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CAS No. : | 152803-24-2 | MDL No. : | MFCD11044307 |
Formula : | C6H4N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KAXIYYPIORYZLB-UHFFFAOYSA-N |
M.W : | 120.11 | Pubchem ID : | 15342142 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 30.97 |
TPSA : | 56.91 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) : | -6.88 cm/s |
Log Po/w (iLOGP) : | 0.79 |
Log Po/w (XLOGP3) : | 0.22 |
Log Po/w (WLOGP) : | 0.66 |
Log Po/w (MLOGP) : | -0.84 |
Log Po/w (SILICOS-IT) : | 0.86 |
Consensus Log Po/w : | 0.34 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.22 |
Solubility : | 7.29 mg/ml ; 0.0607 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.97 |
Solubility : | 12.7 mg/ml ; 0.106 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.49 |
Solubility : | 3.91 mg/ml ; 0.0326 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.4 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-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 |
---|---|---|
95% | at 200℃; for 2 h; | A mixture of lg of 5-methoxynicotinonitrile (7.46 mmol) and 8.62 g of pyridine hydrochloride is heated at 200°C for 2 hours. The crude reaction product is diluted in a water fraction several times with diethyl ether. The aqueous phase is basified by adding sodium bicarbonate and then extracted again with diethyl ether. The organic phase is dried and then concentrated to yield 850 mg of 5-hydroxynicotinonitrile (95percent) in the form of a beige solid.LCMS: m/z 120,94 (M+H+).1H MR: δΗ ppm (400 MHz, DMSO): 10,79 (s, 1H), 8,46 (s, 1H, CHarom.), 8,42 (s, 1H, CHarom.), 7,60 (s, 1H, CHarom.). |
95% | With pyridine hydrochloride In water at 200℃; for 2 h; | Example 11a 5-hydroxynicotinonitrile A mixture of 1 g of 5-methoxynicotinonitrile (7.46 mmol) and 8.62 g of pyridine hydrochloride is heated at 200° C. for 2 hours. The crude reaction product is diluted in a water fraction several times with diethyl ether. The aqueous phase is basified by adding sodium bicarbonate and then extracted again with diethyl ether. The organic phase is dried and then concentrated to yield 850 mg of 5-hydroxynicotinonitrile (95percent) in the form of a beige solid. LCMS: m/z 120.94 (M+H+). 1H NMR: δH ppm (400 MHz, DMSO): 10.79 (s, 1H), 8.46 (s, 1H, CHarom.), 8.42 (s, 1H, CHarom.), 7.60 (s, 1H, CHarom.). |
95% | at 200℃; for 2 h; | A mixture of 1g of 5-methoxynicotinonitrile (7.46 mmol) and 8.62 g of pyridine hydrochloride is heated at 200°C for 2 hours. The crude reaction product is diluted in a water fraction several times with diethyl ether. The aqueous phase is basified by adding sodium bicarbonate and then extracted again with diethyl ether. The organic phase is dried and then concentrated to yield 850 mg of 5-hydroxynicotinonitrile (95percent) in the form of a beige solid. LCMS: m/z 120,94 (M+H+). 1H NMR: δH ppm (400 MHz, DMSO): 10,79 (s, 1H), 8,46 (s, 1H, CHarom.), 8,42 (s, 1H, CHarom.), 7,60 (s, 1H, CHarom.) |
95% | at 200℃; for 2 h; | Example 11a: 5-hydroxynicotinonitrile A mixture of lg of 5-methoxynicotinonitrile (7.46 mmol) and 8.62 g of pyridine hydrochloride is heated at 200°C for 2 hours. The crude reaction product is diluted in a water fraction several times with diethyl ether. The aqueous phase is basified by adding sodium bicarbonate and then extracted again with diethyl ether. The organic phase is dried and then concentrated to yield 850 mg of 5-hydroxynicotinonitrile (95percent) in the form of a beige solid. LCMS: m/z 120.94 (M+H+). 1H NMR: δΗ ppm (400 MHz, DMSO): 10.79 (s, 1H), 8.46 (s, 1H, CHarom.), 8.42 (s, 1H, CHarom.), 7.60 (s, 1H, CHarom.). |
95% | at 200℃; for 2 h; | Example 11a: 5-hydroxynicotinonitrile A mixture of lg of 5-methoxynicotinonitrile (7.46 mmol) and 8.62 g of pyridine hydrochloride is heated at 200°C for 2 hours. The crude reaction product is diluted in a water fraction several times with diethyl ether. The aqueous phase is basified by adding sodium bicarbonate and then extracted again with diethyl ether. The organic phase is dried and then concentrated to yield 850 mg of 5-hydroxynicotinonitrile (95percent) in the form of a beige solid. LCMS: m/z 120.94 (M+H+). 1H NMR: δΗ ppm (400 MHz, DMSO): 10.79 (s, 1H), 8.46 (s, 1H, CHarom.), 8.42 (s, 1H, CHarom.), 7.60 (s, 1H, CHarom.). |
95% | at 200℃; for 2 h; | A mixture of 1g of 5-methoxynicotinonitrile (7.46 mmol) and 8.62 g of pyridine hydrochloride is heated at 200°C for 2 hours. The crude reaction product is diluted in a water fraction several times with diethyl ether. The aqueous phase is basified by adding sodium bicarbonate and then extracted again with diethyl ether. The organic phase is dried and then concentrated to yield 850 mg of 5-hydroxynicotinonitrile (95percent) in the form of a beige solid. LCMS: m/z 120,94 (M+H+). 1H NMR: δH ppm (400 MHz, DMSO): 10,79 (s, 1H), 8,46 (s, 1H, CHarom.), 8,42 (s, 1H, CHarom.), 7,60 (s, 1H, CHarom.) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With hydrazine hydrate; caesium carbonate In water at 120℃; for 16 h; | 25 mL of the reaction flask was added hydrazine hydrate (0.25 mmol)5-Cyano-pyridine-3-boronic acid pinacol ester (0.5mmol),Cesium carbonate (1.0 mmol),Water (2.5 mmol)And polyethylene glycol-2000 (2.0 g).The reaction mixture was reacted at 120 ° C until the reaction was complete.The reaction mixture was cooled to room temperature,The product was isolated by column chromatography after evaporation of the solvent under reduced pressure,Yield 85percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | Stage #1: at 135℃; for 5 h; Stage #2: With ammonium hydroxide In water at 0℃; for 1 h; |
5-Hydroxy-nicotinonitrile (2) (1199) A mixture of 5-bromo-pyridin-3-ol (9.94 mL, 54.0 mmol) and CuCN (7.4 g, 82.62 mmol) in DMF (20 mL) was heated at 135° C. for 5 hour. DMF was removed under reduced pressure, the residue was diluted with NH4OH (10 mL) at 0° C. The mixture was bubbled with ammonia gas for 1 hour, cooled to 0° C. and acidified with conc. HCl (35 mL) until pH reached to 4. The resulting mixture was extracted with EtOAc (5×100 mL). The organic layer was washed with water (2×100 mL) and brine (2×100 mL) solution, dried over anhydrous Na2SO4, filtered, and concentrated to give yellow solid. Purification was accomplished by flash chromatography on silica gel using 5-25percent EtOAc/hexanes gradient elution to yield the title compound (2.5 g, 39percent) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.78 (s, 1H), 8.46 (d, J=2.0 Hz, 1H), 8.41 (d, J=2.7 Hz, 1H), 7.61-7.57 (m, 1H). |
[ 1256835-79-6 ]
6-Chloro-5-methoxynicotinonitrile
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