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CAS No. : | 35736-52-8 | MDL No. : | MFCD08282833 |
Formula : | C7H7Br2NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RBFJSDKTASSGSH-UHFFFAOYSA-N |
M.W : | 280.95 | Pubchem ID : | 13399540 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 52.74 |
TPSA : | 35.25 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.17 cm/s |
Log Po/w (iLOGP) : | 2.22 |
Log Po/w (XLOGP3) : | 2.59 |
Log Po/w (WLOGP) : | 2.81 |
Log Po/w (MLOGP) : | 2.64 |
Log Po/w (SILICOS-IT) : | 2.46 |
Consensus Log Po/w : | 2.54 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.55 |
Solubility : | 0.079 mg/ml ; 0.000281 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.98 |
Solubility : | 0.295 mg/ml ; 0.00105 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.87 |
Solubility : | 0.0382 mg/ml ; 0.000136 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.66 |
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 |
---|---|---|
23% | With N-Bromosuccinimide In chloroform at 5 - 20℃; | m-Anisidine (5.00 g, 40.6 mmol) was dissolved in chloroform (40 mL) and the solution was chilled to 5 °C. N-Bromosuccinimide (7.23 g, 40.6 mmol) was added portionwise to the chilled solution over a 1 h period and the mixture was then stirred for another 4 h in an ice bath at 5-10 °C. The reaction mixture was allowed to warm at room temperature and stirring was continued overnight. The mixture was washed with sodium hydroxide (2 M, 50 mL), followed by water (60 mL) and dried over anhydrous sodium sulfate. The solvent was evaporated to afford a dark brown viscous liquid. The crude material was chromatographed (silica gel, dichloromethane/hexane 2:1) to afford a mixture of 2-bromo-5-methoxyaniline and 2,4-dibromo-5-methoxyaniline as the first major band eluted. Subsequently, another major band was eluted to afford 4-bromo-3-methoxyaniline (860 mg, 10percent) as peach coloured crystals: mp 97-98 °C (lit.65 93-94 °C); 1H NMR (400 MHz, CDCl3) δ 3.70 (br s, 2H, NH2), 3.80 (s, 3H, OCH3), 6.16 (dd, J 2.5, 8.4 Hz, 1H, ArH), 6.23 (d, J 2.5 Hz, 1H, ArH), 7.23 (d, J 8.4 Hz, 1H, ArH). The data are in agreement with those reported in the literature.65 The first major band was evaporated to dryness and rechromatographed (silica gel, ethyl acetate/hexane 1:2) to afford 2-bromo-5-methoxyaniline (830 mg, 10percent) as an orange liquid. 1H NMR (400 MHz, CDCl3) δ 3.72 (s, 3H, OCH3), 4.07 (br s, 2H, NH2), 6.21 (dd J 2.9, 8.8 Hz, 1H, ArH), 6.30 (d, J 2.9 Hz, 1H, ArH), 7.25 (d, J 8.8 Hz, 1H, ArH). The data are in agreement with those reported in the literature.65 This was followed by the elution of a second band that afforded 2,4-dibromo-5-methoxyaniline (2.66 g, 23percent) as a brown liquid. Rf (80percent EtOAc/CH2Cl2) 0.87; IR (neat) νmax 3420, 3295, 3176, 2965, 2934, 1620, 1582, 1503, 1278, 1207, 1018, 805 cm-1; 1H NMR (400 MHz, CDCl3) δ 3.80 (s, 3H, OCH3), 4.10 (br s, 2H, NH2), 6.31 (s, 1H, ArH), 7.49 (s, 1H, ArH); 13C NMR (100 MHz, CDCl3) δ 56.1, 99.3, 99.3, 99.7, 135.1, 144.3, 155.8; Anal. Calcd for C7H7Br2NO: C, 29.93; H, 2.51; N, 4.99. Found: C 30.29; H 2.24; N 4.95percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With N-Bromosuccinimide In chloroform at 5 - 20℃; | m-Anisidine (5.00 g, 40.6 mmol) was dissolved in chloroform (40 mL) and the solution was chilled to 5 °C. N-Bromosuccinimide (7.23 g, 40.6 mmol) was added portionwise to the chilled solution over a 1 h period and the mixture was then stirred for another 4 h in an ice bath at 5-10 °C. The reaction mixture was allowed to warm at room temperature and stirring was continued overnight. The mixture was washed with sodium hydroxide (2 M, 50 mL), followed by water (60 mL) and dried over anhydrous sodium sulfate. The solvent was