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CAS No. : | 53491-80-8 | MDL No. : | MFCD13193485 |
Formula : | C10H5ClN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FMQOMPVZLLUVOD-UHFFFAOYSA-N |
M.W : | 188.61 | Pubchem ID : | 13126946 |
Synonyms : |
|
Num. heavy atoms : | 13 |
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 : | 51.47 |
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) : | -5.48 cm/s |
Log Po/w (iLOGP) : | 1.9 |
Log Po/w (XLOGP3) : | 2.78 |
Log Po/w (WLOGP) : | 2.76 |
Log Po/w (MLOGP) : | 1.7 |
Log Po/w (SILICOS-IT) : | 3.04 |
Consensus Log Po/w : | 2.44 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.33 |
Solubility : | 0.0882 mg/ml ; 0.000468 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.21 |
Solubility : | 0.117 mg/ml ; 0.000622 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.4 |
Solubility : | 0.00744 mg/ml ; 0.0000394 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.74 |
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 |
---|---|---|
(2) The above-mentioned compound (916 mg) was dissolved in phosphorus oxychloride (10 mL), and the mixture was stirred at 70C for 5 hr with heating. Phosphorus oxychloride was evaporated under reduced pressure, and saturated aqueous sodium hydrogencarbonate solution was added to the residue. The mixture was extracted with ethyl acetate, and the extract was washed with brine, dried and concentrated under reduced pressure. The residue was purified by silica gel chromatography to give 1-chloro-4-cyanoisoquinoline (704 mg) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | at 140.0℃; for 2.0h; | 1-Chloro-4-cyanoisoquinoline (500 mg, 2.65 mmol) was added to piperazine (4.61 g, 53.5 mmol) at 140 C. The mixture was stirred at 140 C for 2 h, and then water was added to the reaction mixture. The mixture was extracted with chloroform, and the extract was washed with brine, dried and concentrated under reduced pressure to give 1-(4-cyanoisoquinolin-1-yl)piperazine (491 mg, 78%) as a dark brown solid. 1H NMR (300 MHz, CDCl3): delta 3.08-3.17 (4H, m), 3.62-3.68 (4H, m), 7.59 (1H, t, J = 7.1 Hz), 7.77 (1H, t, J = 7.1 Hz), 8.02-8.09 (2H, m), 8.47 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; at 95.0℃; for 2.0h;Inert atmosphere; | 100mL three-necked flask under nitrogen atmosphere, <strong>[53491-80-8]1-chloroisoquinoline-4-carbonitrile</strong> (45mg, 2.39mmol) was dissolved in toluene (30mL) and water (3mL) was added 4-chloro-3-( 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (687 mg, 2.87mmol), sodium carbonate (761mg, 7.18mmol), palladium catalyst tetrakis ( triphenylphosphine) palladium (0) (138mg, 0.12 mmol), then the reaction temperature was raised to 95 deg.C for 2 hours. The reaction solution was cooled, was added 50mL of ice water to quench the reaction, extracted with ethyl acetate (100mL, 3 times), saturated brine backwash (100mL, 3 times), dried over anhydrous sodium sulfate spin column chromatography (petroleum ether / ethyl acetate = 10: 1 ~ petroleum ether / ethyl acetate / dichloromethane = 1: 1: 1) to give an off-white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 95.0℃; for 12.0h;Inert atmosphere; | A 50 ml flask was charged with <strong>[53491-80-8]1-chloro-4-cyanoisoquinoline</strong> (300 mg, 1.59 mmol),Phenylboronic acid (290mg, 2.39mmol),Potassium carbonate (439mg, 3.18mmol),Tetratriphenylphosphine palladium (Pd (PPh3) 4) (184mg, 0.16mmol),Add 5ml toluene, 0.75ml ethanol and 2.5ml water under nitrogen protection, and react at 95 for 12 hours;Then it was cooled to room temperature, extracted with ethyl acetate, and then purified by rotary distillation (ethyl acetate / petroleum ether = 1/8, v / v).241 mg of product was obtained with a yield = 66%. |
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