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CAS No. : | 935-44-4 | MDL No. : | MFCD00001270 |
Formula : | C10H9N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZHFURHRJUWYDKG-UHFFFAOYSA-N |
M.W : | 143.19 | Pubchem ID : | 70288 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.3 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 43.35 |
TPSA : | 23.79 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.81 cm/s |
Log Po/w (iLOGP) : | 2.0 |
Log Po/w (XLOGP3) : | 1.92 |
Log Po/w (WLOGP) : | 2.18 |
Log Po/w (MLOGP) : | 2.01 |
Log Po/w (SILICOS-IT) : | 2.88 |
Consensus Log Po/w : | 2.2 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.27 |
Solubility : | 0.76 mg/ml ; 0.00531 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.04 |
Solubility : | 1.3 mg/ml ; 0.00905 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.28 |
Solubility : | 0.0757 mg/ml ; 0.000528 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312-P304+P340+P312-P363-P501 | UN#: | N/A |
Hazard Statements: | H302-H312-H332 | 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 |
---|---|---|
73% | With tetrabutylammomium bromide; potassium hydroxide In water at 50℃; for 1 h; | Step 1: Preparation of l-phenylcyclopropanecarbonitrileTo a stirred solution of phenylacetonitrile (100 g, 0.8547 mol) in aqueous solution of KOH (447g in 420 mL of water) and 2.7g of tetrabutyl ammonium bromide was added 1,2-dibromoethane (147ml, 1.709mol) drop wise by maintaining exothermicity at 50 °C.The reaction mixture was stirred at 50 °C for 1 hr, and then poured in cold water and extracted in diisopropyl ether .Crude product was purified by high vacuum distillation which afforded 90g of colourless liquid compound in 73 percent yield. |
50% | Stage #1: With potassium hexamethylsilazane In tetrahydrofuran at 0℃; for 0.5 h; Stage #2: at 0 - 20℃; |
Example 13 2-Phenyl-2-cyclopropyl ethylamine; To a cooled solution of 2-phenylacetonitrile (5.85 g, 50 mmol) in THF (200 ml) was added potassium bis (trimethylsiylyl) amide (29.92 g, 150 MMOL). The resulting mixture was stirred under N2 at 0°C for 30 min. To the resulting mixture was added dropwise a solution of 1,2-dibromoethane (10.33 g, 55 mmol) in THF (30 ml). The reaction mixture was stirred under N2 at 0°C and gradually allowed to warm to room temperature. Then it was stirred at room temperature overnight. It was concentrated in vacuo. The 1-PHENYL-1-CYCLOPROPANECARBONITRILE was obtained by distillation (3.6 g, 50percent). 1H NMR (CDC13, 300 MHz) 8 7.27-7. 38 (m, 5H), 1.69-1. 76 (m, 2H), 1.37-1. 44 (m, 2H). 1-PHENYL-1-CYCLOPROPANECARBONITRILE (1.0 g, 6.98 mmol) was added to a stirred suspension of lithium aluminum hydride (0.27 g, 6.98 mmol) in ether (25 ml). The resulting suspension was refluxed for 2 hrs, them cooled to 0°C by applying an external ice bath. The excess hydride was quenched by careful addition of H2O. The resulting mixture was filtered. The solid was washed with ether and filtered. The filtrate was dried (MgS04), and filtered. The filtrate was concentrated in vacuo to give 2-CYCLOPROPYL-2-PHENYLETHYLAMINE. HNMR (DMSO-d6,300 MHz) 8 7.28 (M, 4H), 7.17 (M, 1H), 2.70 (s, 2H), 1.45 (br s, 2H), 0.78 (dd, J = 6.2, 3.8 H, 2H), 0.67 (dd, J = 6. 2,3. 8HZ, 2H). |
41% | Stage #1: With sodium hydride In dimethyl sulfoxide at 0℃; for 0.0833333 h; Stage #2: at 20 - 35℃; for 2 h; |
