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Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
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CAS No. : | 103347-14-4 | MDL No. : | MFCD09907927 |
Formula : | C8H8BrClO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PLBDOPBECRIDKT-UHFFFAOYSA-N |
M.W : | 235.51 | Pubchem ID : | 13662859 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 50.78 |
TPSA : | 9.23 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.03 cm/s |
Log Po/w (iLOGP) : | 2.52 |
Log Po/w (XLOGP3) : | 2.41 |
Log Po/w (WLOGP) : | 3.09 |
Log Po/w (MLOGP) : | 3.17 |
Log Po/w (SILICOS-IT) : | 3.46 |
Consensus Log Po/w : | 2.93 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.09 |
Solubility : | 0.191 mg/ml ; 0.000813 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.25 |
Solubility : | 1.34 mg/ml ; 0.00568 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.41 |
Solubility : | 0.00927 mg/ml ; 0.0000394 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.67 |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P501-P260-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405 | UN#: | 1759 |
Hazard Statements: | H314 | Packing Group: | Ⅱ |
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 |
---|---|---|
100% | With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 1 h; Reflux | To a solution of 2-chloro-5-methylanisole (11) (274 g, 1.75 mol) in CC14 (2.5 L) was added benzoyl peroxide (4.23 g, 0.02 mol) and NBS (321 g, 1.80 mol). The reaction mixture was heated to reflux for 1 h with mechanical stirring. The reaction mixture was cooled, washed with IN HCl (2 L), satd NaHC03 (2 L) and brine (2 L), dried over MgS04, filtered and concentrated under reduced pressure to give the 5-(bromomethyl)-3- chloroanisole (12) as a light yellow solid (412 g, quantitative). 1H NMR (400MHz, CDC13): δ 7.30-7.34 (d, 1H), 6.95 (s, 1H), 6.91-6.93 (d, 1H), 4.45 (s, 2H), 3.92 (s, 3H). |
100% | With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 1 h; Reflux | To a solution of 2-chloro-5-methylanisole (11) (274 g, 1.75 mol) in CCl4 (2.5 L) was added benzoyl peroxide (4.23 g, 0.02 mol) and NBS (321 g, 1.80 mol). The reaction mixture was heated to reflux for 1 h with mechanical stirring. The reaction mixture was cooled, washed with IN HCl (2 L), satd NaHCO3 (2 L) and brine (2 L), dried over MgSO4, filtered and concentrated under reduced pressure to give the 5-(bromomethyl)-3- chloroanisole (12) as a light yellow solid (412 g, quantitative). 1H NMR (400MHz, CDCl3): δ 7.30-7.34 (d, IH), 6.95 (s, IH), 6.91-6.93 (d, IH), 4.45 (s, 2H), 3.92 (s, 3H). |
92% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 3 h; Heating / reflux | To a solution of 1-chloro-2-methoxy-4-methyl-benzene (50 g, 0.32 mol) in CCl4 (350 mL) was added NBS (57 g, 0.32 mol) and AIBN (10 g, 60 mmol). The mixture was heated at reflux for 3 hours. The solvent was evaporated under vacuum and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=20:1) to give 4-bromomethyl-1-chloro-2-methoxy-benzene (69 g, 92percent). 1H NMR (400 MHz, CDCl3) δ 7.33-7.31 (m, 1H), 6.95-6.91 (m, 2H), 4.46 (s, 2H), 3.92 (s, 3H). |
92% | With N-Bromosuccinimide; azobisisobutyronitrile In tetrachloromethane | 4-Bromomethyl-1-chloro-2-methoxy-benzene To a solution of 1-chloro-2-methoxy-4-methyl-benzene (50 g, 0.32 mol) in CCl4 (350 mL) was added NBS (57 g, 0.32 mol) and AIBN (10 g, 60 mmol). The mixture was heated at reflux for 3 hours. The solvent was evaporated under vacuum and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=20:1) to give 4-bromomethyl-1-chloro-2-methoxy-benzene (69 g, 92percent). 1H NMR (400 MHz, CDCl3) δ 7.33-7.31 (m, 1H), 6.95-6.91 (m, 2H), 4.46 (s, 2H), 3.92 (s, 3H). |
92% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 3 h; Reflux | 4-Bromomethyl-1-chloro-2-methoxy-benzene To a solution of 1-chloro-2-methoxy-4-methyl-benzene (50 g, 0.32 mol) in CCl4 (350 mL) was added NBS (57 g, 0.32 mol) and AIBN (10 g, 60 mmol). The mixture was heated at reflux for 3 hours. The solvent was evaporated under vacuum and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=20:1) to give 4-bromomethyl-1-chloro-2-methoxy-benzene (69 g, 92percent). 1H NMR (400 MHz, CDCl3) δ 7.33-7.31 (m, 1H), 6.95-6.91 (m, 2H), 4.46 (s, 2H), 3.92 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | at 60℃; | To a solution of 4-bromomethyl-1-chloro-2-methoxy-benzene (68.5 g, 0.290 mol) in C2H5OH (90percent, 500 mL) was added NaCN (28.5 g, 0.580 mol). The mixture was stirred at 60° C. overnight. Ethanol was evaporated and the residue was dissolved in H2O. The mixture was extracted with ethyl acetate (300 mL.x.3). The combined organic layers were washed with brine, dried over Na2SO4 and purified by column chromatography on silica gel (petroleum ether/ethyl acetate 30:1) to give 2-(4-chloro-3-methoxyphenyl)acetonitrile (25 g, 48percent). 1H NMR (400 MHz, CDCl3) δ 7.36 (d, J=8 Hz, 1H), 6.88-6.84 (m, 2H), 3.92 (s, 3H), 3.74 (s, 2H). 13C NMR (100 MHz, CDCl3) δ 155.4, 130.8, 129.7, 122.4, 120.7, 117.5, 111.5, 56.2, 23.5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | for 2 h; Reflux | To a solution of 5-(bromomethyl)-3-chloroanisole (12) (412 g, 1.75 mol) in EtOH (2 L) and H20 (0.5 L) was added NaCN (129 g, 2.63 mol) and the reaction mixture was heated to reflux for 2 h with mechanical stirring. The reaction mixture was cooled and diluted with water (3.5 L). The mixture was extracted with diethyl ether (2 L x 2) and the combined organic layers were washed with aq. 5percent HC1 (2.5 L), satd NaHC03 (2.5 L) and brine (2.5 L), dried over anhydrous MgS04, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography (Hex/EtOAc = 5: 1) to afford 2-(4-chloro-3-methoxyphenyl)acetonitrile (13) (240 g, 75percent) as yellow solid. 1H NMR (400MHz, CDC13): δ 7.35-7.36 (d, 1H), 6.86 (s, 1H), 6.84-6.86 (d, 1H), 3.92 (s, 3H), 3.74 (s, 2H). |
75% | for 2 h; Reflux | To a solution of 5-(bromomethyl)-3-chloroanisole (12) (412 g, 1.75 mol) in EtOH (2 L) and H2O (0.5 L) was added NaCN (129 g, 2.63 mol) and the reaction mixture was heated to reflux for 2 h with mechanical stirring. The reaction mixture was cooled and diluted with water (3.5 L). The mixture was extracted with diethyl ether (2 L x 2) and the combined organic layers were washed with aq. 5percent HCl (2.5 L), satd NaHCO3 (2.5 L) and brine (2.5 L), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography (Hex/EtOAc = 5:1) to afford 2-(4-chloro-3-methoxyphenyl)acetonitrile (13) (240 g, 75percent) as yellow solid. 1H NMR (400MHz, CDCl3): δ 7.35-7.36 (d, IH), 6.86 (s, IH), 6.84-6.86 (d, IH), 3.92 (s, 3H), 3.74 (s, 2H). |
48% | at 60℃; | To a solution of 4-bromomethyl-1-chloro-2-methoxy-benzene (68.5 g, 0.290 mol) in C2H5OH (90percent, 500 mL) was added NaCN (28.5 g, 0.580 mol). The mixture was stirred at 60° C. overnight. Ethanol was evaporated and the residue was dissolved in H2O. The mixture was extracted with ethyl acetate (300 mL*3). The combined organic layers were washed with brine, dried over Na2SO4 and purified by column chromatography on silica gel (petroleum ether/ethyl acetate 30:1) to give 2-(4-chloro-3-methoxyphenyl)acetonitrile (25 g, 48percent). 1H NMR (400 MHz, CDCl3) δ 7.36 (d, J=8 Hz, 1H), 6.88-6.84 (m, 2H), 3.92 (s, 3H), 3.74 (s, 2H). 13C NMR (100 MHz, CDCl3) δ 155.4, 130.8, 129.7, 122.4, 120.7, 117.5, 111.5, 56.2, 23.5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With NaCN In C2H5OH; water | 2-(4-Chloro-3-methoxyphenyl)acetonitrile To a solution of 4-bromomethyl-1-chloro-2-methoxy-benzene (68.5 g, 0.290 mol) in C2H5OH (90percent, 500 mL) was added NaCN (28.5 g, 0.580 mol). The mixture was stirred at 60° C. overnight. Ethanol was evaporated and the residue was dissolved in H2O. The mixture was extracted with ethyl acetate (300 mL*3). The combined organic layers were washed with brine, dried over Na2SO4 and purified by column chromatography on silica gel (petroleum ether/ethyl acetate 30:1) to give 2-(4-chloro-3-methoxyphenyl)acetonitrile (25 g, 48percent). 1H NMR (400 MHz, CDCl3) δ 7.36 (d, J=8 Hz, 1H), 6.88-6.84 (m, 2H), 3.92 (s, 3H), 3.74 (s, 2H). 13C NMR (100 MHz, CDCl3) δ 155.4, 130.8, 129.7, 122.4, 120.7, 117.5, 111.5, 56.2, 23.5. |
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