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CAS No. : | 34846-64-5 | MDL No. : | MFCD00006766 |
Formula : | C10H6N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QZZYYBQGTSGDPP-UHFFFAOYSA-N |
M.W : | 154.17 | Pubchem ID : | 93177 |
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) : | -6.13 cm/s |
Log Po/w (iLOGP) : | 1.65 |
Log Po/w (XLOGP3) : | 1.57 |
Log Po/w (WLOGP) : | 2.11 |
Log Po/w (MLOGP) : | 1.14 |
Log Po/w (SILICOS-IT) : | 2.44 |
Consensus Log Po/w : | 1.78 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.4 |
Solubility : | 0.611 mg/ml ; 0.00397 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.95 |
Solubility : | 1.73 mg/ml ; 0.0112 mol/l |
Class : | Very 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 : | 1.37 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-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 |
---|---|---|
With C40H45ClN3O2PRu; In methanol; water; at 20℃; for 4h;Inert atmosphere; Schlenk technique; Green chemistry;Catalytic behavior; | General procedure: Organic nitrile (1 mmol) and distilled water (1 mL) were sequentially added to 3 mL methanol solution of the [Ru-NHC] catalyst (0.5 mol%) and the reaction mixture was stirred at room temperature. The progress of the reaction in each case was monitored by TLC analysis. After completion of reaction the catalyst was extracted from the reaction mixture by the addition of CH2Cl2/petroleum ether followed by filtration. The filtrate was subjected to GC analysis and the product was identified with authentic samples. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; for 3h; | Quinoline-3-nitrile (1.0 g) was dissolved in diethyl ether (30 mL) and treated with lithium bis(trimethylsilyl)amide (1.0 M in THF, 13 mL). The reaction was stirred for 3 hours, then washed 3 times with 1 N HCl (50 mL). The combined aqueous washes were neutralized with 6 N NaOH and extracted 6 times with ethyl acetate (50 mL). The ethyl acetate extractions were dried over sodium sulfate and the solvent was evaporated to provide 0.63 g of quinoline-3-carboxamidine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | Example 4 2-(3-Quinolinyl)-4H-1,3-benzothiazine-4-one The titled compound was obtained by the reaction of methyl thiosalicylate (1.00 g, 5.9 mmol) and <strong>[34846-64-5]<strong>[34846-64-5]3-quinolinecarbonitril</strong>e</strong> (0.92 g, 6.0 mmol) in accordance with the method described in Example 1 (0.30 g, 17 %). mp. 216.0-217.0 C (recrystallized from chloroform-hexane) IR (KBr): 3045, 1657, 1591, 1572, 1518, 1458, 1439, 1292, 1236, 1097, 920, 738 cm-1.1H-NMR (CDCl3) delta: 7.59-7.73 (4H, m), 7.87 (1H, m), 8.00 (1H, d, J = 8.0 Hz), 8.20 (1H, d, J = 8.4 Hz), 8.58 (1H, dd, J = 1.3, 7.6 Hz), 9.02 (1H, d, J = 2.1 Hz), 9.64 (1H, d, J = 2.1 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
141 mg (25%) | With hydroxylamine; | a) Quinoline-3-amidoxime The title compound was prepared from 3-cyano-quinoline (464 mg, 3.01 mmol) and 50 wt % hydroxylamine (200 muL, 3.26 mmol) similar to Example 36c, and yielded 141 mg (25%) of light yellow solid. 1H NMR (DMSO-d6): 10.01 (s, 1H), 9.22 (d, J=1.93 Hz, 1H), 8.58 (d, J=1.64 Hz, 1H), 8.01 (dd, J=12.09, 8.24 Hz, 2H), 7.78 (td, J=7.63, 1.28 Hz, 1H), 7.65 (t, J=7.56 Hz, 1H), 6.11 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; palladium; | b 3(R,S)-Aminomethyl-1,2,3,4-tetrahydroquinoline A solution of 10 g of quinoline-3-carboxylic acid nitrile in 500 ml of ethanol is hydrogenated in the presence of 1.0 g of palladium-on-charcoal (10% of palladium) at 45 C. under normal pressure for 40 h: Rf (A)=0.61. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium methylate; acetic acid; In methanol; diethyl ether; | a) <strong>[34846-64-5]3-cyanoquinoline</strong> (1.58 g, 10.2 mmol) was dissolved in methanol (20 ml), and sodium methoxide (0.06 g, 1.1 mmol) was added. The reaction was conducted at room temperature for 22 hours. After the reaction was completed, acetic acid (0.07 g, 1.1 mmol) was added to neutralize the reaction solution, and the solution was concentrated under reduced pressure. Diethyl ether (60 ml) was added to the concentrated residue, and insolubles were removed by filtration. The filtrate was concentrated under reduced pressure to give the crude product of methyl 3-quinolinecarboximidate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With sulfuric acid; In benzene; at 80℃; for 1h; | Sulfuric