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CAS No. : | 906673-54-9 | MDL No. : | MFCD23131224 |
Formula : | C14H8BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IEHZPKWXBVTRRG-UHFFFAOYSA-N |
M.W : | 302.12 | Pubchem ID : | 118988938 |
Synonyms : |
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 70.76 |
TPSA : | 50.09 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) : | -5.37 cm/s |
Log Po/w (iLOGP) : | 2.55 |
Log Po/w (XLOGP3) : | 3.91 |
Log Po/w (WLOGP) : | 3.93 |
Log Po/w (MLOGP) : | 2.56 |
Log Po/w (SILICOS-IT) : | 3.87 |
Consensus Log Po/w : | 3.36 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.47 |
Solubility : | 0.0102 mg/ml ; 0.0000337 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.66 |
Solubility : | 0.0066 mg/ml ; 0.0000219 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.53 |
Solubility : | 0.000892 mg/ml ; 0.00000295 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.11 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
99% | at 10 - 30℃; | lOOg of 4-(4-bromo-3-fonnylphenoxy) benzonitrile (VI) was dissolved in 500mL of methanol at 25-30 °C and then cooled to 10-15 °C. 6.2 g of sodium borohydride was added to the reaction mass at 10-15 °C for 60-90 mm. The temperature of the reaction mass was raised to 15-20 °C. After completion of the reaction, 1000 mL of water was added to the reaction mass, stirred forlhr at 25-30 °C. The solid obtained was filtered under vacuum, washed with water and dried under vacuum below 55 °C to obtain 4-(4-bromo-3-(hydroxymethyl) phenoxy) benzonitrile (V).Yield percent: 99.0; Purity percent: 99.02 |
92% | at 25℃; for 4 h; | Will be 30.2g (0.1mol) 4-[(4-bromo-3-formyl)phenoxy)]benzonitrile (compound of formula I), 400 ml of methanol was added to the reaction kettle. 1.89 g (0.1 mol) of sodium borohydride was added in portions. After the addition, stirring was continued for 4 h at 25 ° C until the reaction of the starting material was complete. Recovering methanol, Add 1000ml of water to beat, filter, Drying to obtain a solid 27.8, yield 92percent; |
80% | With sodium tetrahydroborate; water; sodium hydroxide In methanol at 0℃; for 1 h; Inert atmosphere | In a round bottom flask, under nitrogen atmosphere, a mixture of 4-(4-bromo-3- formylphenoxy)benzonitrile (compound A) (28.1 g, 93 mmol) and methanol (1 12 ml) was prepared and cooled to 0 °C. To the resulting suspension, a solution of sodium borohydride (1 .79 g, 46.5 mmol), water (5.9 ml) and 1 M NaOH (0.2 ml) was added dropwise for 15 minutes. The reaction mixture was stirred for 1 hour at 0 °C and 3M HCI was added until pH 4.5. Afterwards, water (1 12 ml) was added and the suspension was stirred for 1 hour at room temperature. The resulting solid was filtered and purified by recrystallization from a mixture of methanol to give 4-(4-bromo-3-(hydroxymethyl)phenoxy)benzonitrile (compound B). Yield: 80percent Purity by HPLC: >99.9percent 1H-NMR (200 MHz, DMSO-d6, δ ppm): 7.81-7.86 (2H, d, J=8); 7.60-7.64 (1 H, d, J=8 Hz); 7.21-7.22 (1 H, d, J=3 Hz), 7.10-7.14 (2H, d, J=8), 6.96-7.02 (1 H, dd, J=8, J=3), 5.51-5.56 (1 H, t, J=5), 4.46-4.48 (2H, d, J=5) 13C-NMR (50 MHz, DMSO-d6, δ ppm): 161.04; 154.74; 144.08; 135.07; 134.08; 120.53; 1 19.73; 1 19.02; 1 18.82; 1 16.30; 106.02; 62.83 DSC: Endothermic peak at 94.2 °C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With potassium carbonate In N,N-dimethyl-formamide; toluene at 115℃; for 8 h; Inert atmosphere | In a round bottom flask, under nitrogen atmosphere, 2-bromo-5-hydroxybenzaldehyde (100 g, 497 mmol) and 4-fluorobenzonitrile (301 .2 g, 2487 mmol) were dissolved in DMF (250 ml) and toluene (500 ml). To the resulting dark solution, potassium carbonate (206.2 g, 1492 mmol) was added and the resulting mixture was stirred for 8 hours at 1 15 °C. After the reaction was completed by TLC, the heterogeneous mixture was filtered. The solvents and 4-fluoro-benzonitrile were distilled under reduced pressure from the obtained filtrate. Ethyl acetate (800 ml), water (500 ml) and brine (40 ml) were added and the formed phases were separated at 65-70 °C. The aqueous phase was extracted with ethyl acetate (150 ml) at 65-70 °C and the combined organic phase was washed with a mixture of water (225 ml) and brine (180 ml) at 65-70 °C. The obtained organic phase was evaporated under reduced pressure to give a brown solid. The solid was purified twice by recrystallization in a hot mixture of ethyl acetate and toluene to give 4-(4-bromo-3- formylphenoxy)benzonitrile (compound A) (107.5 g). Yield: 71 percent Purity by HPLC: >99percent 1H-NMR (200 MHz, CDCI3, δ ppm): 10.32 (1 H, s); 7.62-7.72 (3H, m); 7.57-7.59 (1 H, dd; J= 3, J= 1 ); 7.18- 7.23 (1 H, dd, J=8 Hz, J=3 Hz), 7.01 -7.08 (2H, m) 13C-NMR (50 MHz, CDCI3, δ ppm): 190.69; 160.08; 155.13; 135.59; 134.89; 134.39; 126.86; 121.81 ; 120.28; 1 18.68; 1 18.33; 107.32 DSC: Endothermic peak at 1 1 1.9 °C. |
50 g | With potassium carbonate In N,N-dimethyl-formamide at 75 - 85℃; for 20 h; | A mixture of 2-bromo-5-hydroxybenzaldehyde (50g), 4-fluorobenzonitrile (75.3 lg) and potassium carbonate (103g) in dimethylformamide (500mL) was stirred at about 75°C to about 85°C for about 20h. The reaction mixture was filtered and the filtrate was quenched with water at about room temperature, stirred for about 2h, filtered and dried. The crude product was purified by ethyl acetate. Yield: 50g HPLC purity: >99percent |
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