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CAS No. : | 88312-64-5 | MDL No. : | MFCD19441225 |
Formula : | C7H7N3O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OUMPFIBIUJBCAH-UHFFFAOYSA-N |
M.W : | 197.15 | Pubchem ID : | 13063488 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 48.74 |
TPSA : | 111.03 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.98 cm/s |
Log Po/w (iLOGP) : | 0.8 |
Log Po/w (XLOGP3) : | 0.74 |
Log Po/w (WLOGP) : | 0.37 |
Log Po/w (MLOGP) : | -0.82 |
Log Po/w (SILICOS-IT) : | -1.6 |
Consensus Log Po/w : | -0.11 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.65 |
Solubility : | 4.44 mg/ml ; 0.0225 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.65 |
Solubility : | 0.441 mg/ml ; 0.00223 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.13 |
Solubility : | 14.7 mg/ml ; 0.0745 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.1 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
82% | at 0 - 20℃; for 2 h; Inert atmosphere | Concentrated nitric acid (65percent, 3.2 mmol, 76 mmol, 1.05 equiv) was added dropwise to a stirred suspension of 21 (10.0 g, 72.4 mmol) in concentrated sulfuric acid (96percent, 90.5 mL, 1.69 mol, 23.3 equiv) maintained at 0 C.The solution was brought back to room temperature and stirred for 2 h. The brown mixture was poured onto iced water and carefully quenched by adding solid Na2CO3 portionwise until complete neutralization (pH>8). The aqueous layerwas extracted three times with AcOEt. The combined organic layers were washed with brine and water, and dried over MgSO4. Evaporation of the residue in vacuo furnished the title compound 22 in analytically pure form(11.7 g, 82percent) as a colourless solid |
68% | at 0 - 70℃; for 23.75 h; | A solution of 2-amino-3-nicotinic acid methyl ester (4 g, 26 mmol) in a mixture of concentrated HN03 (2.8 mL) and H2S04 (10 mL) was stirred for 45 min at 0 °C, followed by room temperature for 19 h, and at 70 °C for 4 h. The reaction mixture was cooled to 0 °C and a saturated aqueous solution of NaHC03 (40 mL) was added till basic (pH 8). Extraction with EtOAc (3X40 mL), filtered and concentration of the combined organics afforded the title compound (3.5 g, 68percent) which was used in the next step without further purification. 1H NMR (DMSO-cfe, 400 MHz): δ 9.05 (1 H, d, J = 2.8 Hz), 8.69 (1 H, d, J = 2.8 Hz), 8.64 (1 H brs), 8.15 (1 H, brs), 3.88 (3H, s). MS: mlz 198 (M+1)+. |
35% | Stage #1: at 0 - 70℃; for 23.66 h; Stage #2: With sodium hydrogencarbonate In water at 0℃; |
Preparation Example A-3 2-Amino-5-nitro-nicotinic acid methyl ester 2-Amino-nicotinic acid methyl ester (1.00g, 6.57mmol) described in Preparation Example A-2 was dissolved at 0°C in a mixed solution of nitric acid (0.7mL) and sulfuric acid (2.6mL), which was stirred at 0°C for 40 minute and at room temperature for 19 hours, then, further stirred at 70°C for 4 hours. A saturated aqueous solution of sodium bicarbonate was added to the reaction solution at 0°C, which was extracted with ethyl acetate and tetrahydrofuran, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo. Methanol was added to the residue, the precipitated solid was filtered to obtain the title compound (459mg, 2.33mmol, 35percent) as a white solid. 1H-NMR Spectrum (DMSO-d6) δ (ppm): 3.86 (3H, s), 8.14 (1 H, brs), 8.62 (1 H, brs), 8.68 (1 H, d, J=2.7Hz), 9.04 (1 H, d, J=2.9Hz). |
35% | Stage #1: at 0 - 70℃; for 23.6667 h; Stage #2: With sodium hydrogencarbonate In water at 0℃; |
2-Amino-nicotinic acid methyl ester (1.00g, 6.57 mmol) described in Preparation Example A-2 was dissolved at 0°C in a mixed solution of nitric acid (0.7mL) and sulfuric acid (2.6mL), which was stirred at 0°C for 40 minute and at room temperature for 19 hours, then, further stirred at 70°C for 4 hours. A saturated aqueous solution of sodium bicarbonate was added to the reaction solution at 0°C, which was extracted with ethyl acetate and tetrahydrofuran, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo. Methanol was added to the residue, the precipitated solid was filtered to obtain the title compound (459mg, 2.33mmol, 35percent) as a white solid. 1H-NMR Spectrum (DMSO-d6) δ(ppm) : 3.86 (3H, s), 8.14 (1H, brs), 8.62 (1H, brs), 8.68 (1 H, d, J=2.7Hz), 9.04 (1 H, d, J=2.9Hz). |
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