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CAS No. : | 125104-34-9 | MDL No. : | MFCD14582033 |
Formula : | C8H7NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FLXVRBSKKVMMQQ-UHFFFAOYSA-N |
M.W : | 165.15 | Pubchem ID : | 19744506 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 40.9 |
TPSA : | 56.26 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) : | -6.95 cm/s |
Log Po/w (iLOGP) : | 1.11 |
Log Po/w (XLOGP3) : | 0.5 |
Log Po/w (WLOGP) : | 0.68 |
Log Po/w (MLOGP) : | -0.28 |
Log Po/w (SILICOS-IT) : | 1.35 |
Consensus Log Po/w : | 0.67 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.35 |
Solubility : | 7.36 mg/ml ; 0.0446 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.25 |
Solubility : | 9.25 mg/ml ; 0.056 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.04 |
Solubility : | 1.5 mg/ml ; 0.0091 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.4 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | 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 |
---|---|---|
85% | Stage #1: With Dess-Martin periodane In dichloromethane at 20℃; for 2.5 h; Stage #2: With sodium hydrogencarbonate In dichloromethane; water at 20℃; for 0.25 h; |
Methyl 2-(hydroxymethyl)isonicotinate (8.36 g, 50 mmol) (from reference compound 38, step 1) was dissolved in dichloromethane (150 mL). Dess-Martin periodinane (25 g, 58.94 mmol) was added and the mixture stirred at room temperature for 2 h 30 min. Sodium sulfothioate (59.3 g, 375.00 mmol) was dissolved in satd NaHCO3 and added to the reaction mixture. The suspension was vigorously stirred at room temperature for 15 min, DCM was added and the phases were separated. The aqueous phase was extracted with DCM twice and the combined organic layers were dried over MgSO4 and evaporated. The residue was purified by automated flash chromatography on a Biotage.(R). KP-SIL 340 g column. Gradient heptanes/EtOAc 80:20 to 65:35 over 5 CV was used as mobile phase. Methyl 2-formylisonicotinate (7 g, 85percent) was isolated as an off-white solid. 1H NMR (400 MHz, cdcl3) δ 4.00 (s, 3H), 8.09 (dd, 1H), 8.49 (s, 1H), 8.95 (d, 1H), 10.15 (s, 1H). MS m/z 165 (M)+ |
85% | With Dess-Martin periodane In dichloromethane at 20℃; for 2.5 h; | Methyl 2-(hydroxymethyl)isonicotinate (8.36 g, 50 mmol) was dissolved in dichloromethane (150 ml_). Dess-Martin periodinane (25 g, 58.94 mmol) was added and the mixture stirred at room temperature for 2 h 30 min. Sodium sulfothioate (59.3 g, 375.00 mmol) was dissolved in satd NaHCO3 and added to the reaction mixture. The suspension was vigorously stirred at room temperature for 15 min, DCM was added and the phases were separated. The aqueous phase was extracted with DCM twice and the combined organic layers were dried over MgSO and evaporated. The residue was purified by automated flash chromatography on a Biotage.(R). KP-SIL 340g column. Gradient heptanes / EtOAc 80:20 to 65:35 over 5 CV was used as mobile phase. Methyl 2-formylisonicotinate (7 g, 85 percent) was isolated as an off-white solid. 1H NMR (400 MHz, cdcl3) δ 4.00 (s, 3H), 8.09 (dd, 1 H), 8.49 (s, 1 H), 8.95 (d, 1 H), 10.15 (s, 1 H). MS m/z 165 (M+H)+ |
72% | With manganese(IV) oxide In dichloromethane at 20℃; | A. methyl 2-formylpyridine-4-carboxylate To a solution of methyl 2-(hydroxymethyl)pyridine-4-carboxylate (30 g, 179.64 mmol) in DCM (1 L) was added MnO2 (93.77 g. 1.0778 mol) at r.t. and stirred overnight. The reaction mixture was then filtered and concentrated to afford the title compound (21.3 g, 72percent). [M+H] Calc'd for C8H7NO3, 166. Found, 166. |
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