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CAS No. : | 133059-43-5 | MDL No. : | MFCD03095000 |
Formula : | C7H4BrFO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SWHUROFMIMHWKS-UHFFFAOYSA-N |
M.W : | 203.01 | Pubchem ID : | 2783411 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 39.49 |
TPSA : | 17.07 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) : | -5.99 cm/s |
Log Po/w (iLOGP) : | 1.69 |
Log Po/w (XLOGP3) : | 2.18 |
Log Po/w (WLOGP) : | 2.82 |
Log Po/w (MLOGP) : | 2.63 |
Log Po/w (SILICOS-IT) : | 3.08 |
Consensus Log Po/w : | 2.48 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.85 |
Solubility : | 0.287 mg/ml ; 0.00141 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.17 |
Solubility : | 1.37 mg/ml ; 0.00673 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.48 |
Solubility : | 0.0668 mg/ml ; 0.000329 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.19 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H319 | 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 |
---|---|---|
97% | Stage #1: With sodium tetrahydroborate In methanol at 0 - 20℃; for 2 h; Stage #2: With hydrogenchloride In methanol; water |
Step i :Solid NaBH4 (603 mg, 15.9 mmol) is added to a solution of ketone 50a (4.11 g, 19.92 mmol) dissolved in MeOH (62 mL) at O0C. The reaction is warmed to RT and is allowed to stir for 2 h. The reaction is quenched with aqueous HCI (1 N, 20 mL), the MeOH is removed by concentration and the product extracted with EtOAc (2 x 50 <n="111"/>mL). The organic layer is washed with brine (50 ml_), dried over MgSO4, filtered and concentrated to afford alcohol 50b (4.1 g, 97percent yield). This material is used as is in the next step. |
97% | With sodium tetrahydroborate In methanol at 0 - 25℃; for 2 h; | Solid NaBH4 (603 mg, 15.9 mmol) is added to a solution of aldehyde 48a (4.1 1 g,19.92 mmol) dissolved in MeOH (62 mL) at O0C. The reaction is warmed to RT and is allowed to stir for 2 h. The reaction is quenched with aqueous HCI (1 N, 20 mL), the MeOH is removed by concentration and the product extracted with EtOAc (2 x 50 mL). The organic layer is washed with brine (50 mL), dried over MgSO4, filtered and concentrated to afford alcohol 48b (4 1 g, 97percent yield). This material is used as is in the next step. |
97% | With methanol; sodium tetrahydroborate In tetrahydrofuran | To a solution of 4-bromo-3-fluorobenzaldehyde (10 g, 49.3 mmol) and NaBH4 (3.73 g, 99 mmol) in THF (100 mL) was added MeOH (100 mL) dropwise at 20° C. After LCMS analysis showed the starting material had disappeared, the solvent was removed in vacuo. The residue was dissolved in DCM (200 mL) and washed with H2O (60 mL) and brine (60 mL). The organic layer was dried over Na2SO4, filtered and concentrated to yield a white solid of (4-bromo-3-fluorophenyl)methanol (9.8 g, 47.7 mmol, 97.0percent yield): 1H NMR (400 MHz, CD3OD) δ 7.54 (t, J=7.8 Hz, 1H), 7.18 (d, J=9.6 Hz, 1H), 7.06 (d, J=7.2 Hz, 1H), 4.56 (s, 2H); ES-LCMS m/z 188.9 (M-17). |
97% | With sodium tetrahydroborate In tetrahydrofuran; methanol at 20℃; | To a solution of 4-bromo-3-fluorobenzaldehyde (10 g, 49.3 mmol) and NaBH4 (3.73 g, 99 mmol) in THF (100 mL) was added MeOH (100 inL) dropwise at 20 °C. After LCMS analysis showed the starting material had disappeared, the solvent was removed in vacuo. The residue was dissolved in DCM (200 mL) and washed with H20 (60 mL) and brine (60 mL). The organic layer was dried over Na2S04, filtered and concentrated to yield a white solid of (4-bromo-3- fluorophenyl)methanol (9.8 g, 47.7 mmol, 97.0percent yield): lH NMR (400 MHz, CD3OD) δ 7.54 (t, J = 7.8 Hz, 1H), 7.18 (d, J = 9.6 Hz, 1H), 7.06 (d, J = 7.2 Hz, 1H), 4.56 (s, 2H); ES-LCMS m/z 188.9 (M-17). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With manganese(IV) oxide In chloroform at 20℃; | To a solution of (4-bromo-3-fluoro-phenyl)-methanol (4.3 g, 21 mmol) in CHCl3 (50 mL) was added manganese dioxide (18.7 g, 210 mmol), and the resulting mixture was stirred overnight at room temperature until the starting material had been consumed. After filtration, the filtrate was concentrated in vacuo to give product (2.3 g, 55percent). |
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