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CAS No. : | 5122-94-1 | MDL No. : | MFCD00093311 |
Formula : | C12H11BO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XPEIJWZLPWNNOK-UHFFFAOYSA-N |
M.W : | 198.03 | Pubchem ID : | 151253 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 61.7 |
TPSA : | 40.46 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.77 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 2.45 |
Log Po/w (WLOGP) : | 1.03 |
Log Po/w (MLOGP) : | 1.88 |
Log Po/w (SILICOS-IT) : | 0.9 |
Consensus Log Po/w : | 1.25 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.07 |
Solubility : | 0.168 mg/ml ; 0.000849 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.94 |
Solubility : | 0.226 mg/ml ; 0.00114 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.81 |
Solubility : | 0.0307 mg/ml ; 0.000155 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.92 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5 h; Inert atmosphere Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 4.5 h; Stage #3: With water In tetrahydrofuran; hexane; ethyl acetate |
4-bromobiphenyl (30g, 0.12mop was added to a one-neck flask and an argon atmosphere was established in a vacuum. Tetrahydinfuran (THA) (SOOmI) was added and the mixture was stirred at -7KC for 10 minutes. After adding mBuLi(2.SM in hexane) (77mL, 0.19moL), the mixture was stiu-a3 for I hour and 30 minutes at -7RC. Then, nimethyl borate (21.9m1, 0. 9mol) was added at-78C After sorting the mixture for 30 minutes at-78C, the mixture was stirred at room temperature for 4 hours. After the reaction was completed, extraction was performed using distilled water and ethyl acetate (EA). The organic layer was dried with MgSO, and the solvent was removed using a rotary evaporator. Pure Compound A (21g 84percent) was separated by column chromatography using hexane and EA as an eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | Stage #1: With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5 h; Stage #2: at -78 - 20℃; |
Sub 2-1 (4) (4.66g, 20mmol) dissolved in anhydrous Ether, a reaction temperature of-78 ° C to a lower, n-BuLi (2.5M in hexane) (1.4g, 22mmol) was slowly addeddropwise, and I then, the reaction is stirred for 30 minutes. After the dropwise additionTriisopropyl borate (5.64g, 30mmol) lowering the temperature of the reaction back to -78 ° C. Stirring at room temperature, diluted with water and it binds the 2N HCl. Aftercompletion of reaction, ethyl acetate and water, dried over MgSO4 and the organic layerwas extracted and concentrated and to the resulting organic silicagel column andrecrystallized to give 2.93g of Sub 2 (4). (Yield: 74percent) |
90% | With n-butyllithium In tetrahydrofuran | To a solution of 4-bromobiphenyl (2.00 g, 8.58 mmol) in THF (20 mL) at -78° C. was added n-butyllithium (4.0 mL of 2.5 M in hexanes) in a slow stream via syringe. After 15 minutes, triisopropylborate (3.0 mL, 13 mmol) was added in a slow stream via syringe. After 10 minutes, the resultant homogeneous solution was allowed to warm to ambient temperature over 45 minutes and partitioned between EtOAc (50 mL) and 10percent aqueous HCI (50 mL). The aqueous layer was separated and extracted with more EtOAc. The combined organic layers were washed with brine, dried over Na2 SO4 and concentrated to give a crude product which was triturated with hexanes to yield 1.53 g (90percent) of 4-biphenylboronic acid as a white solid. 1 H NMR (DMSO-d6): δ 8.05 (s, 2H), 7.83 (d, 2H, J=8.5 Hz), 7.65 (d, 2H, J=7.0 Hz), 7.60 (d, 2H, J=8.1 Hz), 7.43 (t, 2H, J=7.4 Hz), 7.33 (t, 1H, J=7.2 Hz). Anal. C12 H11 BO2: C, 72.78; H, 560. Found: C, 72.51; H, 5.62. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With potassium carbonate In ethanol; water at 50℃; for 5 h; Inert atmosphere | Under a nitrogen gas atmosphere, Phenylboronic acid150 mg (1.23 mmol)324 mg (0.55 mmol) of potassium salt of stable art type complex of 4-bromophenylboronic acid and scyllo-inositol (0.55 mmol) of potassium salt of scyllo-inositol and 340 mg (2.46 mmol) of potassium carbonate were dissolved in degassed ethanol: 1) mixed solvent, and a catalyst solution prepared by suspending 8 mg (0.012 mmol) of triphenylphosphine ligand-palladium in 1 mL of a mixed solvent of ethanol: water (5: 1) was added thereto , And the cross-coupling reaction was started by stirring at a reaction temperature of 50 ° C. After 5 hours of reaction, the reaction solvent was distilled off under reduced pressure to stop the reaction. 15 ml of water and 10 ml of ethyl acetate were added to the residue and dissolved / extracted, and the obtained suspension was filtered to remove the insoluble catalyst. Further, an ethyl acetate layer and an aqueous layer were separated, and the aqueous layer was further washed with a small amount of ethyl acetate. The aqueous layer was taken out and hydrochloric acid was added so that the pH became 2 to 3, the scyllo-inositol complex dissociated and the deprotection reaction progressed. The arylboronic acid was insolubilized with deprotection in an acidic aqueous solution. Thereto, 15 ml of ethyl acetate was added to extract the arylboronic acid, and the mixture was separated to obtain an ethyl acetate layer. The aqueous layer was again extracted with 10 ml of ethyl acetate, combined with the first ethyl acetate solution, dried with anhydrous Na 2 SO 4 and concentrated. The precipitated solid was purified by silica gel column chromatography to obtain 187 mg (0.95 mmol) of biphenyl 4-boronic acid (yield: 86percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: With magnesium; phenylmagnesium bromide In tetrahydrofuran at 20℃; for 0.166667 h; Stage #2: at 70℃; |
General procedure: To a solution in THF (4 mL) of DIPAB (863 mg, 7.5 mmol) and Mg (182 mg, 7.5 mmol) were added a PhMgBr 1M THF solution (375 μL, 375μmol) at room temperature. After 10 min, 30 mL of anhydrous THF were added followed by the arylbromide (5 mmol). The reaction mixture was cooled down to 0 °C and quenched slowly with 7 mL of MeOH. After 1h, volatile were removed under reduced pressure and the resulting solid was dissolved in 1N HCl/MeOH (7/3). After 1h at room temperature, 100 mL of AcOEt were added, the organic phase was washed with 1N HCl (30 mL) and brine (3×30 mL). Organic phases were concentrated under reduced pressure yielding a solid which was recrystallized from H2O. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.82 g | With hydrogenchloride In tetrahydrofuran for 0.5 h; Inert atmosphere | Under nitrogen, 2.33 g (10 mmol) of 4-bromo-1,1'-biphenyl was dissolved in 40 ml of anhydrous THF, the temperature of the reaction was lowered to -78 ° C, After slowly adding 4 ml of 2.5 M n-BuLi dropwise, the reaction was stirred at 0 ° C for 1 hour. Then, the temperature of the reaction After lowering to -78 deg. C, 12.47 g (12 mmol) of trimethylborate was added dropwise, and the mixture was stirred at room temperature for 12 hours. The reaction After completion of the reaction, 2N-HCl aqueous solution was added, stirred for 30 minutes, and extracted with ether. Water in the organic layer was removed with anhydrous MgSO 4, filtered under reduced pressure, and the organic solvent was concentrated to obtain the resulting compound in a ratio of Hex: MC = 6: 1 to obtain 1.82 g (92percent) of |
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