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CAS No. : | 275383-87-4 | MDL No. : | MFCD08448149 |
Formula : | C6H5Cl2NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UJLNNNMWIMJFIW-UHFFFAOYSA-N |
M.W : | 178.02 | Pubchem ID : | 17750383 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 40.38 |
TPSA : | 33.12 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) : | -6.49 cm/s |
Log Po/w (iLOGP) : | 1.93 |
Log Po/w (XLOGP3) : | 1.26 |
Log Po/w (WLOGP) : | 1.73 |
Log Po/w (MLOGP) : | 1.09 |
Log Po/w (SILICOS-IT) : | 2.48 |
Consensus Log Po/w : | 1.7 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.12 |
Solubility : | 1.36 mg/ml ; 0.00766 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.55 |
Solubility : | 4.97 mg/ml ; 0.0279 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.08 |
Solubility : | 0.146 mg/ml ; 0.000822 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.66 |
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 |
---|---|---|
PREPARATION EXAMPLE 46-2 In the same manner as in Preparation Example 31-2, 3,5-dichloro-2-(hydroxymethyl)pyridine was obtained as a colorless solid (1.43 g) from ethyl 3,5-dichloropyridine-2-carboxylate (2.0 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With 1,10-Phenanthroline; caesium carbonate;copper(l) iodide; In toluene; at 105℃; for 16.0h;Inert atmosphere; | a) 3,5-Dichloro-2-((2-chloropyridin-4-yloxy)methyl)pyridine <strong>[275383-87-4](3,5-Dichloropyridin-2-yl)methanol</strong> (2.00 g, 10.4 mmol), 2-chloro-4-iodopyridine (2.49 g, 10.4 mmol), cesium carbonate (4.41 g, 13.5 mmol), CuI (1.97 g, 10.4 mmol) and 1,10-phenanthroline (374 mg, 2.08 mmol) were stirred in toluene (20 mL) and degassed with a nitrogen stream for 10 minutes. The mixture was heated to 105° C. for 16 h, allowed to cool and filtered through a silica plug eluding with ethyl acetate. The filtrate was concentrated, and the resulting residue was purified by column chromatography (80 g ISCO column column eluding with ethyl acetate/hexanes; gradient 100percent hexanes to 40percent ethyl acetate) to provide the title compound (1.15 g, 38percent) as an orange solid: 1H NMR (300 MHz, CDCl3) delta 8.50 (d, J=2.1 Hz, 1H), 8.21 (d, J=5.8 Hz, 1H), 7.80 (d, J=2.1 Hz, 1H), 6.97 (d, J=2.2 Hz, 1H), 6.88-6.85 (dd, J=5.8, 2.2 Hz, 1H), 5.31 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9% | With thionyl chloride;N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 2.0h; | 3,5-dichloro-2-(chloromethyl)pyridine; [00376] To a 0 °C solution of 5-chloropicolinic acid (5.00 g, 26.0 mmol) and N,N- dimethylformamide (1 drop) in dichloromethane (20 mL) was added oxalyl chloride (3.28 g, 26.0 mmol) dropwise, after which the reaction mixture was allowed to warm up to room temperature and stirred at that temperature for two hours. The reaction was then cooled again to 0 °C, after which methanol (10 mL) was added dropwise to the reaction mixture, and the reaction was allowed to stir at room temperature for one hour where it was shown as complete by LCMS analysis. The reaction mixture was washed with saturated sodium bicarbonate solution, dried (magnesium sulfate), filtered and concentrated to afford methyl 3,5-dichloropyridine-2-carboxylate (5.36 g, 26.0 mmol, 100percent yield ) as a white solid.[00377] To a 0 °C solution of methyl 3,5-dichloropyridine-2-carboxylate (5.00 g, 24.3 mmol) in methanol (40 mL) was added sodium borohydride (1.80 g, 48.5 mmol), after which the reaction was warmed to room temperature and stirred at that temperature for two hours. The reaction mixture was then quenched by the addition of water (5 mL), concentrated to a residue, reconstituted in water (60 mL), extracted with ethyl acetate (2 x 60 mL), dried (magnesium sulfate), filtered and concentrated to afford (3,5-dichloropyridin-2-yl)methanol (2.90 g, 16.3 mmol, 67percent yield ) as a viscous oil. This material was used in the subsequent step without any purification.[00378] To a 0 °C solution of (3,5-dichloropyridin-2-yl)methanol (2.90 g, 16.3 mmol) in dichloromethane (50 mL) was added thionyl chloride (2.31 g, 19.6 mmol) dropwise, after which the reaction mixture was allowed to warm up to room temperature and stirred at that temperature for two hours. The reaction mixture was washed by the addition of saturated sodium bicarbonate solution (1 x 40 mL) and the organic layer was separated, dried (sodium sulfate), filtered and concentrated to a residue. Purification was achieved by silica gel chromatography using 9percent ethyl acetate in hexanes to afford 3,5-dichloro-2- (chloromethyl)pyridine (2.40 g, 12.2 mmol, 75percent yield) as an off-white solid. NMR (300 MHz, CDC13) delta (ppm): 8.36 (s, 1H), 7.56 (s, 1H), 4.66 (s, 2H). |
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