Structure of 1,4-Phenylenediboronic acid
CAS No.: 4612-26-4
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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| CAS No. : | 4612-26-4 |
| Formula : | C6H8B2O4 |
| M.W : | 165.75 |
| SMILES Code : | C1=CC(=CC=C1B(O)O)B(O)O |
| MDL No. : | MFCD00236018 |
| InChI Key : | BODYVHJTUHHINQ-UHFFFAOYSA-N |
| Pubchem ID : | 230478 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H302 |
| Precautionary Statements: | P264-P270-P301+P312-P501 |
| Num. heavy atoms | 12 |
| Num. arom. heavy atoms | 6 |
| Fraction Csp3 | 0.0 |
| Num. rotatable bonds | 2 |
| Num. H-bond acceptors | 4.0 |
| Num. H-bond donors | 4.0 |
| Molar Refractivity | 46.09 |
| TPSA ? Topological Polar Surface Area: Calculated from |
80.92 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.0 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.27 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-2.95 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-1.47 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-3.26 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-1.59 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-0.94 |
| Solubility | 19.2 mg/ml ; 0.116 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-0.97 |
| Solubility | 17.7 mg/ml ; 0.107 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.17 |
| Solubility | 112.0 mg/ml ; 0.675 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
| BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
| P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
| CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
| CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
| CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
| CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
| CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
Yes |
| Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-7.5 cm/s |
| Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
| Ghose? Ghose filter: implemented from |
None |
| Veber? Veber (GSK) filter: implemented from |
0.0 |
| Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
| Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
| Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
| PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
| Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
| Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
| Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.96 |
* 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.

[ 104-92-7 ]
[ 4612-26-4 ]
[ 104197-14-0 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 45% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In methanol; water; for 12h;Reflux; Inert atmosphere; | 1,4-Phenylene diboronic acid (1.0 g, 6.03 mmol) was dissolved in 1,2-dimethoxyethanol (100 mL) and methanol (10 mL)4-Bromoanisole (1.24 g, 6.64 mmol) and <strong>[104197-14-0]2,6-difluoro-4-bromoanisole</strong> (1.48 g, 6.64 mmol) were added dropwise to the above mixed solution,2 M aqueous potassium carbonate solution (20 mL) was added and degassed. Palladium tetrakis (triphenylphosphine) (349 mg, 0.30 mmol) was added to the mixed solution, and the mixture was refluxed under nitrogen atmosphere for 12 hours.An excessive amount of distilled water was added to the reaction solution to terminate the reaction,After extracting with dichloromethane, the solvent was concentrated under reduced pressure. The mixture obtained above was purified by column chromatography to give the desired compound (913 mg, 45%) as a white solid. |
[ 104-92-7 ]
[ 406482-22-2 ]
[ 4612-26-4 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 42% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In methanol; water; for 12h;Reflux; Inert atmosphere; | 1,4-phenylene diboronic acid (1.0 g, 6.03 mmol)1,2-Dimethoxyethanol (100 mL)And methanol (10 mL) was addedAfter dissolution,4-Bromoanisole (1.24 g, 6.64 mmol) and <strong>[406482-22-2]2,3-difluoro-4-bromoanisole</strong> (1.48 g, 6.64 mmol) were added dropwise to the mixed solution,2 M aqueous potassium carbonate solution (20 mL) was added and degassed.To the mixed solution, palladium tetrakis (triphenylphosphine)(349 mg, 0.30 mmol), and the mixture was refluxed under nitrogen atmosphere for 12 hours.An excessive amount of distilled water was added to the reaction solution to terminate the reaction,After extraction with dichloromethane, the solvent was concentrated under reduced pressure,The residue was purified by column chromatography to give the desired compound (827 mg, 42%) as a white solid. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 75.3% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; at 85℃; for 24h;Inert atmosphere; | Bromo-2,4,5-trimethyl-benzene (1) (2.64 g, 13.26 mmol), benezene- 1 ,4-diboronic acid (3) (1.00 g, 6.03 mmol) and a catalytic amount of tetrakis(triphenylphosphine)palladium(0) (0.10 g, 0.08 mmol) were added into a two-necked flask fitted with an Allihn condenser. The system was degassed and refilled with nitrogen three times. Then, 60 mL of distilled THF was injected, followed with an aqueous solution of potassium carbonate (0.15 g, 20 mL). After stifling at 85 C for 24 h, the mixture was extracted with DCM. The organic layer was collected and washed with deionized water and brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was evaporated under reduced pressure, and the crude product was purified by silica gel column chromatography using hexanelDCM (5/1, v/v) as eluent. A white powder of TPh-TM was obtained in 75.3% yield (1.42 g, 4.52 mmol). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; for 24h;Inert atmosphere; Resolution of racemate; | (i) Combine 1,4-biphenylboronic acid (1.04g, 6.30mmol) and <strong>[54151-74-5]2-bromo-4-phenylpyridine</strong> (4.42g, 18.9mmol), K2CO3 (1.80g, 13.0mmol), tetrakis(triphenyl) Phosphine) Palladium (1.31g, 1.13mmol) dissolvedIn 1,4-dioxane (50.0 mL). The mixture was refluxed under N2 for 24 hours. After the reaction mixture was cooled to room temperature and all solvents were removed by rotary evaporation, it was extracted with dichloromethane, washed with water, dried over magnesium sulfate, filtered, and evaporated to dryness. The crude product was purified by silica gel column chromatography to obtain compound III as a white solid. |

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