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CAS No. : | 1000574-79-7 | MDL No. : | MFCD09878206 |
Formula : | C7H6BrF2NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QAIJRQYZGRRNFA-UHFFFAOYSA-N |
M.W : | 238.03 | Pubchem ID : | 26599226 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 45.14 |
TPSA : | 35.25 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) : | -5.73 cm/s |
Log Po/w (iLOGP) : | 1.86 |
Log Po/w (XLOGP3) : | 2.85 |
Log Po/w (WLOGP) : | 3.48 |
Log Po/w (MLOGP) : | 2.22 |
Log Po/w (SILICOS-IT) : | 2.21 |
Consensus Log Po/w : | 2.52 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.35 |
Solubility : | 0.106 mg/ml ; 0.000447 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.25 |
Solubility : | 0.134 mg/ml ; 0.000564 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.25 |
Solubility : | 0.135 mg/ml ; 0.000569 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.62 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-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 |
---|---|---|
83% | With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In acetonitrile; at 20.0℃; for 6.0h; | (25a) N-[2-Bromo-4-(difluoromethoxy)phenyl]formamide Into acetonitrile (80 mL), <strong>[1000574-79-7]2-bromo-4-(difluoromethoxy)aniline</strong> (4.40 g, 18.5 mmol) and formic acid (1.1 mL, 27.5 mmol) were dissolved, to which 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (7.7 g, 28 mmol) and 4-methylmorpholine (3 mL, 27 mmol) were added, followed by stirring at room temperature for six hours. Ethyl acetate and water were added for extraction, and the resulting organic layer was sequentially washed with water and saturated brine and then dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue thus obtained was purified by silica gel column chromatography (hexane : ethyl acetate, 100 : 0 - 60 : 40, V/V) to give the desired title compound (4.1 g, yield 83%). 1H-NMR (CDCl3) 5: 6.47 (1H, t, J = 73.0 Hz), 7.13 (1H, dd, J = 9.1, 2.6 Hz), 7.39 (1H, d, J = 2.6 Hz), 7.58 (1H, br s), 8.41 (1H, d, J = 9.1 Hz), 8.49 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 90.0℃;Inert atmosphere; | Into a 250-mL round-bottom flask purged with and maintained under nitrogen was placed 2- bromo-4-(difluoromethoxy)benzenamine (7.9 g, 33.2 mmol), dioxane (100 mL), water (10 mL), CS2CO3 (32.46 g, 99.63 mmol), 4,4,5,5-tetramethyl-2-(prop-l-en-2-yl)-l,3,2-dioxaborolane (8.36 g, 49.8 mmol), and Pd(dppf)Cl2 (1.21 g, 1.65 mmol). The resulting solution was stirred overnight at 90C. The solids were filtered out. The filtrate was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with a gradient of ethyl acetate/petroleum ether (1 :30 to 1 :20). This resulted in 5.3 g (80%) of the title compound as a yellow solid. MS-ESI: 200.1 (M+l). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With N-Bromosuccinimide; In dichloromethane; for 3h;Reflux; | In a 250-mI four-necked flask equipped with a mechanical stirrer, a constant-pressure dropping funnel, a reflux condenser, and a thermometer, add 16 g of <strong>[22236-10-8]4-difluoromethoxyaniline</strong> and 100 mL of dichloromethane.18 g of N-bromosuccinimide (NBS) was dissolved in 100 mL of dichloromethane, and the N-bromosuccinimide (NBS) solution was dropped into the <strong>[22236-10-8]4-difluoromethoxyaniline</strong> solution while stirring at room temperature.Stir at reflux for 3 h. Thin-layer chromatography (TLC, dichloromethane: methanol volume ratio 3: 1) is followed to the end of the reaction. The reaction solution is concentrated to remove the organic solvent.That is, 4-difluoromethoxy-2-bromoaniline was obtained as a light-colored powdery solid product with a yield of 93% and a purity of 95%. |
53% | With N-Bromosuccinimide; In acetonitrile; at 20℃; for 1h;Inert atmosphere; | Into a 250-mL round-bottom flask purged with and maintained under nitrogen was placed 4- (difluoromethoxy)benzenamine (10 g, 62.8 mmol), ACN (100 mL), and BS (5.59 g, 31.4 mmol). The resulting solution was stirred for 1 h RT and then was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with a gradient of ethyl acetate/petroleum ether (1 :20 to 1 : 10). This resulted in 7.9 g (53%) of the title compound as red oil. MS-ESI: 238.0/240.0 (M+l). |
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