Structure of 2-Hydroxyphenylboronic acid
CAS No.: 89466-08-0
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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. : | 89466-08-0 |
Formula : | C6H7BO3 |
M.W : | 137.93 |
SMILES Code : | C1=C(C(=CC=C1)B(O)O)O |
MDL No. : | MFCD01074581 |
InChI Key : | YDMRDHQUQIVWBE-UHFFFAOYSA-N |
Pubchem ID : | 2773454 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H302-H318 |
Precautionary Statements: | P264-P270-P280-P301+P312+P330-P305+P351+P338+P310-P501 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 3.0 |
Molar Refractivity | 38.29 |
TPSA ? Topological Polar Surface Area: Calculated from |
60.69 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 |
1.02 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.93 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.36 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-1.2 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.29 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.72 |
Solubility | 2.65 mg/ml ; 0.0192 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.88 |
Solubility | 1.8 mg/ml ; 0.0131 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.68 |
Solubility | 28.6 mg/ml ; 0.207 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
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 |
-6.42 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) |
1.52 |
* 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 |
---|---|---|
96% | With potassium fluoride; palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; water; at 20℃; for 1.5h;Inert atmosphere; | B-2 (2.17 g, 10.0 mmol) and 2-hydroxybenzene boronic acid (1 .38 g, 10.0 mmol) were dissolved in 10 mL of THF. To the solution was added potassium fluoride (1.74 g, 30.0 mmol) dissolved in 5 mL of water, and the mixture was evacuated and purged with Argon gas. Then, 'Betaupsilon3Rho-EtaBetaRho4 (290 mg, 1.00 mmol) and Pd(OAc)2 (225 mg, 1.00 mmol) were added to the mixture, and the mixture was stirred at room temperature for 1 .5 h. The reaction mixture was dried with MgS04, filtrated over Celite and washed with ethyl acetate. The crude was purified by column chromatography on silica gel eluting with a mixed solvent of heptane and ethyl acetate (3:1 ) to yield 2.27 g (96%) of B-3 as a slightly yellow solid. It was used for next reaction without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 90℃; for 6h;Schlenk technique; | accurately weighed 2,3-dibromobenzo [fo] thiophene (683 mg, 2.34 mmol), 2-light benzene phenylboronic acid (484 mg, 3.5(1 · 29 g, 9.36 mmol), tetrakis (triphenylphosphine) palladium (0.05 equivalent), 1,4-dioxane Hexahedral / water (volume ratio 4: 1), placed in a 90 C oil bath for 6 hours. After completion of the reaction, the solvent was removed under reduced pressure, and silica gel column separation, petroleum ether / ethyl acetate was used as the eluent to give 2- (3-bromobenzothiazol-2-yl) phenol 3a in 84% yield. |
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