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CAS No. : | 260806-90-4 | MDL No. : | MFCD11042778 |
Formula : | C9H9BrO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YMRGVTKIFLNUFC-UHFFFAOYSA-N |
M.W : | 245.07 | Pubchem ID : | 46311082 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 51.91 |
TPSA : | 35.53 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) : | -5.86 cm/s |
Log Po/w (iLOGP) : | 2.41 |
Log Po/w (XLOGP3) : | 2.73 |
Log Po/w (WLOGP) : | 2.24 |
Log Po/w (MLOGP) : | 2.36 |
Log Po/w (SILICOS-IT) : | 2.39 |
Consensus Log Po/w : | 2.42 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.22 |
Solubility : | 0.147 mg/ml ; 0.000599 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.13 |
Solubility : | 0.182 mg/ml ; 0.000741 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.46 |
Solubility : | 0.085 mg/ml ; 0.000347 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.69 |
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 |
---|---|---|
99% | for 24 h; Reflux | General procedure: The benzoic acid (1-4 g)was dissolved in methanol (25-75 mL),before conc. H2SO4 (2-6 mL) was added dropwise while stirring.The reaction mixture was heated to reflux and stirred for 24 h. Thereaction mixture was quenched in a saturated aq NaHCO3 solution(100-200 mL) ensuring neutral to basic pH, and the aqueous phase was extracted with CH2Cl2 (4 x 50 mL). The combined organic phases were washed with saturated aq NaCl solution (25-50 mL),dried over anhydrous Na2SO4 and filtered. Concentration yielded the target compound in high yield and purity. ;Methyl 3-bromo-2-methoxybenzoate was prepared as described in Section 4.5 , starting with 3-bromo-2-methoxybenzoic acid (1.00 g, 4.33 mmol). The procedure yielded 1.07 g (4.33 mmol, 100percent) of methyl 3-bromo-2-methoxybenzoate as clear oil, HPLC-purity: 99percent, tR = 21.5 min; 1H NMR (600 MHz, DMSO-d6) δ: 7.88-7.84 (m, 1H), 7.73-7.70 (m, 1H), 7.18 (t, J = 7.8, 1H), 3.86 (s, 3H), 3.81 (s, 3H); 13C NMR (150 MHz, DMSO-d6) δ: 165.1, 155.7, 137.0, 130.3, 126.8, 125.6, 118.1, 61.8, 51.4; HRMS (APCI/ASAP, m/z): 244.9813 (calcd. C9H1079BrO3, 244.9813, [M+H]+). 1H NMR data are in accordance with that reported previously |
90% | With pyridine; oxalyl dichloride In dichloromethane at 20℃; | 3-Bromo-2-methoxybenzoic acid (2 g, 8.65 mmol, 1.0 eq) was dissolved in dry DCM and stirred for 10 minutes, cooled to 0 °C and slowly treated with oxalyl chloride (3.3 g, 25.9 mmol, 3 eq). Methanol in pyridine was added dropwise and the reaction mixture was stirred at ambient temperature. The solvents were evaporated under reduced pressure and the reaction mass was diluted with water. The aqueous mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous Na2SO4 and concentrated under vacuum to afford the desired product (1.9 g, 90percent). 1H NMR (400 MHz, CDCl3) δ 3.93 (s, 6H), 7.02-6.06 (t, 1H), 7.72-7.76 (m, 2H). MS (ESI): 247.0 (M + H)+. |
60% | Reflux | Concentrated sulphuric acid (2.0 ml) was slowly added to a solution of the commercially available 3-bromo-2-methoxybenzoic acid 23 (2.0 g, 8.66 mmol) in methanol (40.0 ml), and the mixture was refluxed overnight. Then the mixture was allowed to cool to room temperature and neutralized with saturated aqueous sodium bicarbonate solution. The aqueous layer was extracted several times with ethyl acetate, and the combined organic phases were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give pure 24 in 60percent yield. 1H NMR (200 MHz, CDCl3) δ (ppm): 3.92 (s, 6H), 7.03 (t, 1H, J = 7.9 Hz), 7.70 (dd, 1H, J = 6.4 Hz, J = 1.6 Hz), 7.74 (dd, 1H, J = 6.4 Hz, J = 1.6 Hz); MS: m/z 245 (M+, 100), 247 ([M + 2]+, 88), 214 ([M - OCH3]+, 72), 216 ([M + 2 - OCH3]+, 57). |
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