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CAS No. : | 6476-32-0 | MDL No. : | MFCD08271960 |
Formula : | C13H9NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BNVCOVNARIQBEO-UHFFFAOYSA-N |
M.W : | 195.22 | Pubchem ID : | 12548616 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 57.67 |
TPSA : | 33.02 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.28 cm/s |
Log Po/w (iLOGP) : | 2.37 |
Log Po/w (XLOGP3) : | 3.11 |
Log Po/w (WLOGP) : | 3.35 |
Log Po/w (MLOGP) : | 2.61 |
Log Po/w (SILICOS-IT) : | 3.04 |
Consensus Log Po/w : | 2.89 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.47 |
Solubility : | 0.0662 mg/ml ; 0.000339 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.47 |
Solubility : | 0.0659 mg/ml ; 0.000337 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.74 |
Solubility : | 0.00352 mg/ml ; 0.000018 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.93 |
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P261-P280-P305+P351+P338-P311 | UN#: | 3276 |
Hazard Statements: | H302+H312-H315-H319-H331-H335 | Packing Group: | Ⅲ |
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 |
---|---|---|
A solution of <strong>[6476-32-0]2-phenoxybenzonitrile</strong> (from step (ii) above (10.1 g, 0.0517 mol) in THF (50 ml) was added dropwise to the well-stirred suspension of LAH (4.9 g, 0.129 mol) in THF (50 ml) at 0 C. under nitrogen atmosphere and then allowed to stir at room temperature for overnight. The reaction mixture was quenched with 6(N) KOH (5 ml) 0 C. and stirred with THF (50 ml) for another 30 minutes. The reaction mixture was filtered and the residue was washed with ethyl acetate. The filtrate was concentrated to give the crude amine. Satd. HCl in diethyl ether (20 ml) was added to the solution of crude amine in diethyl ether (20 ml) and stirred for 2 h. Then the reaction mixture was filtered and residue was dried to give the title compound (10 g, 97.08 | ||
820 mg | With ammonium hydroxide; hydrogen; In methanol; at 15℃; under 775.743 Torr; for 16h; | To a solution of compound B2 (1.00 g, 5.12 mmol) in MeOH (30 mL) was added Raney-Ni (43.9 mg, 0.512 mmol) and NH3.H20 (3 mL), the reaction mixture was stirred under H2 balloon (15 psi) at l5C for 16 hours to give a black suspension. TLC showed the reaction was complete. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure to remove MeOH. The residue was diluted with DCM (20 mL), dried over anhydrous Na2S04, filtered and concentrated under reduce pressure to give compound B3 (820 mg) as a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With triethylamine; ethanaminium,N-(difluoro-lambda4-sulfanylidene)-N-ethyl-,tetrafluoroborate; In ethyl acetate; at 20℃; for 5h;Inert atmosphere; | General procedure: To a solution of the aldoxime or the amide (1.0 mmol) and Et3N (1.5mmol) in EtOAc (1 mL, 1 M) at r.t. was added XtalFluor-E8 (1.1 mmol)portionwise over ca. 2 min. The resulting solution was stirred at r.t.for 1 h. The reaction mixture was quenched with sat. aq Na2CO3 and extracted with CH2Cl2 (2 × 10 mL). The combined organic layers were washed with H2O and brine, dried (MgSO4), and concentrated under vacuum to afford the crude nitrile, which was purified by flash chromatography, if required. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 10h; | To a suspension of2-fluorobenzonitrile (10.0 g, 82.6 mmol) and phenol (7.7g,5.1 mmol) in DMF (80 mL) was added K2C03 (22.8 g, 165 mmol) at rt. The reaction was stirred at 130 oc for 10 h. The reaction mixture was diluted with water, extracted with EtAOAc (100 mLx3), washed with brine (100 mL), dried (Na2S04), and concentrated togive 15.0 g, (93%) of the title compound as a yellow oil. 1NMR (400 MHz, CDCh): 8 6.85 (1H, d, J = 8.4 Hz), 7.07-7.14 (3H, m), 7.22 (1H, t, J = 7.2 Hz), 7.40 (2H, t, J = 8.0Hz), 7.47 (1H, td, J = 2.0, 8.4 Hz), 7.65 (1H, dd, J = 1.2, 8.0 Hz). |
9.8 g | With 18-crown-6 ether; potassium carbonate; In N,N-dimethyl acetamide; at 110℃; for 16h; | To a solution of compound B1 (5.00 g, 41.3 mmol) and phenol (5.80 g, 61.9 mmol) in DMA (50 mL) was added l8-crown-6 (1.10 g, 4.13 mmol) and K2C03 (11.4 g, 82.6 mmol), the reaction mixture was stirred at H0C for 16 hours to give a brown mixture. LCMS showed the reaction was complete. To the reaction mixture was added H20 (50 mL), the reaction mixture was extracted with EtOAc (50 mL x 3), the combined organic phase was washed with H20 (40 mL x 2) and brine (100 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to give a brown oil, which was purified by Combi Flash to give compound B2 (9.80 g) as a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.8% | tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 130℃; | A solution of 