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CAS No. : | 1208434-90-5 | MDL No. : | MFCD22683867 |
Formula : | C9H10F2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KKWMGIQEJSZJLI-UHFFFAOYSA-N |
M.W : | 204.17 | Pubchem ID : | 18444706 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 45.47 |
TPSA : | 38.69 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.71 cm/s |
Log Po/w (iLOGP) : | 2.19 |
Log Po/w (XLOGP3) : | 1.18 |
Log Po/w (WLOGP) : | 2.16 |
Log Po/w (MLOGP) : | 1.76 |
Log Po/w (SILICOS-IT) : | 2.55 |
Consensus Log Po/w : | 1.97 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.97 |
Solubility : | 2.2 mg/ml ; 0.0108 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.59 |
Solubility : | 5.27 mg/ml ; 0.0258 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.05 |
Solubility : | 0.183 mg/ml ; 0.000897 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.77 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
71.4% | With lithium borohydride In tetrahydrofuran at 0 - 20℃; for 48 h; | To a solution of methyl 2,6-difluoro-3,5-dimethoxybenzoate (2.4g, 10.3mmol) in THF (20mL) at 0 °C, added 2M lithium borohydride in THF (15mL), stirred the reaction mass at room temperature for 2days and added another portion of lithium borohydride in THF (2.5mL). Stirring continued for further 2days at room temperature. Cooled the reaction mass to 0 °C and quenched with saturated NH4C1 solution. The aqueous solution extracted with ethyl acetate (3x20mL). The organic phase was washed with brine, dried over Na2S04, filtered and concentrated. The residue was purified by silica gel column chromatography to afford the title compound as a solid (1.5g, yield: 71.4percent). 1H-NMR (CDC13, 300MHz): δ 6.61 (t, 1H), 4.80 (d, 2H), 3.86 (s, 6H), 1.89 (brs, 1H). |
61% | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 4 h; | To a solution of LiA1H4 (727 mg, 19.l2mmol) in THF (30 mL) at 0°C was added a solution of methyl 2,6-difluoro-3,5-dimethoxybenzoate (2.96 g, 12.75 mmol) in THF (30 mL) dropwise. The resulting solution was stirred for 4 h at room temperature. The reaction was then quenched by the addition of water and aq. NaOH(15percent). The resulting solution was extracted withDCM and the organic layer was concentrated. The residue was purified by chromatography(hexane/ether (3:2)) to afford 1.58 g (61percent) of (2,6-difluoro-3,5-dimethoxyphenyl)methanol as acolorless semi-solid. |
43% | With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.5 h; | Step 2: Intermediate 2[00810j To an ice-cooled solution of Intermediate 1 (240 mg, 1.03 mmol) in THF was added LAH (60.0 mg, 1.58 mmol), and the mixture was stirred at 0 °C for 30 mi EtOAc and water were added and the resulting mixture was extracted with EtOAc, dried, and evaporated in vacuo. The resultant residue was purified through silica gel chromatography (eluted with 30percent EtOAc in Hexane) to afford the title compound (100 mg, 43percent). ‘H NMR (400 MHz, CDC13): ö 1.93 (t, 1H), 3.88 (s, 6H), 4.80 (d, 2H), 6.62 (t, 1H). |
8.67 g | With lithium borohydride In tetrahydrofuran at 20℃; for 87 h; Cooling with ice | Preparation Example 17 A mixture of methyl 2,6-difluoro-3,5-dimethoxybenzoate (10 g) and tetrahydrofuran (50 mL) was ice cooled, and lithium borohydride (3.0M tetrahydrofuran solution, 43 mL) was added thereto followed by stirring at room temperature for 65 hours. The reaction mixture was ice cooled again, and additional lithium borohydride (3.0M tetrahydrofuran solution, 14 mL) was added thereto followed by stirring at room temperature for 22 hours. The reaction mixture was ice cooled and slowly added into ice water (300 mL). Further, concentrated hydrochloric acid (25 mL) was slowly added thereto, and the resulting mixture was stirred at room temperature for 1 hour and extracted with toluene/ethyl acetate (1:1). An organic layer obtained was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and then filtered. The filtrate was concentrated under reduced pressure to give (2,6-difluoro-3,5-dimethoxyphenyl)methanol (8.67 g). |
8.67 g | With lithium borohydride In tetrahydrofuran at 20℃; for 87 h; Cooling with ice | (2) A mixture of methyl 2,6-difluoro-3,5-dimethoxybenzoate (10 g) and tetrahydrofuran (57 mL) was ice-cooled, and lithium borohydride (3.0 mol/L tetrahydrofuran solution, 43 mL) was added thereto, followed by stirring at room temperature for 65 hours. The reaction mixture was ice-cooled again, and additional lithium borohydride (3.0 mol/L tetrahydrofuran solution, 14.4 mL) was added thereto, followed by stirring at room temperature for 22 hours. The reaction mixture was ice-cooled and slowly added into ice water (300 mL) Further, concentrated hydrochloric acid (25 mL) was slowly added thereto, followed by stirring at room temperature for 1 hour and extracting with toluene/ethyl acetate (1:1). The organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure to obtain (2,6-difluoro-3,5-dimethoxyphenyl)methanol (8.67 g). MS (EI+): 204[(M)+]. |
8.67 g | With lithium borohydride In tetrahydrofuran at 20℃; for 65 h; Cooling with ice | (2) A mixture of methyl 2,6-difluoro-3,5-dimethoxybenzoate (10 g) and tetrahydrofuran (50 mL) was ice-cooled, and lithium borohydride (3.0 M tetrahydrofuran solution, 43 mL) was added thereto, followed by stirring at room temperature for 65 hours. The reaction mixture was ice-cooled again, and additional lithium borohydride (3.0 M tetrahydrofuran solution, 14 mL) was added thereto, followed by stirring at room temperature for 22 hours. The reaction mixture was ice-cooled and slowly added into ice water (300 mL). Further, concentrated hydrochloric acid (25 mL) was slowly added thereto, followed by stirring at room temperature for 1 hour and extracting with toluene/ethyl acetate (1:1). The organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and then filtered. The filtrate was concentrated under reduced pressure to obtain (2,6-difluoro-3,5-dimethoxyphenyl)methanol (8.67 g). |
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