triethyl borate
2-(4-bromophenyl)-1-phenyl-1H-benzimidazole
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
Stage #1: 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole With n-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Inert atmosphere; Stage #2: triethyl borate In tetrahydrofuran; cyclohexane at 20℃; for 12h; Inert atmosphere; | 80% |
Triisopropyl borate
2-(4-bromophenyl)-1-phenyl-1H-benzimidazole
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | 74% |
Stage #1: 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃; | 58.3% |
Triisopropyl borate
water
2-(4-bromophenyl)-1-phenyl-1H-benzimidazole
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
Stage #1: Triisopropyl borate; 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Stage #2: water With hydrogenchloride In tetrahydrofuran; hexane | 74% |
hydrogenchloride
Trimethyl borate
2-(4-bromophenyl)-1-phenyl-1H-benzimidazole
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
Stage #1: 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole In tetrahydrofuran at -78℃; for 0.5h; Stage #2: With n-butyllithium at -78℃; for 0.5h; Stage #3: hydrogenchloride; Trimethyl borate Further stages; | 70% |
Trimethyl borate
water
2-(4-bromophenyl)-1-phenyl-1H-benzimidazole
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
Stage #1: 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: Trimethyl borate In tetrahydrofuran for 2h; Stage #3: water In tetrahydrofuran for 0.333333h; | 65% |
Stage #1: 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: Trimethyl borate In tetrahydrofuran for 2h; Stage #3: water With hydrogenchloride In tetrahydrofuran for 0.833333h; | 60% |
2-(4-bromophenyl)-1-phenyl-1H-benzimidazole
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
Stage #1: 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole With n-butyllithium; Trimethyl borate Stage #2: With hydrogenchloride In water |
4-Bromobenzoic acid
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: thionyl chloride / 1,2-dichloro-ethane / 3 h / Reflux 2.1: 1-methyl-pyrrolidin-2-one / 20 °C 3.1: acetic acid / 12 h / Reflux 4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 4.2: -78 - 20 °C View Scheme |
4-chlorobenzoyl chloride
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 1-methyl-pyrrolidin-2-one / 20 °C 2.1: acetic acid / 12 h / Reflux 3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 3.2: -78 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: triethylamine / 1-methyl-pyrrolidin-2-one / 20 °C 2: acetic acid / 12 h / Reflux 3: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: triethylamine / 1-methyl-pyrrolidin-2-one / 20 °C 2: acetic acid / 12 h / Reflux 3: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1.1: N,N-dimethyl acetamide 2.1: acetic acid / 0.5 h / 115 °C 3.1: TEFLON / tetrahydrofuran / 0.5 h / -78 °C 3.2: 0.5 h / -78 °C View Scheme |
4-bromo-N-(2-(phenylamino)phenyl)benzamide
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: acetic acid / 12 h / Reflux 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 2.2: -78 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: acetic acid / 12 h / Reflux 2: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: acetic acid / 12 h / Reflux 2: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1.1: acetic acid / 0.5 h / 115 °C 2.1: TEFLON / tetrahydrofuran / 0.5 h / -78 °C 2.2: 0.5 h / -78 °C View Scheme |
4-formylphenylboronic acid,
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 130 °C / Molecular sieve; Inert atmosphere 2: potassium iodide / N,N-dimethyl-formamide / 80 °C 3: sodium hydroxide / N,N-dimethyl-formamide; water / 0.5 h / 20 °C View Scheme |
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
With sodium hydroxide In water; N,N-dimethyl-formamide at 20℃; for 0.5h; |
4-formylphenylboronic acid
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium iodide / N,N-dimethyl-formamide / 80 °C 2: sodium hydroxide / N,N-dimethyl-formamide; water / 0.5 h / 20 °C View Scheme |
N-phenyl-1,2-benzenediamine
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: triethylamine / 1-methyl-pyrrolidin-2-one / 20 °C 2: acetic acid / 12 h / Reflux 3: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: triethylamine / 1-methyl-pyrrolidin-2-one / 20 °C 2: acetic acid / 12 h / Reflux 3: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1.1: N,N-dimethyl acetamide 2.1: acetic acid / 0.5 h / 115 °C 3.1: TEFLON / tetrahydrofuran / 0.5 h / -78 °C 3.2: 0.5 h / -78 °C View Scheme |
4-chlorobenzoyl chloride
N-phenyl-1,2-benzenediamine
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran 2: n-butyllithium View Scheme |
Trimethyl borate
2-(4-bromophenyl)-1-phenyl-1H-benzimidazole
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
Stage #1: 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole With n-butyllithium Stage #2: Trimethyl borate Stage #3: With hydrogenchloride In water |
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol; water / 10 h / 85 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C / Inert atmosphere 2.2: 12 h / 20 °C / Inert atmosphere View Scheme |
2-bromo-1H-1,3-benzodiazole
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: copper(l) iodide; 18-crown-6 ether; potassium carbonate / N,N-dimethyl acetamide / 12 h / 165 °C / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol; water / 10 h / 85 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C / Inert atmosphere 3.2: 12 h / 20 °C / Inert atmosphere View Scheme |
