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CAS No. : | 24059-89-0 | MDL No. : | MFCD07374875 |
Formula : | C7H6N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BEETZOYEGNNBAS-UHFFFAOYSA-N |
M.W : | 134.14 | Pubchem ID : | 11332493 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 35.44 |
TPSA : | 45.91 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) : | -6.49 cm/s |
Log Po/w (iLOGP) : | 1.53 |
Log Po/w (XLOGP3) : | 0.88 |
Log Po/w (WLOGP) : | 0.96 |
Log Po/w (MLOGP) : | -0.48 |
Log Po/w (SILICOS-IT) : | 1.3 |
Consensus Log Po/w : | 0.84 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.6 |
Solubility : | 3.34 mg/ml ; 0.0249 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.43 |
Solubility : | 5.0 mg/ml ; 0.0373 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.21 |
Solubility : | 0.837 mg/ml ; 0.00624 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.77 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
88% | at 4 - 25℃; for 2 h; Inert atmosphere | Sodium methoxide (0.41 g, 7.5 mmol) was dissolved in 10 mL anhydrous N,N-dimethylformamide in a 25 mL round bottom flask under a nitrogen atmosphere and cooled to 4 °C with an ice water bath. 3-Chloro-2-cyanopyridine (1.01 g, 7.2 mmol) was added, the ice water bath was removed, and the reaction was warmed to 25 °C . After 2 hours, the reaction was concentrated under vacuum and ethyl acetate was added to the residue and the mixture was filtered to remove the precipitate. The resulting filtrate was then concentrated on a rotary evaporator to obtain the desired product as a white solid that was used without further purification (0.88g, 88percent yield). 1H-NMR(CDCl3) δ 8.22 (dd, J = 7.4 and 1.6Hz, 1H), 7.90 (dd, J = 7.5 and 7.3 Hz, 1H), 7.73 (dd, J = 7.73 and 1.6 Hz, 1H),3.92 (s, 3H). (ESI+): m/z (M+H)+ = 135. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.1 g | With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); zinc In N,N-dimethyl acetamide at 140℃; for 3 h; Inert atmosphere; Microwave irradiation | Step a. A solution of 2-bromo-3-methoxypyridine (CAS Number 24100-18-3) (3.0 g, 16.04 mmol) in DMA (10 ml) was degassed at rt for 15 min before addition of zinc dust (0.209 g, 3.20 mmol), Zn(CN)2 (1.50 g, 12.83 mmol), Pd2(dba)3 (0.29 g, 0.320 mmol) and 1, 1'- bis(diphenylphosphino)ferrocene (0.36 g, 0.64 mmol) at rt. The reaction mixture was heated in microwave at 140°C for 3 h. The resulting reaction mixture was cooled to rt and poured into water (200 ml). The obtained mixture was extracted with EtOAc (4 x 100 ml). The combined organic phase was dried over Na2S04, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography (28percent EtOAc in hexane) yielding 3-methoxypicolinonitrile (2.1 g, 15.6 mmol). LCMS: Method C, 1.65 min, MS: ES+ 135.04; NMR (400 MHz, DMSO-d6) δ ppm 8.31 (d, J =4.4 Hz, 1 H), 7.73 - 7.80 (m, 2 H), 3.97 (s, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | at 0℃; for 2 h; Inert atmosphere | 3-Methoxy-2-cyanopyridine (0.88 g, 6.5 mmol) was dissolved in anhydrous tetrahydrofuran (20 mL) in a 3-neck flask under a nitrogen atmosphere.The reaction was cooled to 0 °C, and a solution of methylmagnesium iodide in tetrahydrofuran (3M, 4.3 ml, 12.8mmol) was added. The reaction was stirred at 0 °C for 2 hours and then quenched with 50 mL of water at 0 °C. The pH was adjusted to 7 with 2N HCl, and the resulting solution was extracted with ethyl acetate (3 x 50 mL)), the combined organic layers were dried over anhydrous sodium sulfate and concentrated on a rotary evaporator to provide the crude product. Silica gel chromatography (gradient of 0 – 100percent ethyl acetate in hexane) provided the product as a colorless oil (0.79g, 79percent yield). 1H-NMR (CDCl3) δ 8.42 (dd, J = 7.7 and 1.4Hz, 1H), 7.63 (dd, J = 7.6 and 1.4 Hz, 1H), 7.61 (dd, J = 7.7 and 7.6 Hz, 1H),3.82 (s, 3H), 2.14 (s, 3H), (ESI+): m/z (M+H)+= 152. |
0.79 g | at 0℃; for 2 h; Inert atmosphere | 3-Methoxy-2-cyanopyridine (0.88g, 6.5mmol) was dissolved in anhydrous tetrahydrofuran (20 mL) in a 3-neck flask under a nitrogen atmosphere. The reaction was cooled to 0 °C, and a solution of methyl magnesium iodide in tetrahydrofuran (3M, 4.3 ml, 12.8mmol) was added. The reaction was stirred at 0 °C for 2 hours and then quenched with 50 mL of water at 0 °C. The pH was adjusted to 7 with 2N HC1, and the resulting solution was extracted with ethyl acetate (3 x 50 mL)), the combined organic layers were dried over anhydrous sodium sulfate and concentrated on a rotary evaporator to provide the crude product. Silica gel chromatography (ISCO RediSep 80 gram column, gradient of 0 - 100percent ethyl acetate in hexane over 26 minutes) provided the product as a colorless oil (0.79g, 79percent yield). 1H-NMR (400Mz, CDCI3) δ 8.42 (1H, dd, J = 7.7 and 1.4 Hz), 7.63 (1H, dd, J = 7.6 and 1.4 Hz), 7.61 (1H, dd, J = 7.7 and 7.6 Hz), 3.82 (3H, s), 2.14 (3H, s). Ms (M+H): 152. |
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