Structure of 3-Bromo-2-methylaniline
CAS No.: 55289-36-6
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 55289-36-6 |
Formula : | C7H8BrN |
M.W : | 186.05 |
SMILES Code : | C1=CC=C(C(=C1Br)C)N |
MDL No. : | MFCD00051579 |
InChI Key : | IILVSKMKMOJHMA-UHFFFAOYSA-N |
Pubchem ID : | 123538 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 43.51 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.02 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.82 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.3 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.35 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.57 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.26 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.26 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.94 |
Solubility | 0.216 mg/ml ; 0.00116 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.48 |
Solubility | 0.61 mg/ml ; 0.00328 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.28 |
Solubility | 0.0981 mg/ml ; 0.000527 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.8 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
2.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.16 |
* 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 |
---|---|---|
45.2% | With acetic acid; at 100℃; for 2h; | 4.1.38 2-(3-Bromo-2-methylphenyl)-5-(tert-butyl)isoindoline-1,3-dione (7l) A mixture of <strong>[32703-79-0]5-(tert-butyl)isobenzofuran-1,3-dione</strong> (93 mg, 0.5 mmol), 3-bromo-2-methylaniline (100 mg, 0.5 mmol) in AcOH (2 mL) was stirred at 100 C for 2 h. The reaction mixture was cooled down to room temperature and diluted with water (10 mL), and then the NaHCO3 solution was added. The product was extracted three times with EtOAc (30 mL) and the combined organic layer was dried over Na2SO4. The solvent was removed in vacuo and the residue product was purified on a silica gel column using petroleum ether/EtOAc (4:1, v/v) as eluent to afford 7l (83 mg, 45.2%) as a gray solid. MS (ESI) m/z 372.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6): delta 7.97-7.95 (m, 1H), 8.42 (s, 1H), 7.93-7.91 (d, J = 8.60 Hz, 1H), 7.77-7.75 (d, J = 8.00 Hz, 1H), 7.44-7.43 (d, J = 7.72 Hz, 1H), 7.33-7.29 (t, J = 15.90 Hz, 1H), 2.17 (s, 3H), 1.38 (s, 9H). |
With acetic acid; at 100℃; for 1h; | To a solution of <strong>[32703-79-0]4-tert-butylphthalic anhydride</strong> (4.39 g, 21.5 mmol) in acetic acid (40 mL), 3-bromo-2-methylaniline(2.65 mL, 21.5 mmol) was added and stirred at 100 C for 1 h. The reaction mixture was concentrated under reducedpressure, and diluted with ethyl acetate (300 mL), washed with water (100 mL), saturated sodium hydrogen carbonatesolution (100 mL) and brine (100 mL), dried over sodium sulfate, filtered and concentrated. The crude material was suspended in hexane, then the precipitate was collected by filtration, washed with hexane then dried to afford 2-(3-bromo-2-methylphenyl)-5-(tert-butyl)isoindoline-1,3-di one (7.0 g). 1H NMR (400 MHz, CDCl3) delta 8.00 (dd, J = 1.7, 0.7 Hz, 1H), 7.93 - 7.77 (m, 2H), 7.67 (dd, J = 7.6, 1.8 Hz, 1H),7.24 - 7.12 (m, 2H), 2.27 (s, 3H), 1.42 (s, 9H). |
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