iodobenzene
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: copper(l) iodide; 18-crown-6 ether; potassium carbonate / N,N-dimethyl acetamide / 12 h / 165 °C / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol; water / 10 h / 85 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C / Inert atmosphere 3.2: 12 h / 20 °C / Inert atmosphere View Scheme |
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 5h; Suzuki Coupling; Inert atmosphere; Reflux; | 95% |
9-(2-chloroquinazolin-4-yl)-9H-carbazole
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; toluene at 100℃; for 4h; Inert atmosphere; | 94% |
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
2-amino-6-bromophenol
Conditions | Yield |
---|---|
With palladium diacetate; sodium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; | 92% |
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate; XPhos In ethanol; water; toluene Suzuki Coupling; | 91.7% |
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 5h; Reflux; | 91% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 12h; Reflux; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water for 5h; Reflux; Inert atmosphere; | 89% |
3,5-bis(4-tert-butylphenyl)-1-bromobenzene
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 12h; Inert atmosphere; | 89% |
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
para-bromoacetophenone
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 80℃; for 16h; Inert atmosphere; | 88.5% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 20 - 80℃; for 16h; Inert atmosphere; | 88.5% |
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 85℃; for 14h; Inert atmosphere; | 88% |
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 5h; Reflux; | 87% |
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate; XPhos In tetrahydrofuran; water for 4h; Inert atmosphere; Reflux; | 87% |
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
10-(4-Bromophenyl)-12,12-dimethyl-10,12dihydro-10-azaindeno[2,1-b]-fluorene
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate; XPhos In ethanol; water; toluene Suzuki Coupling; | 85.7% |
(rac)-2,2'-diiodo-9,9'-spirobifluorene
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
C63H40N4
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); tri-tert-butyl phosphine; sodium carbonate In toluene for 48h; Inert atmosphere; Reflux; | 85% |
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
C31H20BrN
8,8-Diphenyl-6-[4-(1-phenyl-1H-benzoimidazol-2-yl)-phenyl]-8H-indolo[3,2,1-de]acridine
Conditions | Yield |
---|---|
With potassium phosphate monohydrate; tris-(o-tolyl)phosphine; palladium diacetate In 1,4-dioxane; water; toluene for 5h; Reflux; | 85% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 5h; Inert atmosphere; Heating; | 85% |
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In tetrahydrofuran; water at 90℃; for 24h; Inert atmosphere; | 85% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 70℃; for 8h; Inert atmosphere; | 84.9% |
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
2,7-dibromo-9,9'-spirobi[fluorene]
C63H40N4
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); tri-tert-butyl phosphine; sodium carbonate In toluene for 48h; Inert atmosphere; Reflux; | 84% |
9-Bromoanthracene
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
9-[4-(1-phenyl-1H-benzimidazol-2-yl)phenyl]anthracene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 6h; Inert atmosphere; Reflux; | 83% |
Conditions | Yield |
---|---|
With potassium phosphate; bis(tri-t-butylphosphine)palladium(0) In 1,4-dioxane; water for 5h; Reflux; | 83% |
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
2-phenyl-6-chloroimidazo<1,2-b>pyridazine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 10h; Reflux; Inert atmosphere; | 83% |
Conditions | Yield |
---|---|
With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); sodium carbonate In toluene at 75 - 90℃; Inert atmosphere; | 83% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 10h; Suzuki Coupling; | 82.9% |
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 24h; Reflux; | 82% |
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate In tetrahydrofuran; water for 6h; Suzuki Coupling; Reflux; Inert atmosphere; | 82% |
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
3-bromo-9-(naphthalen-2-yl)-9H-carbazole
9-(naphthyl-2-yl)-3-(4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)-9H carbazole
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 48h; Suzuki coupling; Inert atmosphere; Reflux; | 81.2% |
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 5h; Inert atmosphere; Reflux; | 81% |
(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In methanol; water; toluene at 110℃; for 12h; Suzuki Coupling; Inert atmosphere; | 81% |
Molecular Structure of 4-(1-Phenyl-1H-benzimidazol-2-yl)phenylboronic acid (CAS No.952514-79-3):
Molecular Formula: C19H15BN2O2
Molecular Weight: 314.15
CAS No: 952514-79-3
Product Categories: Electronic Chemicals
4-(1-Phenyl-1H-benzimidazol-2-yl)phenylboronic acid (CAS No.952514-79-3), its synonym is B-[4-(1-Phenyl-1H-benzimidazol-2-yl)phenyl]boronic acid .
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