evaporated to afford a dark brown viscous liquid. The crude material was chromatographed (silica gel, dichloromethane/hexane 2:1) to afford a mixture of 2-bromo-5-methoxyaniline and 2,4-dibromo-5-methoxyaniline as the first major band eluted. Subsequently, another major band was eluted to afford 4-bromo-3-methoxyaniline (860 mg, 10percent) as peach coloured crystals: mp 97-98 °C (lit.65 93-94 °C); 1H NMR (400 MHz, CDCl3) δ 3.70 (br s, 2H, NH2), 3.80 (s, 3H, OCH3), 6.16 (dd, J 2.5, 8.4 Hz, 1H, ArH), 6.23 (d, J 2.5 Hz, 1H, ArH), 7.23 (d, J 8.4 Hz, 1H, ArH). The data are in agreement with those reported in the literature.65 The first major band was evaporated to dryness and rechromatographed (silica gel, ethyl acetate/hexane 1:2) to afford 2-bromo-5-methoxyaniline (830 mg, 10percent) as an orange liquid. 1H NMR (400 MHz, CDCl3) δ 3.72 (s, 3H, OCH3), 4.07 (br s, 2H, NH2), 6.21 (dd J 2.9, 8.8 Hz, 1H, ArH), 6.30 (d, J 2.9 Hz, 1H, ArH), 7.25 (d, J 8.8 Hz, 1H, ArH). The data are in agreement with those reported in the literature.65 This was followed by the elution of a second band that afforded 2,4-dibromo-5-methoxyaniline (2.66 g, 23percent) as a brown liquid. Rf (80percent EtOAc/CH2Cl2) 0.87; IR (neat) νmax 3420, 3295, 3176, 2965, 2934, 1620, 1582, 1503, 1278, 1207, 1018, 805 cm-1; 1H NMR (400 MHz, CDCl3) δ 3.80 (s, 3H, OCH3), 4.10 (br s, 2H, NH2), 6.31 (s, 1H, ArH), 7.49 (s, 1H, ArH); 13C NMR (100 MHz, CDCl3) δ 56.1, 99.3, 99.3, 99.7, 135.1, 144.3, 155.8; Anal. Calcd for C7H7Br2NO: C, 29.93; H, 2.51; N, 4.99. Found: C 30.29; H 2.24; N 4.95percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With N-Bromosuccinimide In chloroform at 5 - 20℃; | m-Anisidine (5.00 g, 40.6 mmol) was dissolved in chloroform (40 mL) and the solution was chilled to 5 °C. N-Bromosuccinimide (7.23 g, 40.6 mmol) was added portionwise to the chilled solution over a 1 h period and the mixture was then stirred for another 4 h in an ice bath at 5-10 °C. The reaction mixture was allowed to warm at room temperature and stirring was continued overnight. The mixture was washed with sodium hydroxide (2 M, 50 mL), followed by water (60 mL) and dried over anhydrous sodium sulfate. The solvent was evaporated to afford a dark brown viscous liquid. The crude material was chromatographed (silica gel, dichloromethane/hexane 2:1) to afford a mixture of 2-bromo-5-methoxyaniline and 2,4-dibromo-5-methoxyaniline as the first major band eluted. Subsequently, another major band was eluted to afford 4-bromo-3-methoxyaniline (860 mg, 10percent) as peach coloured crystals: mp 97-98 °C (lit.65 93-94 °C); 1H NMR (400 MHz, CDCl3) δ 3.70 (br s, 2H, NH2), 3.80 (s, 3H, OCH3), 6.16 (dd, J 2.5, 8.4 Hz, 1H, ArH), 6.23 (d, J 2.5 Hz, 1H, ArH), 7.23 (d, J 8.4 Hz, 1H, ArH). The data are in agreement with those reported in the literature.65 The first major band was evaporated to dryness and rechromatographed (silica gel, ethyl acetate/hexane 1:2) to afford 2-bromo-5-methoxyaniline (830 mg, 10percent) as an orange liquid. 1H NMR (400 MHz, CDCl3) δ 3.72 (s, 3H, OCH3), 4.07 (br s, 2H, NH2), 6.21 (dd J 2.9, 8.8 Hz, 1H, ArH), 6.30 (d, J 2.9 Hz, 1H, ArH), 7.25 (d, J 8.8 Hz, 1H, ArH). The data are in agreement with those reported in the literature.65 This was followed by the elution of a second band that afforded 2,4-dibromo-5-methoxyaniline (2.66 g, 23percent) as a brown liquid. Rf (80percent EtOAc/CH2Cl2) 0.87; IR (neat) νmax 3420, 3295, 3176, 2965, 2934, 1620, 1582, 1503, 1278, 1207, 1018, 805 cm-1; 1H NMR (400 MHz, CDCl3) δ 3.80 (s, 3H, OCH3), 4.10 (br s, 2H, NH2), 6.31 (s, 1H, ArH), 7.49 (s, 1H, ArH); 13C NMR (100 MHz, CDCl3) δ 56.1, 99.3, 99.3, 99.7, 135.1, 144.3, 155.8; Anal. Calcd for C7H7Br2NO: C, 29.93; H, 2.51; N, 4.99. Found: C 30.29; H 2.24; N 4.95percent. |