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CAS No. : | 2973-27-5 | MDL No. : | MFCD00972111 |
Formula : | C10H6N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JBSAUEMFOKUWTP-UHFFFAOYSA-N |
M.W : | 154.17 | Pubchem ID : | 270566 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 46.46 |
TPSA : | 36.68 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.83 cm/s |
Log Po/w (iLOGP) : | 1.68 |
Log Po/w (XLOGP3) : | 1.98 |
Log Po/w (WLOGP) : | 2.11 |
Log Po/w (MLOGP) : | 1.14 |
Log Po/w (SILICOS-IT) : | 2.44 |
Consensus Log Po/w : | 1.87 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.66 |
Solubility : | 0.337 mg/ml ; 0.00219 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.38 |
Solubility : | 0.648 mg/ml ; 0.00421 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.77 |
Solubility : | 0.0261 mg/ml ; 0.000169 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.38 |
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 |
---|---|---|
94% | With ammonium acetate; phenyltrimethylammonium tribromide In acetonitrile at 20℃; for 17 h; | General procedure: to a solution of 2-pyridinecarbaldehyde 1 (54 mg, 0.5 mmol) and ammonium acetate (385mg, 5.0 mmol) in MeCN )6ml), was added trimethylphenylammonium tribromide (376 mg, 1.0 mmol) at room temperature. after stirring for 21 h at rt, the reaction mixture was treated with 0.5 M aq Na2S2O3(10 ml), 1.0 M NaHCO3 )15 ml) and extracted with EtOAc (60 mL). The organic layer was washed with 0.5 M Na2S2O3 and successively washed with saturated aq.NaCl, and dried over MgSO4. |
50.5% | Stage #1: With sodium bromate; ammonia In water at 90℃; for 2 h; Stage #2: With sodium hydrogencarbonate In water; ethyl acetate |
Example 4: Production of 4-quinolinecarbonitrile Into a 15 ml, test tube-shaped reactor equipped with a magnetic stirrer and a reflux condenser were added 0.71 g (4.5 mmol) of 4-quinolinecarboaldehyde, 0.27 g (1.8 mmol) of sodium bromate, 0.6 g (10 mmol) of acetic acid, 0.35 g (5 mmol) of 25percent aqueous ammonia and 1 ml of water, followed by stirring at 90°C for 2 hours. The reaction mixture contained, as a component, 97.4percent (in terms of areal ratio of gas chromatography) of 4-quinolinecarbonitrile. To the reaction mixture were added 30 ml of a saturated aqueous sodium bicarbonate solution and 30 ml of ethyl acetate. The mixture was subjected to phase separation. Then, there were conducted washing with a saturated aqueous sodium chloride solution, drying over anhydrous sodium sulfate, and distillation under reduced pressure for ethyl acetate removal. The residue was purified by silica gel column chromatography (ethyl acetate/n-hexane = 1:1 v/v) to obtain 0.35 g (yield: 50.5percent) of white crystals. Gas mass chromatography was conducted to confirm a molecular ion peak [M+] of 154. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8.03 g | at 180℃; for 3 h; Inert atmosphere | Step A: Preparation of 4-cyanoquinolineTo a solution of N-methylpyrrolidinone (100 mL) and CuCN (21.5 g, 240 mmol) was added 4-bromoquinoline (25.0 g, 120 mmol) in one portion with vigorous stirring under nitrogen. The reaction was heated to 180 °C for 3 hours. The reaction mixture was allowed to cool, and then added to water (300 mL). The crude solid product was filtered and dried in a vacuum oven overnight to give the title product (8.03 g).‘HNMR(CDC13) ö 7.73-7.81 (m, 2 H) 7.89 (ddd, J=8.47, 7.01, 1.34 Hz, 1 H) 8.11-8.34 (m,2 H) 9.06 (d, J4.39 Hz, 1 H). |
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