Conditions | Yield |
---|---|
Stage #1: 4-bromodibenzofuran With n-butyllithium In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran at 20℃; for 8h; | 94% |
Stage #1: 4-bromodibenzofuran With n-butyllithium In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran at 20℃; for 8h; |
dibenzofuran
Trimethyl borate
water
4-dibenzofurylboronic acid
Conditions | Yield |
---|---|
Stage #1: dibenzofuran With n-butyllithium In tetrahydrofuran; hexane; acetone at -60 - 20℃; for 5h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane; acetone at -45 - 20℃; for 15h; Inert atmosphere; Stage #3: water With hydrogenchloride In tetrahydrofuran; hexane; acetone at 10 - 20℃; for 4h; Inert atmosphere; | 93.8% |
Stage #1: dibenzofuran With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 12.5h; Stage #3: water With hydrogenchloride In tetrahydrofuran; hexane at 0℃; | 69.3% |
dibenzofuran
bis(diisopropylamino)chloroborane
water
4-dibenzofurylboronic acid
Conditions | Yield |
---|---|
Stage #1: dibenzofuran With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane for 2h; Inert atmosphere; Reflux; Stage #2: bis(diisopropylamino)chloroborane In hexane at 0℃; Inert atmosphere; Stage #3: water With hydrogenchloride at 10℃; pH=2 - 3; | 88% |
dibenzofuran
bromobis(dimethylamino)borane
water
4-dibenzofurylboronic acid
Conditions | Yield |
---|---|
Stage #1: dibenzofuran With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane for 2h; Inert atmosphere; Reflux; Stage #2: bromobis(dimethylamino)borane In hexane at -10℃; for 3h; Inert atmosphere; Stage #3: water With hydrogenchloride at -10 - 10℃; pH=2 - 3; | 82% |
Conditions | Yield |
---|---|
Stage #1: 4-bromodibenzofuran With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water at 20℃; for 3h; | 80% |
Stage #1: 4-bromodibenzofuran With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 1h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at -78℃; Stage #3: With hydrogenchloride In tetrahydrofuran; water for 0.5h; | 73% |
Stage #1: 4-bromodibenzofuran With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 1h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at -78℃; for 12h; Stage #3: With hydrogenchloride; water In tetrahydrofuran for 0.5h; | 73% |
Stage #1: 4-bromodibenzofuran With n-butyllithium In tetrahydrofuran for 1h; Stage #2: Trimethyl borate In tetrahydrofuran at 20℃; | 70% |
Stage #1: 4-bromodibenzofuran With n-butyllithium In tetrahydrofuran for 2h; Cooling with acetone-dry ice; Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 0℃; for 1h; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 0 - 20℃; for 8h; |
dibenzofuran
chloro-bis(dimethylamino)borane
water
4-dibenzofurylboronic acid
Conditions | Yield |
---|---|
Stage #1: dibenzofuran With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane for 2h; Inert atmosphere; Reflux; Stage #2: chloro-bis(dimethylamino)borane In hexane at -10℃; Inert atmosphere; Stage #3: water With hydrogenchloride at 10℃; pH=2 - 3; | 77% |
Conditions | Yield |
---|---|
Stage #1: dibenzofuran With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; | 48.5% |
Conditions | Yield |
---|---|
Stage #1: dibenzofuran With n-butyllithium In tetrahydrofuran; hexane at -68 - -20℃; for 1h; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at -68 - 20℃; for 5h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water; ethyl acetate |
dibenzofuran
4-dibenzofurylboronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 6 h / -78 - 0 °C / Inert atmosphere 1.2: 10 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran / 2 h / Cooling with acetone-dry ice 2.2: 1 h / -78 - 0 °C 2.3: 8 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 2.5 h / -40 - 20 °C / Inert atmosphere 1.2: 2.5 h / -78 - 20 °C 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 2.2: -78 °C 2.3: 0.5 h View Scheme | |
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 2.5 h / -40 - 20 °C / Inert atmosphere 1.2: 2.5 h / -78 - 20 °C 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 2.2: 12 h / -78 °C 2.3: 0.5 h View Scheme |
Conditions | Yield |
---|---|
With copper(I) iodide-lithium chloride In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere; |
4-bromodibenzofuran
Triisopropyl borate
water
4-dibenzofurylboronic acid
Conditions | Yield |
---|---|
Stage #1: 4-bromodibenzofuran With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran at -78 - 20℃; for 0.5h; Stage #3: water With hydrogenchloride In tetrahydrofuran |
