Structure of 29866-54-4
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 29866-54-4 |
Formula : | C8H7ClO2 |
M.W : | 170.59 |
SMILES Code : | ClC1=C(C=O)C(=CC=C1)OC |
MDL No. : | MFCD08059233 |
InChI Key : | UHXUZNJCLHADGD-UHFFFAOYSA-N |
Pubchem ID : | 10964971 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 43.33 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.71 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.07 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.16 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.71 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.61 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.05 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.47 |
Solubility | 0.574 mg/ml ; 0.00336 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.25 |
Solubility | 0.956 mg/ml ; 0.0056 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.08 |
Solubility | 0.141 mg/ml ; 0.000824 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 |
-5.87 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 |
1.0 |
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) |
1.32 |
* 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 |
---|---|---|
80% | With boron tribromide; In dichloromethane; at -30 - 0℃; for 3h; | Step 5:A solution of methyl ether 15e (720 mg, 4.2 mmol) in anhydrous CH2CI2 (20 mL) is added slowly to a precooled (-30 °C) solution of BBr3 (1 M, 8.4 mL, 8.4 mmol). The solution is warmed to 00C and is stirred for 3 h. The reaction is quenched carefully with methanol (1 mL) and washed with saturated NaHCO3 and then brine (25 mL each). The organic layer is dried over MgSO4, filtered and concentrated and the product is purified by CombiFlash.(R). Companion to give phenol 15f (530 mg, 80percent yield). |
80% | A solution of methyl ether 15e (720 mg, 4.2 mmol) in anhydrous CH2CI2 (20 mL) is added slowly to a precooled (-300C) solution of BBr3 (1 M, 8.4 mL, 8.4 mmol). The solution is warmed to O0C and is stirred for about 3 h. The reaction is quenched carefully with methanol (1 mL) and washed with saturated NaHCO3 and then brine (25 mL each). The organic layer is dried over MgSO4, filtered and concentrated and the product is purified by CombiFlash.(R). Companion to give phenol 15f (530 mg, 80percent yield). | |
80% | A solution of methyl ether 15e (720 mg, 4 2 mmol) in anhydrous CH2Cl2 (20 mL) is added slowly to a precooled (-300C) solution of BBr3 (1 M, 8 4 mL, 8 4 mmol) The solution is warmed to 0°C and is stirred for 3 h The reaction is quenched carefully with methanol (1 mL) and washed with saturated NaHCO3 and then brine (25 mL each) The organic layer is dried over MgSO4, filtered and concentrated and the product is purified by CombiFlash.(R). Companion to give phenol 15f (530 mg, 80percent yield) |
80% | A solution of methyl ether 15e (720 mg, 4.2 mmol) in anhydrous CH2CI2 (20 mL) is added slowly to a precooled (-300C) solution of BBr3 (1 M, 8.4 mL, 8.4 mmol). The solution is warmed to 0°C and is stirred for 3 h. The reaction is quenched carefully with methanol (1 mL) and washed with saturated NaHCO3 and then brine (25 mL <n="88"/>each). The organic layer is dried over MgSO4, filtered and concentrated and the product is purified by CombiFlash.(R). Companion to give phenol 15f (530 mg, 80percent yield). |
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