1-bromo-2-phenoxybenzene from step (i) above (14.8 g, 0.0594 mol), Zn(CN)2 (6.9 g, 0.0594 mol) and Pd (PPh3)4 (6.8 g, 0.00594 mol) in dimethylformamide (100 ml) was heated at 130° C. for overnight under nitrogen atmosphere. Reaction mixture was cooled to room temperature and diluted with water (200 ml). The reaction mixture was stirred with ethyl acetate (200 ml) for 15 minutes and filtered through celite. The ethyl acetate layer was separated and washed with water, brine, dried over anh. sodium sulfate and concentrated. The crude intermediate was purified by column chromatography using 4percent ethyl acetate in pet ether to give the sub-title compound (10.1 g, 87.8percent) as colorless liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With copper(II) oxide; potassium hydroxide; In N,N-dimethyl acetamide; at 27℃; for 24h;Inert atmosphere; Sealed tube; | General procedure: A magnetic stirring bar, nanocrystalline CuO (10 mg, 3 mol %), KOH (112 mg, 2 mmol) and phenol/substituted phenol/ thiophenol (1.2 mmol) were added into an oven-dried flask (25 mL). The flask was sealed with a septum, followed by three cycles of evacuation and filling with dry nitrogen. Then aryl halide (1 mmol) and N,N-dimethyl acetamide (DMAc) (4 mL) were injected through a syringe. The flask was sealed and stirred under nitrogen until the completion of the reaction (as monitored by TLC or GC). The catalyst was recovered from the reaction mixture and washed several times with ethyl acetate. The catalyst-free reaction mixture was quenched with brine solution and the product was extracted with ethyl acetate. The combined organic extracts were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel (hexane/ethyl acetate, 80/20) to afford the product with high purity. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With C29H26FeN3Pd(1+)*Cl(1-); oxygen; caesium carbonate; In 1,4-dioxane; dimethyl sulfoxide; at 100℃; for 24h; | General procedure: A reaction vessel was charged with a mixture of phenylboronic acid (1.5mmol), Cs2CO3 (1.0mmol), catalyst Ic (1mol%) in dioxane/DMSO (1:1) (2.0mL), and stirred for about 20min under air. Then 4-nitrobenzaldehyde (0.5mmol) was then added. The mixture was heated to 100C and incubated in an oil bath at 100C for 24h under air. After the reaction was complete, the solvent was evaporated under reduced pressure. The product 3aa was obtained by purifying on preparative TLC, eluting with ethyl acetate/petroleum ether, and the yield was calculated based on the 4-nitrobenzaldehyde (the purified products were identified by NMR spectra and comparison of the melting points with the literature data). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With triethylamine; ethanaminium,N-(difluoro-lambda4-sulfanylidene)-N-ethyl-,tetrafluoroborate; In ethyl acetate; at 20℃; for 1h;Inert atmosphere; | General procedure: To a solution of the aldoxime or the amide (1.0 mmol) and Et3N (1.5mmol) in EtOAc (1 mL, 1 M) at r.t. was added XtalFluor-E8 (1.1 mmol)portionwise over ca. 2 min. The resulting solution was stirred at r.t.for 1 h. The reaction mixture was quenched with sat. aq Na2CO3 and extracted with CH2Cl2 (2 × 10 mL). The combined organic layers were washed with H2O and brine, dried (MgSO4), and concentrated under vacuum to afford the crude nitrile, which was purified by flash chromatography, if required. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | General procedure: To a solution of anisole 3A (3.0 mmol, 324.4 mg) in THF (3.0 mL) was added n-BuLi (4.5 mmol,1.55 M in hexane, 2.87 mL) at 0 C. The mixture was stirred for 2 h at 0 C under an argon atmosphere. Then, pivalonitrile (9.0 mmol, 748.2 mg) in THF (2.0 mL) was added to the mixture at 0 C and the obtained mixture was stirred for 30 min in the temperature range of 0 C to room temperature. MeOH (2.0 mL) was added to the mixture. Then, I2 (12.0 mmol, 3045.6 mg) and K2CO3 (12.0 mmol, 1658.4 mg) were added to the mixture at room temperature, and the obtained mixture was stirred for 6 h at 70 C. Sat. aq. Na2SO3 solution (20.0 mL) was added to the reaction mixture, and the product was extracted with AcOEt (10.0 mL x 3). The organic layer was dried over Na2SO4. After filtration and removal of the solvent, the residue was purified by silica-gel column chromatography (chloroform: n-hexane 1:1) to give 2-methoxybenzonitrile 2A (315.6 mg, 79%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With potassium <i>tert</i>-butylate In cyclohexane at 80℃; for 15h; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium <i>tert</i>-butylate / cyclohexane / 15 h / 80 °C / Sealed tube; Inert atmosphere 2: zinc(II) chloride / chlorobenzene / 144 h / Reflux |
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