Structure of 18982-54-2
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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. : | 18982-54-2 |
Formula : | C7H7BrO |
M.W : | 187.03 |
SMILES Code : | C1=CC=CC(=C1CO)Br |
MDL No. : | MFCD00004600 |
InChI Key : | IOWGHQGLUMEZKG-UHFFFAOYSA-N |
Pubchem ID : | 72850 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H412 |
Precautionary Statements: | P273 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 40.27 |
TPSA ? Topological Polar Surface Area: Calculated from |
20.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.76 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.23 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.79 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.3 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.37 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.89 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.2 |
Solubility | 1.18 mg/ml ; 0.00628 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.25 |
Solubility | 10.5 mg/ml ; 0.0559 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.08 |
Solubility | 0.156 mg/ml ; 0.000832 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 |
Yes |
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) |
Yes |
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) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.57 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 |
2.0 |
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 |
0.0 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) |
1.0 |
* 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 |
---|---|---|
153 mg (83%) | With potassium fluoride;palladium diacetate; In tetrahydrofuran; | EXAMPLE 35 Synthesis of 2-hydroxymethylbiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 2-bromobenzyl alcohol (187 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 153 mg (83percent) of the title compound. |
153 mg (83%) | With potassium fluoride;palladium diacetate; In tetrahydrofuran; | Example 35 Synthesis of 2-hydroxymethylbiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 2-bromobenzyl alcohol (187 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered througth celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 153 mg (83percent) of the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | In N,N-dimethyl-formamide; mineral oil; | (a) 3-(o-Bromobenzyloxy)4-methoxybenzonitrile To a solution of 2-bromobenzyl alcohol (16.50 g, 88.2 mmol) in DMF (100 ml) was added sodium hydride (60percent dispersion in mineral oil, 2.94 g, 73.5 mmol) and this was followed by <strong>[331-62-4]3-fluoro-4-methoxybenzonitrile</strong> (8.88 g, 58.8 mmol) and the resulting mixture was heated to 90° C. for 2 h under N2. After cooling, the mixture was partitioned between ether and H2 O, the organic layer washed sequentially with 0.5N HCl and saturated brine and then dried over MgSO4. Trituration with ether/pentane (1/, v/v) afforded the subtitle compound as an off-white solid (13.35 g, 71percent). Rf 0.27 (hexane/EtOAc 5/1, v/v). MS m/z 318, 320 (MH+). |
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