Step (v): Synthesis of 1-phenylcyclopropanecarbonitrileExperimental procedure : To a solution of NaH ( 12.6 g, 525 mmoles) in DMSO (300 mL) was added phenylacetonitrile (20 g, 170.9 mmoles) in DMSO at 0 °C and the mixture was stirred for 5 min. 1,2 dibromoethane (16.29 mL 86.6 mmoles) in DMSO was added to the reaction mixture and the contents were stirred for 2 h at about 20-35 °C. The reaction mixture was treated with isopropanol (10 mL), ice cold water (150 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with brine solution (2 x 100 mL), dried over Na2S04 and concentrated under reduced pressure to give the crude product. The crude was purified by flash chromatography over silica gel (230-400 mesh). Elution with 2percent ethyl acetate in hexane, gave the desired product as a yellow liquid (10 g, 41percent).1H NMR (400 MHz, DMSO-i3/4): δ 7.42-7.29 (m, 5H), 1.80-1.69 (m, 2H), 1.55-1.44 (m, 2H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With nitrogen In <i>N</i>-methyl-acetamide; water; mineral oil | Preparation of 1-phenylcyclopropanecarbonitrile To a dry 250 ml round bottom flask equipped with magnetic stirrer, side arm addition funnel and nitrogen inlet was charged 2.7 g (0.068 moles, 2.0eq) of 60percent sodium hydride in mineral oil, and 100 mls of dry dimethylformamide. The benzyl cyanide (4.0 g, 0.034 moles, 1.0eq.) was then added dropwise and the flask was stirred at ambient temperature for 30 min. The dibromoethane (8.0 g, 0.034 moles, 1.0eq.) was then added dropwise, and the reaction was stirred at ambient temperature for 3 hours. The reaction was carefully quenched with 200 mls of water. and extracted with 3 x100 mls of ethyl ether. The ether extract was washed with 2 x 100 mls of water, 100 mls of saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated on a rotary evaporator to afford 4.9 g of a clear reddish liquid (100percent isolated yield.consistent) with the desired product, 1-phenylcyclopropanecarbonitrile, upon analysis by 300 MHz 1H NMR. NMR (300 MHz, 1H, CDCl3, TMS=0 ppm) 1.45 (m, 2H), 1.8 (m, 2H), 7.2-7.5 (m, 5H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | at 110℃; Reflux | Step (vi): Synthesis of 1-phenylcyclopropanecarboxylic acidExperimental procedure: To a solution of 1-phenylcyclopropanecarbonitrile (7 g, mmoles) was added water (15 mL), acetic acid (15 mL) and sulfuric acid (15 mL). The contents were then refluxed at 110 °C over night. The reaction mixture was extracted with ethyl acetate and the organic layer was washed with brine solution (2 x 50 mL), dried over Na2S04 and concentrated under reduced pressure to give the crude product. The crude was purified by flash column chromatography over silica gel (230-400 mesh) and elution with 5percent ethyl acetate in hexane, gave the desired product as a colorless solid (4.35 g, 50percent). |
12 g | With water; potassium hydroxide In ethanol at 100℃; for 16 h; | Potassium hydroxide solution in water (50percent, 100 mL) was added into a solution of 1- phenylcyclopropanecarbonitrile (20 g) in ethanol (100 mL) at room temperature. The reaction mixture was stirred at 100°C for 16 hours before being cooled to room temperature. The reaction mixture was concentrated to remove ethanol and the aqueous layer was washed with dichloromethane (2 x 200 mL). The aqueous layer was slowly neutralized with concentrated HCl and pH was adjusted to 3-4. The solid obtained was filtered, washed with water (3 x 50 mL) and dried under vacuum to get desired 1- phenylcyclopropanecarboxylic acid (12 g) as white solid. ^- MR (CDC13): δ 1.26-1.30 (m, 2H), 1.59-1.66 (m, 2H), 7.20-7.30 (m, 5H), 8.6 (s, 1H). MS: 163 (M + H)+. |
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