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CAS No. : | 1227509-94-5 | MDL No. : | MFCD16610401 |
Formula : | C6H5ClFNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LLSPCHCQVHEEMW-UHFFFAOYSA-N |
M.W : | 161.56 g/mol | Pubchem ID : | 51040787 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 35.33 |
TPSA : | 33.12 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) : | -6.32 cm/s |
Log Po/w (iLOGP) : | 1.61 |
Log Po/w (XLOGP3) : | 1.36 |
Log Po/w (WLOGP) : | 1.63 |
Log Po/w (MLOGP) : | 0.92 |
Log Po/w (SILICOS-IT) : | 2.27 |
Consensus Log Po/w : | 1.56 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.08 |
Solubility : | 1.35 mg/ml ; 0.00839 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.66 |
Solubility : | 3.55 mg/ml ; 0.022 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.74 |
Solubility : | 0.295 mg/ml ; 0.00182 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.82 |
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: |
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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 |
---|---|---|
91% | 6-Chloro-2-fluoro-3-pyridinemethanol (9b). A solution of 8b (2.00 g, 12.6 mmol) in MeOH (20 mL) was treated with NaBH4 (479 mg, 12.6 mmol) in portions over 5 min at - -10 C. The reaction was stirred at -10 C for 30 min. 10% aqueous hydrochloric acid was added dropwise to the reaction until pH 1 was reached and MeOH was removed under vacuum. The residue was extracted with CH2CI2 (50 mL x 3). The combined CH2CI2 layers were washed with H20 (50 mL) and brine (50 mL), dried (Na2S04), and concentrated to give 1.99 g of 9b as a white solid. Recrystallization from hexanes/EtOAc gave 1.84 g(91%) of pure 9b: Rf = 0.24 (3:1 hexanes/EtOAc); mp 60-61 C; 1H NMR 7.91 (dd, 1, J = 8.8, 8.0), 7.26 (d, 1, J = 8.0), 4.75 (d, 2, J = 4.8), 2.80 (t, 1, J = 4.8, OH); 13C NMR 159.1 (d, J = 244), 147.1 (d, J = 14), 141.6 (d, J = 6), 121.8 (d, J = 5.3), 121.4 (d, J = 27), 57.7; IR 3230; HRMS (EI) calcd for C6H5NC1F0 (M+) 161.0044, found 161.0052. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride;N,N-dimethyl-formamide; In dichloromethane; at 0 - 25℃; for 6.0h;Inert atmosphere; | 6-Chloro-2-fluoro-3-pyridineacetonitrile (lib). A solution of 9b (1.66 g, 10.3 mmol) in 10 mL of CH2C12 was treated with 10 mL of SOCl2 and 5 drops of DMF at 0 C. The resulting solution was stirred at 0 C for 1 h and then warmed to 25 C and stirred for another 5 h. The reaction was concentrated. The residue was dissolved in 50 mL of CH2CI2 and the solution was washed with saturated NaHC03 and brine, dried (Na2S04), and concentrated to give 1.93 g of crude 6-chloro-3-(chloromethyl)-2-fluoropyridine (10b), which was used without further purification. A small portion of crude 10b was recrystallized to give an analytical sample: 1H NMR 7.85 (dd, 1, J = 9.2, 8.0), 7.28 (d, 1, J = 8.0), 4.59 (s, 2); 13C NMR 159.4 (d, J = 246), 148.7 (d, J = 14), 143.2 (d, J = 4.5), 122.2 (d, J = 5.1), 118.2 (d, J = 28), 37.9; IR 1603, 1573, 1437, 1398; HRMS (EI) calcd for C6H4NC12F (M+) 178.9705, found 178.9710. Powdered NaCN (1.10 g, 22.4 mmol) was added to 20 mL of DMSO. The mixture was stirred at 25 C for 20 min. A solution of crude 10b in 5 mL of DMSO was added to the NaCN suspension dropwise over 10 min. The NaCN fully dissolved after addition. The resulting solution was stirred for 1 h at 25 C and cooled to 0 C. Water (100 mL) was added slowly to the reaction and the mixture was extracted with CH2CI2 (50 mL x 3). The combined organic layers were washed with H20 and brine, dried (Na2S04), and concentrated to give 1.50 g of crude lib. Flash chromatography (6: 1 hexanes/EtOAc to 3: 1 hexanes/EtOAc) gave 1.23 g of pure lib. Recrystallization gave 1.10 g (63%) of analytically pure lib: Rf = 0.37 (3: 1 hexanes/EtOAc); mp 47-48 C; 1H NMR 7.89 (dd, 1, J = 9.2, 8.0), 7.33 (d, 1, J = 8.0), 3.78 (s, 2); 13C NMR 159.2 (d, J = 246), 148.9 (d, J = 14), 142.3 (d, J = 4.1), 122.4 (d, J = 5.3), 115.4, 111.2 (d, J = 29), 17.2; IR 2261; HRMS (EI) calcd for C7H4N2C1F (M+) 170.0047, found 170.0055. |
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