4-dibenzofurylboronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate; tetrabutyl-ammonium chloride / water; toluene; ethanol / 12 h / 78 °C / Inert atmosphere 2.1: boron tribromide / dichloromethane / 3.33 h / 20 °C / Inert atmosphere 3.1: sodium hydroxide / 1-methyl-pyrrolidin-2-one / 3 h / Reflux 4.1: n-butyllithium / tetrahydrofuran / 1 h 4.2: 20 °C View Scheme |
2-Methoxyphenylboronic acid
4-dibenzofurylboronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate; tetrabutyl-ammonium chloride / water; toluene; ethanol / 12 h / 78 °C / Inert atmosphere 2.1: boron tribromide / dichloromethane / 3.33 h / 20 °C / Inert atmosphere 3.1: sodium hydroxide / 1-methyl-pyrrolidin-2-one / 3 h / Reflux 4.1: n-butyllithium / tetrahydrofuran / 1 h 4.2: 20 °C View Scheme |
4-dibenzofurylboronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: boron tribromide / dichloromethane / 3.33 h / 20 °C / Inert atmosphere 2.1: sodium hydroxide / 1-methyl-pyrrolidin-2-one / 3 h / Reflux 3.1: n-butyllithium / tetrahydrofuran / 1 h 3.2: 20 °C View Scheme |
4-dibenzofurylboronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium hydroxide / 1-methyl-pyrrolidin-2-one / 3 h / Reflux 2.1: n-butyllithium / tetrahydrofuran / 1 h 2.2: 20 °C View Scheme |
Conditions | Yield |
---|---|
With tetra-butylammonium acetate; Pd EnCat-30TM In ethanol at 120℃; for 0.166667h; Suzuki cross-coupling; microwave irradiation; | 100% |
4-dibenzofurylboronic acid
3,5-Dichloroaniline
Glyoxilic acid
(dibenzofuran-4-yl)-(3,5-dichlorophenylamino)acetic acid
Conditions | Yield |
---|---|
In dichloromethane at 20℃; | 100% |
4-dibenzofurylboronic acid
2-nitrophenyl bromide
4-(2-nitrophenyl)dibenzo[b,d]furan
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene for 12h; Reflux; | 100% |
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene for 24h; Reflux; | 99.7% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 3h; Reflux; | 98% |
4-dibenzofurylboronic acid
2-(carboxymethyl)-4-iodobenzoic acid
2-(carboxymethyl)-4-(dibenzo[b,d]furan-4-yl)benzoic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water at 150℃; for 0.5h; Suzuki coupling; Inert atmosphere; Microwave irradiation; | 100% |
2-Chloro-3-nitropyridine
4-dibenzofurylboronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene Inert atmosphere; Reflux; | 100% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 6h; Inert atmosphere; Reflux; | 84% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 6h; Suzuki Coupling; Reflux; Inert atmosphere; | 84% |
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl acetamide at 80℃; for 3.5h; Suzuki-Miyaura Coupling; Inert atmosphere; chemoselective reaction; | 100% |
benzoimidazole
4-dibenzofurylboronic acid
Conditions | Yield |
---|---|
With copper(I) oxide In methanol at 20℃; | 98% |
4-dibenzofurylboronic acid
C10H9IO3
5-(dibenzo[b,d]furan-4-yl)-2,2-dimethyl-4H-benzo[d][1,3]-dioxin-4-one
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,2-dimethoxyethane; water at 110℃; for 0.0666667h; Suzuki Coupling; Inert atmosphere; Microwave irradiation; | 98% |
4-dibenzofurylboronic acid
2-bromoaniline
2-(dibenzo[b,d]furan-4-yl)aniline
Conditions | Yield |
---|---|
Stage #1: 4-dibenzofurylboronic acid; 2-bromoaniline With potassium carbonate In 1,2-dimethoxyethane; water at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: With dichlorobis(tri-O-tolylphosphine)palladium In 1,2-dimethoxyethane; water at 80℃; for 12h; Inert atmosphere; Schlenk technique; | 98% |
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 120℃; for 3h; | 88% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 5h; Reflux; | 65% |
p-nitrobenzene iodide
4-dibenzofurylboronic acid
Conditions | Yield |
---|---|
With sodium phosphate; palladium on activated charcoal In water; isopropyl alcohol at 80℃; for 1h; Suzuki-Miyaura coupling reaction; | 97% |
With sodium phosphate dodecahydrate; palladium 10% on activated carbon In water; isopropyl alcohol at 80℃; for 1h; hetero-Suzuki-Miyaura cross-coupling; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 120℃; for 2h; | 97% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 90℃; for 24h; Inert atmosphere; | 65.49% |
3-bromo-9-phenyl-9H-carbazole
4-dibenzofurylboronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 16h; Suzuki Coupling; Reflux; | 97% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 16h; Suzuki Coupling; Reflux; | 97% |
