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CAS No. : | 499-81-0 | MDL No. : | MFCD00006393 |
Formula : | C7H5NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MPFLRYZEEAQMLQ-UHFFFAOYSA-N |
M.W : | 167.12 | Pubchem ID : | 10366 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 38.16 |
TPSA : | 87.49 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) : | -7.39 cm/s |
Log Po/w (iLOGP) : | 0.21 |
Log Po/w (XLOGP3) : | -0.1 |
Log Po/w (WLOGP) : | 0.48 |
Log Po/w (MLOGP) : | -1.47 |
Log Po/w (SILICOS-IT) : | 0.12 |
Consensus Log Po/w : | -0.15 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.05 |
Solubility : | 14.9 mg/ml ; 0.0889 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.28 |
Solubility : | 8.68 mg/ml ; 0.0519 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.77 |
Solubility : | 28.7 mg/ml ; 0.172 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.22 |
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 |
---|---|---|
94% | for 18 h; Reflux | 2,6-Pyridine dicarboxylic acid (5.00 g, 29.92 mmol) was dissolved in MeOH (100 ml) and concentrated sulfuric acid (2 ml) was slowly added thereto and refluxed for 18 hours. After the reaction was completed, the solvent was removed under reduced pressure, and the mixture was extracted with sodium bicarbonate and dichloromethane. The dichloromethane layer was washed with a saturated sodium chloride aqueous solution to obtain 5.5 g (94percent) of compound l1 |
82% | at 50 - 65℃; | 4) To a mixture of pyridine-3,5-dicarboxylic acid (110 g, 0.66 mol) and methanol (660 mL) was added dropwise conc. sulfuric acid (226.0 g, 2.30 mol) at 50° C. or lower. Thereafter, the mixture was heated to 55-65° C. and stirred for 7 hr. The reaction mixture was allowed to cool to 40-50° C., and water (220 mL) was added. Furthermore, 5percent aqueous ammonia (about 1.10 L) was added dropwise at 40-50° C. to adjust the mixture to pH 8.0-8.5. After stirring at 40-50° C. for 30 min, the mixture was cooled to 0-10° C. and stirred for 1 hr. The precipitated crystals were collected by filtration, washed successively with methanol-water (1:3, 165 mL) and water (440 mL), and dried under reduced pressure at 50° C. to give dimethyl pyridine-3,5-dicarbonate as a white crystalline powder (105.0 g, yield 82.0percent). 1H-NMR (300 MHz, CDCl3) δ 4.00 (s, 6H), 8.87 (s, 1H), 9.37 (s, 2H). Anal. Calcd for C9H9NO4: C, 55.39; H, 4.65; N, 7.18; O, 32.79. Found: C, 55.42; H, 4.65; N, 7.16. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With thionyl chloride; sodium chloride; sodium hydrogencarbonate In methanol | [Step 1] Synthesis of dimethyl pyridine-3,5-dicarboxylate Pyridine-3,5-dicarboxylic acid (8.3 g) was suspended in anhydrous methanol (60 ml), and thionyl chloride (11 ml) was added dropwise at room temperature. The mixture was heated under reflux for 1.5 hours in an argon atmosphere and allowed to cool. The solvent was evaporated under reduced pressure, and extracted with water-ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain the title compound (7.5 g, 78percent). m.p.: 83.5-84.5° C. IR spectrum (KBr tab.) νcm-1: 1734, 1603, 1315, 1269, 1240, 995, 746. NMR spectrum (*DMSO-d6) δ ppm: 9.30 (2H, s), 8.66 (1H, s), 3.93 (6H, s). |