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CAS No. : | 72054-56-9 | MDL No. : | MFCD12025077 |
Formula : | C9H8BrN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NNNRGWOWXNCGCV-UHFFFAOYSA-N |
M.W : | 210.07 | Pubchem ID : | 12886548 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 48.8 |
TPSA : | 23.79 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) : | -5.6 cm/s |
Log Po/w (iLOGP) : | 2.15 |
Log Po/w (XLOGP3) : | 2.79 |
Log Po/w (WLOGP) : | 2.5 |
Log Po/w (MLOGP) : | 2.55 |
Log Po/w (SILICOS-IT) : | 3.14 |
Consensus Log Po/w : | 2.63 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.17 |
Solubility : | 0.141 mg/ml ; 0.000673 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.95 |
Solubility : | 0.238 mg/ml ; 0.00113 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.15 |
Solubility : | 0.0148 mg/ml ; 0.0000706 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.9 |
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 |
---|---|---|
91% | With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 5 h; | To a stirred solution of 4-(2-hydroxyethyl)benzonitrile (1.0g ,6.8mmol,1eq.) in DCM (20 mL) was added CBr4 (4.5016g, 13.6mmol, 2.0 eq) and TPP (3.835g, 13.6mmol, 2.0 eq). The resulting solution was stirred at RT for 5h. Reaction was monitored TLC. Reaction was diluted with water and extracted with EtOAc. Organic layer was dried over sodium sulfate, filtered and the filtrated concentrated. The crude compound was isolated by column chromatography to get pure 4-(2-bromoethyl)benzonitrile (1.3 g, 91percent). LC-MS (method 23): Rt = 2.01 min; m/z = 210.05 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | for 2 h; Reflux | Example 8A 4-(2-Bromoethyl)benzonitrile A solution of 29.3 g (0.14 mol) of 4-(2-bromoethyl)benzaldehyde from Example 7A in 112.4 ml of formic acid is mixed with 12.42 g (0.18 mol) of hydroxylamine hydrochloride and heated to reflux for 2 hours. After slow cooling to room temperature, 670 ml of water are added, and the reaction mixture is slowly neutralized with 6 N sodium hydroxide solution while cooling. The mixture is then extracted three times with methyl tert-butyl ether. The combined organic phases are dried over magnesium sulfate and concentrated to dryness. The resulting residue is purified by flash chromatography on silica gel (mobile phase: dichloromethane). 21.3 g (0.10 mol, 74percent yield) of a yellowish solid are obtained. 1H-NMR (400 MHz, DMSO-d6, δ/ppm): 7.80 (2H, d), 7.51 (2H, d), 3.77 (2H, t), 3.22 (2H, t). MS (DCI, NH3): 227 (M+NH4+). |
74% | for 2 h; Reflux | Example 4A; 4-(2-Bromoethyl)benzonitrile 12.42 g (0.18 mol) of hydroxylamine hydrochloride are added to a solution of 29.3 g (0.14 mol) of 4-(2-bromoethyl)benzaldehyde in 112.4 ml of formic acid, and the mixture is heated under reflux for 2 hours. After slowly cooling to room temperature, 670 ml of water are added and the reaction mixture is slowly neutralized with 6 N sodium hydroxide solution while cooling. The mixture is then extracted three times with methyl tert-butyl ether. The combined organic phases are dried over magnesium sulphate and evaporated to dryness. The resulting residue is purified by flash chromatography on silica gel (mobile phase: dichloromethane). 21.3 g (0.10 mol, 74percent yield) of a yellowish solid are obtained.1H-NMR (400 MHz, DMSO-d6, δ/ppm): 7.80 (2H, d), 7.51 (2H, d), 3.77 (2H, t), 3.22 (2H, t).MS (DCI, NH3): m/z=227 (M+NH4+). |
74% | for 2 h; Reflux | A solution of 29.3 g (0.14 mol) of 4-(2-bromoethyl)benzaldehyde in 112.4 ml of formic acid is mixed with 12.42 g (0.18 mol) of hydroxylamine hydrochloride and heated under reflux for 2 hours. After slow cooling to room temperature, 670 ml of water are added, and the reaction mixture is slowly neutralized with 6 N sodium hydroxide solution while cooling. The mixture is then extracted three times with methyl tert-butyl ether. The combined organic phases are dried over magnesium sulfate and concentrated. The resulting residue is purified by flash chromatography on silica gel (mobile phase: dichloromethane). 21.3 g (0.10 mol, 74percent of theory) of a yellowish solid are obtained.1H-NMR (400 MHz, DMSO-d6, δ/ppm): 7.80 (2H, d), 7.51 (2H, d), 3.77 (2H, t), 3.22 (2H, t).MS (DCI, NH3): 227 (M+NH4+). |
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