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CAS No.: | 5122-95-2 |
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Name: | Biphenyl-3-boronic acid |
Article Data: | 12 |
Molecular Structure: | |
Formula: | C12H11BO2 |
Molecular Weight: | 198.029 |
Synonyms: | Biphenyl-3-bronic acid;biphenyl-3-ylboronic acid;3-Biphenylboronic acid; |
EINECS: | -0 |
Density: | 1.18 g/cm3 |
Melting Point: | 193-198 °C(lit.) |
Boiling Point: | 411 °C at 760 mmHg |
Flash Point: | 202.3 °C |
Solubility: | Insoluble in water. |
Appearance: | yellow crystal powder |
Hazard Symbols: | Xi,C |
Risk Codes: | 36/37/38 |
Safety: | 37/39-26 |
PSA: | 40.46000 |
LogP: | 1.03340 |
Conditions | Yield |
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Stage #1: 3-bromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran at 20℃; for 2h; Further stages.; | 75% |
With hydrogenchloride; n-butyllithium In tetrahydrofuran soln. of n-BuLi in hexanes added dropwise to soln. of biphenyl compd. at-78°C under Ar, kept at this temp. for 2 h, soln. of borate adde d over 30 min, allowed to warm to room temp. overnight, 10% aq. HCl added, stirred for 2 h at room temp.; extd. into Et2O, washed with concd. soln. of Na2CO3 then with H2O, evapd., recrystd. twice from H2O/EtOH (95/5); | 75% |
Stage #1: 3-bromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane for 24h; | 65% |
With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane BuLi soln. (hexane) addn. to biphenylbromide soln. (THF), mixt. stirring1 h, mixt. addn. to B-compd. soln. (THF) via canula (N2) at -78° C., stirring 1 h, gradual warming to room temp., aq. HCl addn., stirringat room temp. 15 h, solvent removal; under reduced pressure, Et2O addn., org. layer sepn., drying (MgSO4), soln. concn.. oil triturating with hexane, solid repptn. from MeOH/H2O; | 43% |
With hydrogenchloride; tert.-butyl lithium In water; pentane |
Conditions | Yield |
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Stage #1: 3-bromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -80℃; for 1h; Inert atmosphere; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -80 - 20℃; for 4h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane for 2h; | 55% |
Multi-step reaction with 2 steps 1.1: n-BuLi / -78 °C 1.2: -78 - 20 °C 2.1: aq. HCl View Scheme | |
Stage #1: 3-bromobiphenyl With magnesium In tetrahydrofuran Stage #2: With Trimethyl borate Stage #3: With hydrogenchloride Further stages.; |
Conditions | Yield |
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With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane BuLi soln. (hexane) addn. to biphenylbromide soln. (THF), mixt. stirring1 h, mixt. addn. to B-compd. soln. (THF) via canula (N2) at -78° C., stirring 1 h, gradual warming to room temp., aq. HCl addn., stirringat room temp. 15 h, solvent removal; under reduced pressure, Et2O addn., org. layer sepn., drying (MgSO4), soln. concn.. oil triturating with hexane, solid repptn. from MeOH/H2O; | 40% |
boric acid tributyl ester
[(1,1'-biphenyl)-3-yl]magnesium bromide
3-Biphenylboronic acid
Conditions | Yield |
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With diethyl ether at -70℃; und anschliessenden Hydrolyse; |
3-Biphenylboronic acid
Conditions | Yield |
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With hydrogenchloride |
Conditions | Yield |
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Multi-step reaction with 3 steps 1.1: Pd(PPh3)4; Na2CO3 / 1,2-dimethoxy-ethane / 80 °C 2.1: n-BuLi / -78 °C 2.2: -78 - 20 °C 3.1: aq. HCl View Scheme | |
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol / 3 h / 90 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 2.2: 24 h View Scheme |
Conditions | Yield |
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Multi-step reaction with 3 steps 1.1: Pd(PPh3)4; Na2CO3 / 1,2-dimethoxy-ethane / 80 °C 2.1: n-BuLi / -78 °C 2.2: -78 - 20 °C 3.1: aq. HCl View Scheme |
Conditions | Yield |
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Stage #1: 3-bromobiphenyl With n-butyllithium In diethyl ether; hexane; toluene at -30 - 0℃; for 1h; Stage #2: Triisopropyl borate In diethyl ether; hexane; toluene at -70 - 20℃; for 1h; Stage #3: With hydrogenchloride; water In diethyl ether; hexane; toluene | |
With tert.-butyl lithium In diethyl ether; pentane |
Conditions | Yield |
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Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol / 3 h / 90 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 2.2: 24 h View Scheme |
9-bromo-N-(tert-butyl)-3,4-dihydro-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine
3-Biphenylboronic acid
9-[(1-1’-biphenyl)-3-yl]-N-(tert-butyl)-3,4-dihydro-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine
Conditions | Yield |
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With tetrakis(triphenylphosphine) palladium(0); dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In ethanol; water; toluene for 1h; Suzuki-Miyaura Coupling; Reflux; | 100% |
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(1):Handling and Storage of 3-BIPHENYLBORONIC ACID
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Store in a tightly closed container. Store in a dry area. Keep refrigerated(Store below 4°C/39°F.)
(2):Fire Fighting Measures of 3-BIPHENYLBORONIC ACID
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.