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CAS No. : | 321-21-1 | MDL No. : | MFCD04115880 |
Formula : | C8H7FO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KDXOONIQRUZGSY-UHFFFAOYSA-N |
M.W : | 154.14 | Pubchem ID : | 3860639 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 38.33 |
TPSA : | 37.3 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) : | -5.88 cm/s |
Log Po/w (iLOGP) : | 1.45 |
Log Po/w (XLOGP3) : | 1.92 |
Log Po/w (WLOGP) : | 2.25 |
Log Po/w (MLOGP) : | 2.36 |
Log Po/w (SILICOS-IT) : | 2.09 |
Consensus Log Po/w : | 2.02 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.34 |
Solubility : | 0.7 mg/ml ; 0.00454 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.33 |
Solubility : | 0.726 mg/ml ; 0.00471 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.42 |
Solubility : | 0.583 mg/ml ; 0.00378 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.18 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
95% | at 80℃; for 3 h; | Step 1. Methyl 4-fluoro-2-methylbenzoate A solution of 4-fluoro-2-methylbenzoic acid (50 g, 324.38 mmol) and SOCl2 (77 g, 648.76 mmol) in methanol (200 mL) was heated to reflux for 3 hours at 80° C. Then, the mixture was concentrated in vacuo to afford methyl 4-fluoro-2-methylbenzoate as brown oil (52 g, 95percent). 1H-NMR (300 MHz, CDCl3): δ 7.92-7.98 (m, 1H), 6.88-6.95 (m, 2H), 3.90 (s, 3H), 2.61 (s, 3H) |
78% | at 130℃; for 1 h; Microwave irradiation | Preparation 7; Preparation of methyl 4-fluoro-2-methylbenzoate; In a cylindrical quartz tube was placed 4-fluoro-2-methyl-benzoic acid (1.5 g, 9.7 mmol) in MeOH (15 ml) and 2 drops of H2SO4 cone, were added. The tube was introduced into a Smith Creator.(R). Personal chemistry microwave reactor.Microwave irradiation was carried out at 1300C for 1h until HPLC revealed the disappearance of the starting-material.The mixture was allowed to cool down and the solvent was removed under reduced pressure. The crude was diluted with DCM and washed with NaHCOssat. The organic phase was dried over anhydrous Na2SU4 and concentration of the solution gave the final compound (1.3g, 78percent) as colourless oil. 1 H-NMR (400 MHz), δ (ppm, DMSO-de): 7.91 (dd, J = 6.2, 8.7 Hz, 1H), 7.22 (dd, J = 2.6, 10.2 Hz, 1H), 7.15 (td, J =2.4, 8.4 Hz, 1H), 3.83 (s, 3H), 2.54 (s, 3H) |
52% | for 40 h; Heating / reflux | A solution of the compound of Example 144 (8.93 g, 57.9 mmol) and sulfuric acid (0.75 ML) in methanol (150 ML) was refluxed 40 h.. The reaction mixture was cooled in an ice bath, and the acid was neutralized to PH 7 with sodium bicarbonate.. The solution was concentrated under reduced pressure.. Diethyl ether and brine were added to the crude residue.. The organic layer was dried over magnesium sulfate, and the solvent was removed in vacuo to yield 5.1 g of the title compound (52percent). Rf=0.72 (silica gel, 5percent isopropanol/dichloromethane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With sulfuric acid In methanol; diethyl ether | Example 145 Preparation of methyl 2-methyl-4-fluorobenzoate STR221 A solution of the compound of Example 144 (8.93 g, 57.9 mmol) and sulfuric acid (0.75 mL) in methanol (150 mL) was refluxed 40 h. The reaction mixture was cooled in an ice bath, and the acid was neutralized to pH 7 with sodium bicarbonate. The solution was concentrated under reduced pressure. Diethyl ether and brine were added to the crude residue. The organic layer was dried over magnesium sulfate, and the solvent was removed in vacuo to yield 5.1 g of the title compound (52percent). Rf=0.72 (silica gel, 5percent isopropanol/dichloromethane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | at 0 - 20℃; for 6 h; Inert atmosphere | [000146] To a stirred solution of 4-fluoro-2-methylbenzoic acid 83 (500 mg, 3.24 mmol) in concentrated sulfuric acid (2.5 mL) under inert atmosphere was added potassium nitrate (655 mg, 6.49 mmol) at 0 °C; warmed to RT and stirred for 6 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was quenched with ice water (20 mL), filtered the precipitated solid and dried in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 5percent MeOH/ CH2C12 to afford compound 84 (300 mg, 60percent) as brown syrup. TLC: 10percent MeOH/ CH2C12 (R 0.3); 1H-NMR (DMSO-d6, 500 MHz): ö 13.56 (br s, 1H), 8.52 (d, J= 8.0 Hz, 1H), 7.61 (d, J 12.5 Hz, 1H), 2.63 (s, 3H). |
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