acid (0.4 mL) and 1-(3-methylbenzyl)cyclohexanol (204 mg, 1.0 mmol) were added while cooling with ice to a benzene (1.0 mL) solution of quinoline-3-carbonitrile (154 mg, 1.0 mmol), and after stirring for 1 hour at 80C, the solution was poured into water followed by extraction with ethyl acetate and applying the resulting residue to chromatography to obtain 180 mg of the target compound (yield: 73%). Physical property: oil. 1H-NMR (270MHz, CDCl3) delta ppm: 1.51-1.85 (10H, m), 2.40 (3H, s), 2.81 (2H, s), 7.02-7.14 (3H, m), 7.57 (1H, t, J=8.4Hz), 7.75 (1H, t, J=8.4Hz), 7.86 (1H, d, J=8.4Hz), 8.15 (1H, d, J=8.4Hz), 8.36 (1H, s), 9.16 (1H, s). MS m/z: 340(M+), 325, 311, 297, 284, 244, 142, 128. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With trifluorormethanesulfonic acid; In 1,1-dichloroethane; at 20℃; for 18h; | Trifluoromethane sulfonic acid (0.52 mL) were added while cooling with ice to a dichloroethane (0.58 mL) solution of an about 4:7 mixture of 1-fluoro-(2-methylpropen-1-yl) benzene and 1-fluoro-(2-methylpropen-2-yl) benzene (87.3 mg, 0.58 mmol) and quinoline-3-carbonitrile (89.6 mg, 0.58 mmol), and after stirring for 18 hours at room temperature, the solution was poured into water followed by extraction with ethyl acetate and applying the resulting residue to chromatography to obtain 82.2 mg of the target compound (yield: 47%). Melting point: 97-100C 1H-NMR (500MHz, CDCl3) delta ppm: 1.36 (6H, s), 2.89 (2H, s), 7.03 (1H, dd, J=1.4, 6.9Hz) 7.18-7.24 (2H, m), 7.60 (1H, t, J=8.2Hz), 7.77 (1H, ddd, J=1.3, 6.9, 8.2Hz), 7.88 (1H, d, J=8.2Hz), 8.16 (1H, d, J=8.2Hz), 8.36 (1H, d, J=2.1Hz), 9.09 (1H, d, J=2.1Hz). MS m/z: 304(M+), 303, 289, 248, 156. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In water; at 120℃; for 24h;Sealed vessel; | Step 1 : Potassium quinoline-3-carboxylateIn a sealable tube, quinoline-3-carbonitrile (308 mg, 2.0 mmol) was suspended in I M potassium hydroxide (3 mL), and the reaction vessel was sealed and heated at 120 0C for 24 h. The mixture was cooled to ambient temperature, and concentrated. The crude material was used directly in the next step. MS m/z: 174 (M+l of acid). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13% | With sodium tetrahydroborate; nickel dichloride; In methanol; at 0 - 20℃; for 1.33333h; | PREPARATION 16; Preparation of quinolin-3-ylmethanaminium chloride; A. To a stirred solution of <strong>[34846-64-5]<strong>[34846-64-5]3-quinolinecarbonitril</strong>e</strong> ( 1.00 g. 6.49 mmol) in methanol (50 mL) at 0 0C was added dkappa<?r/-butyl dicarbonate (2.83 g. 12.97 mmol). followed by the addition of nickel chloride hexahydrate (0.15 g. 0.65 mmol). Sodium borohydride was then added in small portions over 20 minutes. The resulting reaction <n="105"/>mixture was stirred at ambient temperature for 1 h. Diethylenetriamine (0.70 mL) was added, and the mixture was stirred for 30 minutes. The solvent was removed in vacuo. The residue was taken up in saturated aqueous sodium bicarbonate solution ( 100 mL) and extracted with dichloromethane (2 chi 100 mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with 60% ethyl acetate in hexanes, and then triturated with dichloromethane. The insoluble material was filtered off, and the filtrate was concentrated in vacuo to afford fetau/-butyl quinolin-3-ylcarbamate as a colorless solid in 13% yield (0.21 g): 1H NMR (300 MHz, CDCl3) delta 8.86 (d, J= 1.8 Hz, I H), 8.10 (d, J =8.3 Hz, 1 H), 8.05 (s, 1 H), 7.80 (d, J = 8.3 Hz, 1 H), 7.74-7.66 (m, 1 H), 7.59-7.51 (m, 1 H),5.04 (br s, I H), 4.51 (d, J= 5.8 Hz, 2H), 1.47 (s, 9H); MS (ES+) nv'z 259.2 (M + 1 ). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With potassium tert-butylate; In para-xylene; at 120℃; for 4h;Inert atmosphere; | General procedure: To a solution of adiponitrile (219 muL, 1.95 mmol) and the appropriate mononitrile (1.30 mmol) in p-xylene (1 mL) in a carousel tube was added t-BuOK (29.2 mg, 0.26 mmol) in one portion. The reaction vessel was heated in a carousel to 120 C for 4 h. After cooling to room temperature, CH2Cl2 (ca. 30 mL) was used to transfer the mixture onto a silica cartridge for purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
