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CAS No. : | 1221171-70-5 | MDL No. : | MFCD18909427 |
Formula : | C6H3ClF3NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GZFNUCAMADABAO-UHFFFAOYSA-N |
M.W : | 197.54 | Pubchem ID : | 49871750 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 35.93 |
TPSA : | 22.12 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) : | -5.1 cm/s |
Log Po/w (iLOGP) : | 1.94 |
Log Po/w (XLOGP3) : | 3.39 |
Log Po/w (WLOGP) : | 3.89 |
Log Po/w (MLOGP) : | 1.65 |
Log Po/w (SILICOS-IT) : | 2.58 |
Consensus Log Po/w : | 2.69 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.44 |
Solubility : | 0.072 mg/ml ; 0.000364 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.53 |
Solubility : | 0.0578 mg/ml ; 0.000293 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.27 |
Solubility : | 0.106 mg/ml ; 0.000535 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.92 |
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: |
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* 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 |
---|---|---|
62% | at 120℃; for 3.33333 h; Inert atmosphere | b) 2-chloro-6-(trifluoromethoxy)pyridine (1-5); To a mixture of SbF3 (29.87 g; 167.10 mmol; 2 eq) and SbCl5 (1.61 mL; 12.53 mmol; 0.15 eq) stirred under argon at 120°C, was added dropwise over 20 minutes 2-chloro-6- (trichloromethoxy)pyridine (20.63 g; 83.55 mmol; 1 eq). After 3 hours stirring at 120°C, the reaction mixture was cooled to room temperature and dichlorom ethane (350 mL) was added, followed by a saturated solution of sodium carbonate (350 mL) and an aqueous solution of 20percent KF (175 mL). The biphasic mixture was filtered on Celite.(R).. The 2 layers were separated and the aqueous layer was extracted with dichloromethane (5 x 100 mL). The combined organic layers were dried over sodium sulphate, filtered and concentrated to dryness. The crude obtained was purified under vacuum distillation (P = 35 mbars; T° = 81-83°C) to afford 2-chloro-6- (trifluoromethoxy)pyridine in 62 percent yield as a colorless oil.1H- MR (CDC13): δ (ppm) 6.96 (d, 1H); 7.27 (d, 1H); 7.75 (t, 1H). |
53% | at 120 - 150℃; | 2-Chloro-6-trifluoromethoxypyridine (2); 2-Chloro-6-trichloromethoxypyridine (1, 5.9 g, 23.8 mmol) was added dropwise to a molten mixture Of SbF3 (8.7 g, 47.7 mmol, 2.0 eq) and SbCl5 (1.0 g, 0.45 mL, 3.6 mmol, 0.15 eq) at 120 0C and stirred for 3 h at 150 0C. GC monitoring indicated 100percent conversion and disappearance of byproduct OCF2Cl. The mixture was then cooled to 0 0C and dissolved in dichloromethane (100 mL). The solution was quenched with saturated aqueous solution of sodium hydrogencarbonate (100 mL) and potassium fluoride (20percent, 50 mL), the aqueous layer was extracted with dichloromethane (2 x 50 mL). The combined organic layers were dried over sodium sulfate and the solvent was distilled. The crude product was distilled under vacuum to afford pure 2-chloro-6-trifiuoromethoxypyridine (2, 2.5 g, 10.1 mmol, 53percent) as a colorless oil; b.p. 42-44 0C / 20 mbar. - 1H NMR (CDCl3, 300 MHz): δ = 7.67 (t, J = 7.9 Hz, 1 H), 7.18 (d, J = 7.7 Hz, 1 H), 6.87 (d, J= 8.0 Hz, 1 H). - 13C NMR (CDCl3, 75 MHz): δ = 155.6, 149.3, 141.9, 122.2, 119.8 (q, J= 262 Hz), 111.8. - MS(EI): m/z = 197 [M+], 162 [M+-Cl]. |
53% | at 120 - 140℃; for 3 h; | 2-Chloro-6-trichloromethoxypyridine (1, 5.9 g, 24 mmol, 1 equiv.) was added dropwise at 120 °C to a mixture of SbF3 (8.7 g, 48 mmol, 2equiv.) and SbCl5 (0.60 mL, 4.8 mmol, 0.2 equiv.) and the mixture was stirred for 3 h at 140 °C. GC monitoring indicated 100percent conversion and disappearance of the−OCF2Cl byproduct. The mixture was then cooled to room temperature and dissolved in dichloromethane (100 mL). The solution was washed with 2 M HCl (150 mL) and the aqueous layer wa sextracted with dichloromethane (2 × 50 mL). The combined organic layers were dried over sodium sulphate and the solvent was evaporated at atmospheric pressure. The crude product was distilled under reduced pressure to afford pure 2-chloro-6-trifluoromethoxypyridine (2).Colourless oil (2.5 g, 53percent yield), b.p.= 42–44 °C (20 mbar); 1H NMR(CDCl3, 300 MHz, 25 °C): δ 7.67 (t, 1H, J =7.9 Hz, H-4), 7.18 (d, 1H,J = 7.9 Hz, H-5), 6.87 (d, 1H, J =7.9 Hz, H-3) ppm; 13C NMR (CDCl3,75 MHz, 25 °C): δ 155.6 (C), 149.3 (C), 142.0 (CHarom), 122.2(CHarom), 119.8 (q, JC-F= 262.1 Hz, OCF3), 111.1 (CH); 19F NMR(CDCl3, 282 MHz, 25 °C): δ −57.2 ppm. |
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