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CAS No. : | 19346-44-2 | MDL No. : | MFCD09475421 |
Formula : | C6H5FN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MASVTBZQAKGYJA-UHFFFAOYSA-N |
M.W : | 156.12 | Pubchem ID : | 12408183 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 37.98 |
TPSA : | 58.71 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) : | -6.2 cm/s |
Log Po/w (iLOGP) : | 1.06 |
Log Po/w (XLOGP3) : | 1.48 |
Log Po/w (WLOGP) : | 1.86 |
Log Po/w (MLOGP) : | 0.04 |
Log Po/w (SILICOS-IT) : | 0.09 |
Consensus Log Po/w : | 0.91 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.08 |
Solubility : | 1.3 mg/ml ; 0.00836 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.32 |
Solubility : | 0.747 mg/ml ; 0.00479 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.06 |
Solubility : | 1.37 mg/ml ; 0.00875 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.01 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P280-P305+P351+P338-P233 | UN#: | |
Hazard Statements: | H302-H315-H317-H319-H319-H332-H335 | Packing Group: | |
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 |
---|---|---|
89% | 3-Amino-2-fluoro-5-methylpyridine was prepared analogously from <strong>[19346-44-2]2-fluoro-5-methyl-3-nitropyridine</strong>. This compound was obtained in 89 percent yield as white solid melting at 27-28.5 C. Elemental Analysis C6 H7 FN2 Calc.: %C, 57.1; %H, 5.59; %N, 22.2 Found: %C, 56.9, %H, 5.65; %N, 22.6 1 H NMR CDCl3: 7.2 (d, 1H); 6.8 (d, 1H); 3.7 (br, 2H); 2.1 (s, 3H); 13 C NMR CDCl3: 151.8 (d, J=229); 134.5 (d, J=12.6); 132.2 (d, J=3.9); 129.9 (d, J=28.7); 125.8 (d, J=5.3), 17.8. | |
89% | 3-Amino-2-fluoro-5-methylpyridine was prepared analogously from <strong>[19346-44-2]2-fluoro-5-methyl-3-nitropyridine</strong>. This compound was obtained in 89 percent yield as white solid melting at 27-28.5 C. Elemental Analysis C6 H7 FN2 Calc.: %C, 57.1; %H, 5.59; %N, 22.2 Found: %C, 56.9; %H, 5.65; %N, 22.6 1 H NMR CDCl3: 7.2 (d, 1H); 6.8 (d, 1H); 3.7 (br, 2H); 2.1 (s, 3H); 13 C NMR CDCl3: 151.8 (d, J=229); 134.5 d, J=12.6); 132.2 (d, J=3.9); 129.9 (d, J=28.7); 125.8 (d, J=5.3), 17.8. | |
89% | 3-Amino-2-fluoro-5-methylpyridine was prepared analogously from <strong>[19346-44-2]2-fluoro-5-methyl-3-nitropyridine</strong>. This compound was obtained in 89 percent yield as white solid melting at 27-28.5 C. Elemental Analysis C6 H7 FN2 Calc.: %C, 57.1; %H, 5.59; %N, 22.2 Found: %C, 56.9, %H, 5.65; %N, 22.6 1 H NMR CDCl3: 7.2 (d, 1H); 6.8 (d, 1H); 3.7 (br, 2H); 2.1 (s, 3H); 13 C NMR CDCl3: 151.8 (d, J=229); 134.5 (d, J=12.6); 132.2 (d, J=3.9); 129.9 (d, J=28.7); 125.8 (d, J=5.3), 17.8. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | In propan-1-ol; for 0.5h;Heating; | General procedure: The dimethyl derivatives (4,4?, 5,5? or 6,6?) of 3,3?-dinitro-2,2?-azobipyridine were synthesized from the respective hydrazo-derivatives obtained previously from 3-nitro-4(or 5 or 6)-methyl-2-hydrazine-pyridine, respectively. Syntheses of these hydrazo derivatives were very similar to the synthesis of 3,3?-dinitro-2,2?-hydrazobipyridine. Instead of ethanol n-propanol was used and its mixtures were heated at boiling temperature for 30 min in the water bath. 2.52 g (0.015 mol) of 3-nitro-4(or 5 or 6)-methyl-2-hydrazine-pyridine were used to synthesis. The synthesized red-brown needle-like crystals of 4,4?-dimethyl-3,3?-dinitro-2,2?-hydrazobipyridine melt with decomposition at 255C. The yield was 53.1%. The synthesized brown needle-like crystals of 5,5?-dimethyl-3,3?-dinitro-2,2?-hydrazobipyridine melt with decomposition at 285C. The yield was 54.0%. The synthesized dark-brown needle-like crystals of 6,6?-dimethyl-3,3?-dinitro-2,2?-hydrazobipyridine melt with decomposition at 275C. The yield was 51.0%. 1 g of the obtained in this way 4,4?(or 5,5? or 6,6?)-3,3?-dinitro-2,2?-hydrazobipyridine was used to obtain respective azo derivatives in the same way as 3NAP. The synthesized orange needle-like crystals of 4,4?