In ethanol; water; toluene |
4-dibenzofurylboronic acid
3-bromo-N-phenyl-6-phenylcarbazole
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 16h; Suzuki Coupling; Reflux; | 97% |
bromochlorobenzene
4-dibenzofurylboronic acid
Conditions | Yield |
---|---|
With potassium carbonate In water; toluene at 90℃; for 2h; Suzuki-Miyaura Coupling; chemoselective reaction; | 97% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 80℃; for 15h; Inert atmosphere; | 80% |
benzoic acid phenyl ester
4-dibenzofurylboronic acid
dibenzo[b,d]furan-4-yl(phenyl)methanone
Conditions | Yield |
---|---|
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; water; potassium carbonate In tetrahydrofuran at 23℃; for 18h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere; | 97% |
4-dibenzofurylboronic acid
Conditions | Yield |
---|---|
With palladium diacetate; caesium carbonate; tricyclohexylphosphine In tetrahydrofuran; water; toluene at 80℃; Suzuki-Miyaura Coupling; Schlenk technique; | 97% |
[3-(bromo-phenyl)-thiazol-4-yl]-methanol
4-dibenzofurylboronic acid
[2-(3-dibenzofuran-4-yl-phenyl)-thiazol-4-yl]methanol
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 90℃; for 8h; | 96% |
4-dibenzofurylboronic acid
1-bromo-4-(trimethylsilyl)benzene
(4-dibenzofuran-4-yl-phenyl)-trimethyl-silane
Conditions | Yield |
---|---|
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 80℃; for 4h; | 96% |
Stage #1: 4-dibenzofurylboronic acid; 1-bromo-4-(trimethylsilyl)benzene With potassium carbonate In ethanol; water; toluene for 0.0833333h; Stage #2: tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 80℃; for 4h; | 96% |
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 80℃; for 4h; | 96% |
4-dibenzofurylboronic acid
para-bromoacetophenone
1-[4-(dibenzo[b,d]furan-4-yl)phenyl]ethanone
Conditions | Yield |
---|---|
With sodium phosphate; palladium on activated charcoal In water; isopropyl alcohol at 80℃; for 1h; Suzuki-Miyaura coupling reaction; | 96% |
With sodium phosphate dodecahydrate; palladium 10% on activated carbon In water; isopropyl alcohol at 80℃; for 1h; hetero-Suzuki-Miyaura cross-coupling; Inert atmosphere; | 96% |
With [Pd(N-(3-chloro-2-quinoxalinyl)-N'-(2,6-diisopropylphenyl)imidazolium)(PPh3)Cl2]; potassium carbonate In water at 70℃; for 3h; Catalytic behavior; Suzuki-Miyaura Coupling; | 88% |
With disodium[(N,N’-bis(2-hydroxy-5-sulfonatobenzyl)-1,2-diphenyl-1,2-diaminoethano)palladate(II)]; caesium carbonate In water at 80℃; for 1h; Suzuki-Miyaura Coupling; |
4-dibenzofurylboronic acid
3-bromo-5,5-dimethlycyclohex-2-en-1-one
3-dibenzofuran-4-yl-5,5-dimethyl-cyclohex-2-enone
Conditions | Yield |
---|---|
With potassium carbonate In ethanol; water at 110℃; for 0.0833333h; Suzuki coupling; Microwave irradiation; | 96% |
96% |
4-dibenzofurylboronic acid
dihydrogen peroxide
4-hydroxydibenzofuran
Conditions | Yield |
---|---|
With ammonium bicarbonate In water at 20℃; for 2h; Schlenk technique; | 96% |
The Dibenzofuran-4-boronic acid with CAS registry number of 100124-06-9 is also known as Boronic acid,B-4-dibenzofuranyl-. The IUPAC name is Dibenzofuran-4-ylboronic acid. It belongs to product categories of Heterocyclic Compounds; Boronic Acid; Dibenzofuran; Organoborons; Boronic Acids; Boronic Acids and Derivatives; Heteroaryl. In addition, the formula is C12H9BO3 and the molecular weight is 212.01. This chemical is a off-white to beige powder and should be sealed in cool, dry place away from oxidants.
Physical properties about Dibenzofuran-4-boronic acid are: (1)ACD/LogP: 3.34; (2)ACD/LogD (pH 5.5): 3.336; (3)ACD/LogD (pH 7.4): 3.247; (4)ACD/BCF (pH 5.5): 201.81; (5)ACD/BCF (pH 7.4): 164.569; (6)ACD/KOC (pH 5.5): 1552.849; (7)ACD/KOC (pH 7.4): 1266.295; (8)#H bond acceptors: 3; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.701; (12)Molar Refractivity: 60.886 cm3; (13)Molar Volume: 157.378 cm3; (14)Surface Tension: 59.311 dyne/cm; (15)Density: 1.347 g/cm3; (16)Flash Point: 218.968 °C; (17)Enthalpy of Vaporization: 73.278 kJ/mol; (18)Boiling Point: 438.451 °C at 760 mmHg; (19)Vapour Pressure: 0 mmHg at 25 °C.
When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. During using it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
1. Canonical SMILES: B(C1=C2C(=CC=C1)C3=CC=CC=C3O2)(O)O
2. InChI: InChI=1S/C12H9BO3/c14-13(15)10-6-3-5-9-8-4-1-2-7-11(8)16-12(9)10/h1-7,14-15H
3. InChIKey: ZXHUJRZYLRVVNP-UHFFFAOYSA-N
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