<strong>[34846-64-5]Quinoline-3-carbonitrile</strong> (2-Im-10, 10 g) was suspended in 65 mL of MeOH, then NaOCH3 (0.1 eq) was added and the reaction was stirred at 25 C for 15 h. 2,2-Dimethoxyethanamine (1 eq) was added, followed by acetic acid (2 eq) and the mixture was heated at 50 C for lh. The reaction was cooled to rt and 30 mL of 6N HC1 was added to give a pH=l and this mixture was heated at reflux for 5 h. The 8576.98-304 reaction was diluted with 200 mL of water and extracted with EtOAc (2 x 200 rnL). The aqueous phase was made basic (pH=10) with solid sodium carbonate and the desired compound precipitated out and was isolated by filtration and washed with water to give Imidazole 10. LCMS (0.01% Ammonia): 196.2 m/z (M+H)+; ^- MR (DMSO-d6, 500MHz): delta: 12.92 (bs, 1H), 9.51 (d, 1H, J=2.0Hz), 8.78 (d, 1H, J=2.0Hz), 8.03 (dd, 2H, J=8.5Hz), 7.77 (t, 1H, J=8.0Hz), 7.65 (t, 1H, J=8.0Hz), 7.28 (bs, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In pyridine; at 250℃; for 0.5h;microwave irradiation; | A suspension of 3-bromoquinoline (l-Im-10, 1.5g) and CuCN (3 eq) in 10 mL of pyridine in a 25 mL microwave tube was heated at 250 C for 30min in a microwave. This was repeated 10 times and the reactions were combined and diluted with 200 mL of EtOAc. The solids were removed by filtration and the EtOAc solution concentrated. The residue was taken up in a solution prepared from 80 mL of 30% aqueous H3 and 800 mL of water. This was extracted with EtOAc (4 x 800mL) then the combined extracts were dried with anhydrous Na2S04, concentrated and purified by silica gel chromatography (PE: EtOAc = 3: 1) to give quinoline-3- carbonitrile (2-Im-10). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In dichloromethane;Inert atmosphere; Schlenk technique; Reflux; | General procedure: To a stirred suspension of 0.5mmol of [FeCp(dppe)I] in dichloromethane (25mL) was added 0.6mmol of the adequate ligand (L1=2-quinolinecarbonitrile; L2=<strong>[34846-64-5]<strong>[34846-64-5]3-quinolinecarbonitril</strong>e</strong>; L3=2-pyrazinecarbonitrile; L4=2,3-pyrazinedicarbonitrile) followed by addition of 0.6mmol of TlPF6 (for complexes 1, 2, 3 and 4) or AgCF3SO3 (for complex 3). After refluxing for a period of 5-6h the color changed from gray to orange reddish. The reaction mixture was cooled down to room temperature and the solution was filtered to eliminate the TlCl or the AgCl precipitate. The solvent was then removed under vacuum and the residue was washed with n-hexane (2×10mL). Dark red crystals were obtained after recrystalization from dichloromethane/n-hexane solutions. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In dichloromethane;Inert atmosphere; Schlenk technique; Reflux; | General procedure: To a stirred suspension of 0.5mmol of [FeCp(dppe)I] in dichloromethane (25mL) was added 0.6mmol of the adequate ligand (L1=2-quinolinecarbonitrile; L2=<strong>[34846-64-5]<strong>[34846-64-5]3-quinolinecarbonitril</strong>e</strong>; L3=2-pyrazinecarbonitrile; L4=2,3-pyrazinedicarbonitrile) followed by addition of 0.6mmol of TlPF6 (for complexes 1, 2, 3 and 4) or AgCF3SO3 (for complex 3). After refluxing for a period of 5-6h the color changed from gray to orange reddish. The reaction mixture was cooled down to room temperature and the solution was filtered to eliminate the TlCl or the AgCl precipitate. The solvent was then removed under vacuum and the residue was washed with n-hexane (2×10mL). Dark red crystals were obtained after recrystalization from dichloromethane/n-hexane solutions. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; potassium carbonate; cesium pivalate; In acetonitrile; at 110℃; for 18h;Inert atmosphere; Schlenk technique; | General procedure: N-sulfonyl 2-aminobenzaldehyde (0.2 mmol), acrylate ester(0.8 mmol), [Cp*RhCl2]2 (2.5 mol%), Ag2CO3 (0.4 mmol), andK2CO3 (0.6 mmol) were charged into a pressure tube, andCH3CN (2 mL) was added under Ar. The reaction mixture wasstirred at 110 C for 18 h. After cooling to room temperature,the solvent was removed under reduced pressure and the residuewas purified by silica gel chromatography using EA/PE toafford the cyclization product. |
Tags: 34846-64-5 synthesis path| 34846-64-5 SDS| 34846-64-5 COA| 34846-64-5 purity| 34846-64-5 application| 34846-64-5 NMR| 34846-64-5 COA| 34846-64-5 structure
[ 42885-14-3 ]
5-Methylpyridine-3-carbonitrile
Similarity: 0.78
[ 95104-21-5 ]
2-Chloroquinoline-3-carbonitrile
Similarity: 0.77
[ 95104-21-5 ]
2-Chloroquinoline-3-carbonitrile
Similarity: 0.77
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H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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