditions

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

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 1361227-58-8
3-bromo-9,9’-spirobifluorene

: 3-(9,9'-spirobi[fluoren]-6-yl)-9-phenyl-9H-carbazole

Conditions

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%

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 3435-24-3
4-tert-butyl-6-chloro-pyrimidine

: 4-tert-butyl-6-(9-phenyl-9H-carbazol-3-yl)pyrimidine

Conditions

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

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 198964-46-4
2,7-dibromo-9,9-dioctylfluorene

: 3-(7-bromo-9,9-dioctyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazole

Conditions

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;

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 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

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

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 1133-80-8
2-bromo-9H-fluorene

: 3-(9H-fluoren-2-yl)-9-phenyl-9H-carbazole

Conditions

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%

: 188200-91-1
9,9-bis-(n-butyl)-2,7-dibromofluorene

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: C57H48N2

Conditions

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

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: C40H22BrN3

: C58H34N4

Conditions

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

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 107-41-5
2-methyl-2,4-pentanediol

: 2-(9-phenyl-9H-carbazol-3-yl)-4,4,6-trimethyl-1,3,2-dioxaborinane

Conditions

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

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 589-87-7
1,4-bromoiodobenzene

: 1028647-93-9
3-(4-bromophenyl)-9-phenyl-9H carbazole

Conditions

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%

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 4265-16-1
2-formylbenzo[b]furan

: 2-benzofuranyl(9-phenylcarbazol-3-yl)methanone

Conditions

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%

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 1153-85-1
3-bromo-9-phenyl-9H-carbazole

: 52249-38-4, 57102-62-2
9,9′-diphenyl-9H,9′H-3,3′-bicarbazole

Conditions

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%

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 1036750-83-0
6-bromo-[1,1'-biphenyl]-3-amine

: 1428635-14-6
C30H22N2

Conditions

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

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: 1467099-22-4
3'-bromo-10-phenyl-10H-spiro(acridine-9,9'-fluorene)

: 10-phenyl-3'-(9-phenyl-9H-carbazol-3-yl)-10H-spiro(acridine-9,9'-fluorene)

Conditions

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

: 854952-58-2
N-phenyl-9H-carbazol-3-boronic acid

: C22H14BrN

: C40H26N2

Conditions

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

(9-Phenyl-9H-carbazol-3-yl)boronic acid Specification

The systematic name of B-(9-phenyl-9H-carbazol-3-yl)boronic acid is (9-phenylcarbazol-3-yl)boronic acid. With the CAS registry number 854952-58-2, it is also named as (9-Phenyl-9H-carbazol-3-yl)boronic acid. In addition, its molecular formula is C₁₈H₁₄BNO₂ and its molecular weight is 287.12.

The other characteristics of B-(9-phenyl-9H-carbazol-3-yl)boronic acid can be summarized as: (1)ACD/LogP: 5.57; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.57; (4)ACD/LogD (pH 7.4): 5.55; (5)ACD/BCF (pH 5.5): 10031.88; (6)ACD/BCF (pH 7.4): 9689.51; (7)ACD/KOC (pH 5.5): 25452.1; (8)ACD/KOC (pH 7.4): 24583.47; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 45.39 Å²; (13)Index of Refraction: 1.638; (14)Molar Refractivity: 85.79 cm³; (15)Molar Volume: 238.6 cm³; (16)Polarizability: 34.01×10^-24cm³; (17)Surface Tension: 47.9 dyne/cm; (18)Density: 1.2 g/cm³; (19)Flash Point: 235.6 °C; (20)Enthalpy of Vaporization: 76.67 kJ/mol; (21)Boiling Point: 466 °C at 760 mmHg; (22)Vapour Pressure: 1.74E-09 mmHg at 25 °C.

People can use the following data to convert to the molecule structure.
(1)SMILES: B(c1ccc2c(c1)c3ccccc3n2c4ccccc4)(O)O
(2)InChI: InChI=1/C18H14BNO2/c21-19(22)13-10-11-18-16(12-13)15-8-4-5-9-17(15)20(18)14-6-2-1-3-7-14/h1-12,21-22H
(3)InChIKey: JWJQEUDGBZMPAX-UHFFFAOYAQ
(4)Std. InChI: InChI=1S/C18H14BNO2/c21-19(22)13-10-11-18-16(12-13)15-8-4-5-9-17(15)20(18)14-6-2-1-3-7-14/h1-12,21-22H
(5)Std. InChIKey: JWJQEUDGBZMPAX-UHFFFAOYSA-N

Product Name

9-Phenyl-9H-carbazol-3-ylboronic acid

Synthetic route

(9-Phenyl-9H-carbazol-3-yl)boronic acid Specification

Related Products

Hot Products