-dimethyl-3,3?-dinitro-2,2?-azobipyridine (4M3NAP) melt with decomposition at 260C. The yield was 74.2%. The synthesized orange needle-like crystals of 5,5?-dimethyl-3,3?-dinitro-2,2?-azobipyridine (5M3NAP) melt with decomposition at 256C. The yield was 77.1%. The synthesized orange powder of 6,6?-dimethyl-3,3?-dinitro-2,2?-azobipyridine (6M3NAP) melt with decomposition at 206C. The yield was 80.3% [51,52,54]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35.5% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 48.0h;Inert atmosphere; Reflux; | To a stirred solution of <strong>[19346-44-2]2-fluoro-5-methyl-3-nitropyridine</strong> 4a (3.0 g, 19.22 mmol) in carbon tetrachloride (80 mL) were added azodiisobutyronitrile (316 mg, 1.90 mmol) and N-bromosuccinimide (3.76 g, 21.14 mmol). The reaction mixture was heated at reflux for 48 h under an argon atmosphere and then the contents were cooled to room temperature. The insoluble solid was removed by filtration, the filtrate was diluted with dichloromethane (50 mL) and washed with saturated aqueous sodium bicarbonate (30 mL×4) and brine (20 mL×2), dried over anhydrous magnesiumsulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/dichloromethane/ ethyl acetate = 15:1:1) to give the title compound 5a (1.8 g, 35.5%). White solid; mp 73-75 C; 1H NMR (400 MHz, CDCl3) delta (ppm): 8.56 (d, J = 8.4 Hz, 1H), 8.50 (s, 1H), 4.52 (s, 2H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | LiHMDS l.5M in THF (2.6 mL; 3.84 mmol) was added dropwise at 5C to a solutionof 4-methyl-3-(hydroxymethyl)morpholine (420 mg; 3.20 mmol) in Me-THF (12 mL).After 30 mi <strong>[19346-44-2]2-fluoro-5-methyl-3-nitropyridine</strong> (500 mg; 3.20 mmol) was quickly added and the reaction mixture was allowed to warm to room temperature and stirredrt overnight. LiHMDS 1 .5M in THF (854 p1; 1.28 mmol) was added at 0C and the mixture was stirred at rt for 5h. The reaction mixture was poured onto iced water, a10% aqueous solution of K2C03 and extracted with EtOAc. The organic layer was decanted, washed with water, dried over MgSO4, filtered and evaporated to give 733 mg of crude. The crude was purified by chromatography over silica gel (SiOH, GraceResolv, 12 g, Mobile phase DCM/MeOH/NH4OH, Gradient from: 99% DCM, 1% MeOH, 0.1% NH4OH to 97% DCM, 3% MeOH, 0.3% NH4OH). The pure fractionswere collected and the solvent was evaporated to give 544 mg of intermediate 445 (64% yield, yellow solid). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With potassium carbonate; In acetonitrile; at 80℃; for 5.0h; | [0205] A solution of <strong>[19346-44-2]2-fluoro-5-methyl-3-nitropyridine</strong> (1 g, 6.41 mmol), 4~(2,4~ difluorophenoxy)piperidine hydrochloride (1.919 g, 7.69 mmol) and K2CO3 (2.66 g, 19.22 mmol) in ACN (16.01 mL) was stirred at 80C for 5 hours. The reaction mixture was poured into water and extracted with EtOAc (3 x 50 mL). The organic layers were combined, dried over Na,2S(>4, and filtered. The filtrate was concentrated in vacuo and purified by flash chromatography (I SCO column) eluiing with a gradient of 0-100% EtOAc in heptane to give the title compound as a yellow solid (2.21 g, 99%). NMR (500 MHz, DMSQ-<:) delta ppm 1.66 - 1.73 (m, 2 H), 2.00 (d, J=12.20 Hz, 2 H), 2.25 (s, 3 H), 3.19 - 3.25 (m, 2 H), 3.52 - 3.57 (m, 2 H), 4.58 (dt, J=7,69, 3.72 Hz, 1H), 6,98 - 7.04 (m, 1H), 7.26 - 7.34 (m, 2 H), 8.1 1 (s, 1H), 8.28 -MS m/z [M+H 350.2, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In acetonitrile; at 20℃; | [0261] A solution of ferf-butyl piperazine-l -carboxylate (7.75 g, 41.6 mmol), 2-fluoro-5- methyl-3-nitropyridine (5 g, 32.0 rnmol) and K2CO.3 (13.28 g, 96 mmol) in ACN (80 mL) was stirred at RT overnight. The reaction mixture was filtered with suction and the solvent removed under reduced pressure to give the title product which was used without further purification. -MS m/z [M+Hf 323.2. |
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