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CAS No. : | 89284-61-7 | MDL No. : | MFCD08234759 |
Formula : | C6H3ClN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QBKPXDUZFDINDV-UHFFFAOYSA-N |
M.W : | 138.55 | Pubchem ID : | 13411112 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 33.96 |
TPSA : | 36.68 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) : | -6.33 cm/s |
Log Po/w (iLOGP) : | 1.31 |
Log Po/w (XLOGP3) : | 1.15 |
Log Po/w (WLOGP) : | 1.61 |
Log Po/w (MLOGP) : | 0.4 |
Log Po/w (SILICOS-IT) : | 1.98 |
Consensus Log Po/w : | 1.29 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.92 |
Solubility : | 1.68 mg/ml ; 0.0121 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.51 |
Solubility : | 4.23 mg/ml ; 0.0306 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.7 |
Solubility : | 0.278 mg/ml ; 0.002 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.4 |
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 |
---|---|---|
86% | at 20℃; for 1 h; | Reference Example 11 4-methoxynicotinonitrile (21) To a solution of compound (20)(2.77 g, 20.0 mmol) in methanol (5 ml) was added a 28percent sodium methylate-methanol solution (5.0 g, 24.0 mmol) at room temperature and the mixture was stirred for one hr. The solvent was concentrated and the obtained residue was partitioned between ethyl acetate and iced-brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was recrystallized from a small amount of isopropyl ether to give the title compound (2.3 g, 86percent). 1H-NMR (200Hz, CDCl3) δ: 4.02 (3H, s), 6.93 (1H, d, J = 5.8 Hz), 8.65 (1H, d, J =5.8Hz), 8.69 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.89% | With triethylamine; trichlorophosphate In tetrahydrofuran at 0 - 20℃; for 3 h; | Step B: Preparation of 4-chloronicotinonitrile: 4-chloronicotinamide (2.7 g, 17.24 mmol) was suspended in cold (0° C.) THF (100 mL) and triethylamine (19.23 mL, 138.0 mmol). To this was slowly added phosphoryl trichloride (1.607 mL, 17.24 mmol). The reaction mixture was allowed to stir for 3 hours while warming to room temperature. Silica gel was added and the reaction mixture was concentrated (keeping the bath temperature ˜35° C.). The residue was dry loaded onto a Biotage 40M column and eluted with CH2Cl2 (100percent) to give 2.1 g (87.89percent yield) of the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | Stage #1: With tetrafluoroboric acid; sodium nitrite In ethanol; water at 0℃; for 0.5 h; Stage #2: With sodium cyanide In water; acetonitrile at 0 - 20℃; for 10 h; |
[Example 719] Compound q1 4-Chloropyridine-3-carbonitrile [1519] aqueous tetrafluoroboric acid solution (10 ml) was added to a solution of 4-chloropyridin-3-amine (1.29 g, 10.0 mmol) in ethanol (10 ml) at 0°C. An aqueous solution (10 ml) of sodium nitrite (725 mg, 10.5 mmol) was added to the resultant mixed solution at the same temperature, and it was stirred at the same temperature for 30 minutes. The precipitate was collected by filtration and washed with ethanol, and the resultant brown solid (1.94 g) was then dissolved in acetonitrile (10 ml). A mixed solution of sodium cyanide (980 mg, 20.0 mmol) and copper(I) cyanide (896 mg, 10.0 mmol) in water (10 ml) and acetonitrile (1 ml) was added to the resultant solution at 0°C, and it was stirred while gradually warming to room temperature for 10 hours. The reaction mixture was cooled to 0°C, after which a saturated aqueous solution of sodium bicarbonate was added, and it was stirred for five minutes. The resultant solution was extracted with ethyl acetate, and the organic layer was then washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, followed by concentration under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/n-hexane) to yield the title compound (605 mg, 44percent) as a pale yellow solid. 1H-NMR (300 MHz, CDCl3) δ: 8.87 (1H, s), 8.72 (1H, d, J = 3.9 Hz), 7.51 (1H, d, J = 3.9 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | Stage #1: With tetrafluoroboric acid; sodium nitrite In ethanol; water at 0℃; for 0.5 h; Stage #2: at 0 - 25℃; for 10 h; |
A 48percent aqueous tetrafluoroboric acid solution (10 ml) was added to a solution of 4-chloropyridin-3-amine (1.29 g, 10.0 mmol) in ethanol (10 ml) at 0°C. A solution of sodium nitrite (725 mg, 10.5 mmol) in water (10 ml) was added to the resultant mixed solution at the same temperature, and it was stirred at the same temperature for 30 minutes. The precipitate was collected by filtration and washed with ethanol, and the resultant brown solid (1.94 g) was then dissolved in acetonitrile (10 ml). A mixed solution of sodium cyanide (980 mg, 20.0 mmol) and copper(I) cyanide (896 mg, 10.0 mmol) in water (10 ml) and acetonitrile (1 ml) was added to the resultant solution at 0°C, and it was stirred while gradually warming to room temperature for 10 hours. The reaction mixture was cooled to 0°C, after which a saturated aqueous solution of sodium bicarbonate was added, and it was stirred for five minutes. The resultant solution was extracted with ethyl acetate, and the organic layer was then washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, followed by concentration under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/n-hexane) to yield the title compound (605 mg, 44percent) as a pale yellow solid. 1H-NMR (300 MHz, CDCl3) δ: 8.87 (1H, s), 8.72 (1H, d, J = 3.9 Hz), 7.51 (1H, d, J = 3.9 Hz). |
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