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CAS No. : | 369-26-6 | MDL No. : | MFCD08689743 |
Formula : | C8H8FNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ABELEDYNIKPYTP-UHFFFAOYSA-N |
M.W : | 169.15 | Pubchem ID : | 12541234 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 42.08 |
TPSA : | 52.32 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) : | -6.1 cm/s |
Log Po/w (iLOGP) : | 1.7 |
Log Po/w (XLOGP3) : | 1.74 |
Log Po/w (WLOGP) : | 1.62 |
Log Po/w (MLOGP) : | 1.75 |
Log Po/w (SILICOS-IT) : | 1.4 |
Consensus Log Po/w : | 1.64 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.22 |
Solubility : | 1.01 mg/ml ; 0.00598 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.46 |
Solubility : | 0.593 mg/ml ; 0.0035 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.39 |
Solubility : | 0.692 mg/ml ; 0.00409 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.38 |
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 |
---|---|---|
100% | With hydrogen In ethyl acetate at 20℃; | Step B: Methyl 3-amino-4-fluorobenzoate; To a solution of methyl 4-fluoro-3-nitrobenzoate (6.57 g, 33 mmol) in EtOAc (75 mL) was added 10percent palladium on carbon (0.66 g). The suspension was transferred to a Fisher-Porter flask and installed in a hydrogenation apparatus. The flask was charged with H2 (25 psi) and stirred overnight at rt. The palladium was removed by filtration through a Celite plug, and the product was concentrated to generate a yellow oil, which darkened upon standing, in quantitative yield (5.51 g, 33 mmol). MS (ESI) m/z = 170 [M+H]+. |
68% | With hydrogenchloride; iron In methanol; water for 48 h; Reflux; Inert atmosphere | To a stirring solution of 4-fluoro-3-nitrobenzoic acid (25 g, 126 mmol) in MeOH (20 mL) was added Fe (28 g, 502 mmol), followed by addition of con. HCl (5 mL). The mixture was heated to reflux for two days, cooled to room temperature, and then filtered. The filtrate was concentrated in vacuo to give the desired product as a solid (15 g, 68percent). LC-MS (ES) m/z = 170.1 (M+H)+ 1H NMR (400 MHz, MeOD) δ ppm 7.39 (m, 2 H), 6.94 (m, 1 H), 3.91 (br, 5 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | at 0℃; for 12 h; Reflux | To a stirred solution of 3-amino-4-fluoro-benzoic acid (25 g, 161 mmol) in methanol (300 mL) was added thionyl chloride (30 mL, 403 mmol) dropewise at 0° C. Then the mixture solution was refluxed for 12 hours before cooling to room temperature. Then the reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (500 mL), washed with saturated aqueous sodium bicarbonate solution (3.x.100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3-amino-4-fluoro-benzoic acid methyl ester (27.5 g, quant.) as a pale-white solid: LC/MS m/e calcd for C8H8FNO2 (M+H)+: 170.16, observed: 169.9 |
89% | for 20 h; Reflux | Step 1: Preparation of methyl 3-amino-4-fluorobenzoate (54) To a mixture of 3-amino-4-fluorobenzoic acid (1 g, 6.45 mmol) in MeOH (20 ml), conc. H2SO4 (0.687 ml, 12.89 mmol) was added drop wise, and the reaction was refluxed for 20 hours. After cooling to room temperature the solvent was evaporated and the residue was partitioned between aq. NaHCO3 sat. sol. and ethyl acetate; the organic phase was washed with brine, dried over Na2SO4 and evaporated to dryness affording methyl 3-amino-4-fluorobenzoate as a brown solid (0.970 g, 5.73 mmol, 89percent yield, MS/ESI+170.0 [MH]+) (43) |
290 mg | Reflux | 3-amino-4-fluorobenzoic acid (0.5g) was dissolved in methanol (lOml), then concentrated sulfuric acid (lml) was added. The reaction solution was heated to reflux until the reaction is complete. Then the reaction mixture was cooled down and poured into water, the pH of the resultant solution was adjusted to 8 by 2N NaOH solution. The product was extracted to EtOAc layer and the solvent was stripped off. 290mg of methyl 3-amino-4- fluorobenzoate was obtained. |
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