Structure of 4-Chloro-3-methylaniline
CAS No.: 7149-75-9
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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. : | 7149-75-9 |
Formula : | C7H8ClN |
M.W : | 141.60 |
SMILES Code : | NC1=CC=C(Cl)C(C)=C1 |
MDL No. : | MFCD00066332 |
InChI Key : | HIHCTGNZNHSZPP-UHFFFAOYSA-N |
Pubchem ID : | 23536 |
GHS Pictogram: |
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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 | 40.82 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.02 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.7 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.66 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.24 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.41 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.23 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.25 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.89 |
Solubility | 0.184 mg/ml ; 0.0013 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.86 |
Solubility | 0.196 mg/ml ; 0.00139 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.02 |
Solubility | 0.137 mg/ml ; 0.000966 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 |
-5.28 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) |
1.0 |
* 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 |
---|---|---|
With tin(II) chloride dihdyrate; In ethyl acetate; for 2.5h;Reflux; Inert atmosphere; | General procedure: A mixture of 10, (7.8 mmol) and SnCl2.2H2O (39 mmol) in EtOAc (75 mL) was stirred at reflux under nitrogen for 2.5 h. Upon cooling, saturated NaHCO3 (150 mL) was added. The organic layer was separated and the aqueous layer washed with EtOAc (2 × 100 mL). The combined organic layers were dried (Na2SO4) and concentrated to dryness to give 11 as a white solid (86percent). | |
99%Chromat. | With hydrazine hydrate; In ethanol; at 80℃; for 1h;Inert atmosphere; | General procedure: Hydrazine hydrate was chosen as the hydrogen donor for the low emission of pollutants. In a typical procedure, hydrazine hydrate (4 equiv) was added into the reactor which containing fresh prepared catalyst as described above. Then the reactor was put into a preheated oil bath with a stirring speed of 500 rpm, and the substrate (1 mmol)dissolved in 1 mL ethanol was added drop-wisely under argon. The reactions were monitored by TLC. After the reaction, the reaction mixture was vacuum filtered through a pad of silica on a glass-fritted funnel and an additional 15 mL of ethyl acetate (5 mL portions) was used to rinse the product from the silica, the filtrate was concentrated in vacuum and analyzed by GC. Products were purified by column chromatography and identified by 1H NMR and 13C NMR. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With copper(II) choride dihydrate; lithium chloride hydrate; In ethanol; for 4h;Reflux; | General procedure: A round-bottomed flask (25 mL) was charged with substrate (2 mmol), CuCl2·2H2O (6 mmol), LiCl·H2O (2 mmol) and EtOH (4 mL). The resulting reaction mixture was stirred at reflux. After the completion of the reaction monitored by TLC, EtOH was removed under reduced pressure. Then ammonium hydroxide (4 mL, 25percent) and water (10 mL) were added and the aqueous phase was extracted with ethyl acetate (10 mL×3). The combined organic phase was washed with brine (8 mL×3) and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure. The crude mixture was purified by chromatography on silica gel to obtain the desired products. |