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CAS No. : | 106726-82-3 | MDL No. : | MFCD07367902 |
Formula : | C8H6N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RLUVYUFWNPLVPL-UHFFFAOYSA-N |
M.W : | 162.15 | Pubchem ID : | 13623673 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 40.23 |
TPSA : | 62.98 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) : | -6.99 cm/s |
Log Po/w (iLOGP) : | 1.51 |
Log Po/w (XLOGP3) : | 0.42 |
Log Po/w (WLOGP) : | 0.74 |
Log Po/w (MLOGP) : | -0.28 |
Log Po/w (SILICOS-IT) : | 1.17 |
Consensus Log Po/w : | 0.71 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.35 |
Solubility : | 7.28 mg/ml ; 0.0449 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.31 |
Solubility : | 7.95 mg/ml ; 0.049 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.18 |
Solubility : | 1.08 mg/ml ; 0.00665 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.69 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
60% | at 160℃; for 12 h; Inert atmosphere | CuCN (5.22 g, 58.3 mmol) was added to a solution of methyl 5-bromonicotinate (6 g, 27.8 mmol) in dry DMF (150 mL). The solution was purged with argon and heated to 160 °C for 12 h under argon atmosphere. The reaction mixture was cooled to room temperature and then quenched with saturated NH4Cl solution. Further EtOAc was added and the reaction mixture was stirred for 10 min. The reaction mixture was filtered through a Celite plug, the organic layer was separated, washed with water and brine, and dried over anhydrous Na2SO4. Solvent was evaporated under reduced pressure to get methyl-5-cyano-nicotinate as greenish-white solid (2.7g, yield 60percent): 1H NMR (300 MHz, DMSO-d6) δ 9.29-9.27 (m, 2H), 8.77 (s, 1H), 3.91 (s, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30.9% | for 15 h; Heating / reflux | Preparation 66 ;5-Cyano-nicotinic acid methyl ester; Reflux a solution of methyl 5-bromonicotinate (2.16 g, 10.0 mmol, 1 equiv) and copper (I) cyanide (1.79 g, 20.0 mmol, 2.0 equiv) in anhydr DMF (10 mL) for 15 h. After allowing to cool, filter the reaction mixture through Celite rinse with EtOAc (100 mL). A black precipitate forms in the filtrate. Wash the filtrate with salted H20 (3 x 100 mL). Dry the organic layer (anhydr Na2S04) and rotary evaporate (40 °C) giving 546 mg (33.7percent) of product as a light-yellow solid. Transfer this material to a column of silica gel (80 mm x 20 mm dia. ) and elute (20-35percent EtOAc/hex) to yield 501 mg (30.9percent) of 5- cyano-nicotinic acid methyl ester as an off-white solid. MS (m/e): 163.07 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11% | Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at -78℃; for 1.05 h; Stage #2: With sodium hydroxide; water In tetrahydrofuran |
Preparation 67; 5-Hydroxymethyl-nicotinonitrile; Add lithium aluminum hydride (l. OM in THF ; 1. 5mL, 1. 5mmol, 0. 5equiv) over a period of 3min to a solution of 5-cyano-nicotinic acid methyl ester (479mg, 2. 95mmol, lequiv) in anhydr THF (15mL) and cool to-78°C. After lh while still at-78°C, quench the reaction with H20 (60, uL), 5M aq NaOH (60pL), and more H20 (180μL). Filter the reaction mixture through paper. Rotary evaporate the filtrate (40°C) to give 369mg of material as a yellow solid. Transfer this material to a column of silica gel (130mm x 25mmdia. ) and elute (2percent MeOH/CH2Cl2) to yield 180mg of a mixture of ester, hemiacetal, and aldehyde as a yellow solid and 45mg (11percent) of 5-hydroxymethyl- nicotinonitrile as a yellow solid. MS (m/e) : 163.07 (M+1). |
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