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CAS No. : | 1084334-86-0 | MDL No. : | MFCD28144504 |
Formula : | C24H20BNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UUOYDHJVGOATFJ-UHFFFAOYSA-N |
M.W : | 365.23 | Pubchem ID : | 57746617 |
Synonyms : |
|
Num. heavy atoms : | 28 |
Num. arom. heavy atoms : | 24 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 116.39 |
TPSA : | 43.7 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.49 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 5.69 |
Log Po/w (WLOGP) : | 4.5 |
Log Po/w (MLOGP) : | 4.2 |
Log Po/w (SILICOS-IT) : | 2.66 |
Consensus Log Po/w : | 3.41 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.99 |
Solubility : | 0.000371 mg/ml ; 0.00000102 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -6.37 |
Solubility : | 0.000155 mg/ml ; 0.000000423 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -8.12 |
Solubility : | 0.00000274 mg/ml ; 0.0000000075 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.82 |
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 |
---|---|---|
73% | Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at 20℃; for 4 h; |
2-2. Preparation of compound 10[173]N-(4-bromophenyl)-N-phenyl-[1,1’-biphenyl]-4-amine (15.0 g, 37.5 mmol) was dissolved in tetrahydrofurane (190.0 mL) and n-butyl lithium (2.5 M in hexane) (22.0 mL) was added to the mixture at -78 . The mixture was stirred for 1 hour and trimethoxyborane (6.3 mL, 56.21 mmol) was added thereto. After stirring the whole mixture for 4 hours at room temperature, the mixture was extracted with ethyl acetate (200.0 mL) and the obtained organic layer was washed with distilled water (100.0 mL). The organic solvent was removed under the reduced pressure. The obtained solid was washed with hexane, filtered and dried to obtain (4-([1,1-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid (10.0 g, 73percent). |
61% | Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h; Inert atmosphere Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 25 h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane at 20℃; for 1 h; |
(iii) Synthesis of 4-[N-(biphenyl-4-yl)-N-phenylamino]phenylboronic acid A synthesis scheme (C-4) of 4-[N-(biphenyl-4-yl)-N-phenylamino]phenylboronic acid is shown below. In a 300-mL three-neck flask, 7.0 g (18 mmol) of 4-bromo-4'-phenyltriphenylamine was put, and the atmosphere in the flask was substituted by nitrogen. Then, 80 mL of tetrahydrofuran (abbreviation: THF) was added thereto, and the mixture was stirred at -78° C. for 10 minutes. After that, 13 mL (21 mmol) of an n-butyllithium hexane solution (1.63 mol/L) was dropped into this solution from a syringe, and the solution was stirred at -78° C. for 1 hour. After a certain time, 3.5 mL of trimethyl borate was added to the reaction mixture and the mixture was stirred at -78° C. for 1 hour, then stirred for 24 hours while changing the temperature from -78° C. to room temperature. After stirring, 100 mL of 1M dilute hydrochloric acid was added to the solution, and the mixture was stirred at room temperature for 1 hour. After stirring, ethyl acetate was added to this solution for extraction. After extraction, the extract was washed with a saturated saline. After washing, magnesium sulfate was added to the extract for drying. After the drying, magnesium sulfate was removed by suction filtration to give a filtrate. The obtained filtrate was concentrated and recrystallized from a mixed solvent of chloroform and hexane to give 4.0 g of the target substance, 4-[N-(biphenyl-4-yl)-N-phenylamino]phenylboronic acid in a yield of 61percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h; Stage #2: at -78 - 20℃; for 25 h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane at 20℃; for 1 h; |
Step 1: Synthesis of 4-[λT-(biphenyl-4-yl)-λT-phenyl]aminophenylboronic acid][0410]A synthetic scheme of 4-[N-(biphenyl-4-yl)-λT-phenyl]aminophenylboronic acid in Step 1 is shown in the following (η-l). [0411] <n="176"/>[0412]In a 300-mL three-neck flask, 7.0 g (18 mmol) of 4-bromo-4'-phenyltriphenylamine was put, and the atmosphere in the flask was substituted by nitrogen. Then, 80 mL of tetrahydrofuran (abbreviation: THF) was added thereto, and the mixture was stirred at -780C for 10 minutes. After that, 13 mL (21 mmol) of an n-butyllithium hexane solution (1.63 mol/L) was dropped onto this solution from a syringe, and the solution was stirred at -780C for 1 hour. After the stirring, 3.5 mL (31 mmol) of trimethyl borate was added to the reaction mixture, and the mixture was stirred at -78 0C for 1 hour and at room temperature for 24 hours. After the reaction, 100 mL of IM dilute hydrochloric acid was added to the reaction solution, and the mixture was stirred at room temperature for 1 hour. After the stirring, this solution was extracted with ethyl acetate, and an organic layer was washed with a saturated saline solution. After the washing, magnesium sulfate was added to the organic layer, and the organic layer was dried. After the drying, magnesium sulfate was removed by suction filtration to obtain filtrate. The obtained filtrate was concentrated and recrystallized with a mixture solvent of chloroform and hexane to obtain 3.6 g of an object at a yield of 56 percent. |
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