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CAS No. : | 375368-83-5 | MDL No. : | MFCD03095092 |
Formula : | C6H5BrFN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GUYGQQWIKZLHTP-UHFFFAOYSA-N |
M.W : | 190.01 | Pubchem ID : | 17750149 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 36.86 |
TPSA : | 12.89 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) : | -5.77 cm/s |
Log Po/w (iLOGP) : | 2.08 |
Log Po/w (XLOGP3) : | 2.38 |
Log Po/w (WLOGP) : | 2.71 |
Log Po/w (MLOGP) : | 2.01 |
Log Po/w (SILICOS-IT) : | 2.92 |
Consensus Log Po/w : | 2.42 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.01 |
Solubility : | 0.185 mg/ml ; 0.000975 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.29 |
Solubility : | 0.971 mg/ml ; 0.00511 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.55 |
Solubility : | 0.054 mg/ml ; 0.000284 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.68 |
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 |
---|---|---|
78% | at -20 - 20℃; for 4 h; | 5-Bromo-2-amino-6-methylpyridine (5g) was added to pyridine hydrogen fluoride (35 mL).The reaction was cooled to -20 ° C and then KNO 2 (2.7 g) was added.The reaction was continued for 4 hours after rising to room temperature.The reaction mixture was poured into 200 mL of ice water and extracted with dichloromethane (50 mL EtOAc).The extracts were combined, washed with 1N hydrochloric acid, and concentrated to give 5-bromo-2-fluoro-6-methylpyridine (4 g, yield 78percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | at 100℃; for 2 h; | NaCN (4 g, 82 mmol) was added to a solution of 3-bromo-6-fluoro-2-methyl-pyridine (4 g, 21 mmol) in DMSO (100 mL) The mixture was stirred for 2 h at 100° C., poured into H2O (100 mL) and extracted with ethyl acetate (2.x.100 mL). The organic layers were dried over Na2SO4, concentrated and purified by flash column chromatography (silica gel, 10 g, eluting with 10percent ethyl acetate in petroleum ether) to give the title compound (0.6 g, 15percent) as white solid; MS (D): m/e=197.0 [M+H]+. |
15% | at 100℃; for 2 h; | NaCN (4 g, 82 mmol) was added to a solution of 3-bromo-6-fluoro-2-methyl-pyridine (4 g, 21 mmol) in DMSO (100 mL) The mixture was stirred for 2 h at 100°C, poured into H20 (100 mL) and extracted with ethyl acetate (2 x lOOmL). The organic layers were dried over Na2S04, concentrated and purified by flash column chromatography (silica gel, 10 g, eluting with 10percent ethyl acetate in petroleum ether) to give the title compound (0.6 g, 15percent) as white solid; MS (EI): m/e = 197.0 [M+H]+. |
15% | at 100℃; for 2 h; | a) 5-Bromo-6-methyl-pyridine-2-carbonitrile NaCN (4 g, 82 mmol) was added to a solution of 3-bromo-6-fluoro-2-methyl-pyridine (4 g, 21 mmol) in DMSO (100 mL) The mixture was stirred for 2 h at 100 °C, poured into H20 (100 mL) and extracted with ethyl acetate (2 x lOOmL). The organic layers were dried over Na2S04, concentrated and purified by flash column chromatography (silica gel, 10 g, eluting with 10percent ethyl acetate in petroleum ether) to give the title compound (0.6 g, 15percent) as white solid; MS (EI): m/e = 197.0 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | at 60℃; for 18 h; Large scale | 5-bromo-2-fluoro-6-methylpyridine (5kg) was dissolved in concentrated sulfuric acid (50kg).After the reaction was warmed to 60 ° C, CrO3 (16 kg) was added in portions. After the addition was completed, the reaction was continued for 18 hours. TLC monitors the reaction. After the reaction was completed, the reaction was neutralized by adding NaOH (20percent) to neutrality. Further ethyl acetate extraction (50 L X 3) was added.After combining the extracts, they were dried and concentrated. The crude product obtained was beaten with n-hexane. Filter and dry to obtain pure 3-bromo-6-fluoropicolinic acid (3.8 kg, yield 58percent). |
45% | With potassium permanganate In water for 5 h; Reflux | Water (1600 mL) was added to 3-bromo-6-fluoro-2-methylpyridine (60 g, 0.32 mol), mechanically stirred and heated to reflux , potassium permanganate (220 g, 1.4 mol) was added to the flask in 11 portions at intervals of 15 min, after the addition, the reflux was continued for 5 h. The reaction solution was cooled to room temperature, suction filtered, and the filtrate was adjusted to pH 5 with dilute hydrochloric acid, then, the filtrate was spun dry, and then anhydrous ethanol (500 ml) was added thereto, and the mixture was stirred under reflux for 30 min, filtered while hot, and the filtrate was dried to give 3-bromo-6-fluoro-2-picolinic acid (31 g, 45percent). |
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