Structure of 30071-93-3
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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. : | 30071-93-3 |
Formula : | C10H6F6O |
M.W : | 256.14 |
SMILES Code : | CC(C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1)=O |
MDL No. : | MFCD00009910 |
InChI Key : | MCYCSIKSZLARBD-UHFFFAOYSA-N |
Pubchem ID : | 121616 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 17 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.3 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 7.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 46.64 |
TPSA ? Topological Polar Surface Area: Calculated from |
17.07 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.17 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.93 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
6.23 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.78 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.3 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
4.08 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.97 |
Solubility | 0.0276 mg/ml ; 0.000108 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.99 |
Solubility | 0.0263 mg/ml ; 0.000103 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.51 |
Solubility | 0.00792 mg/ml ; 0.0000309 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
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) |
Yes |
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 |
-5.07 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 |
1.0 |
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 |
0.0 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) |
1.48 |
* 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 |
---|---|---|
63% | With dihydrogen peroxide; trifluoroacetic anhydride; In chloroform; water; at 0 - 70℃; for 6.5h; | A mixture of 100 g (0.39 mol) of 3,5-bis(trifluoromethyl)acetophenone obtained above, 155.2 g of (0.74 mol) of trifluoroacetic anhydride and 400 ml of chloroform was stirred at 0°C in a nitrogen atmosphere. After adding 19.7 g (0.52 mol) of a 90percent hydrogen peroxide aqueous solution from a dropping funnel over 30 min and stirring the mixture for one our, the temperature was raised to 70°C to proceed the reaction for 5 h. After completion of the reaction, the temperature was returned to room temperature. The reaction product solution was poured into a separating funnel containing a saturated brine and washed with water. The organic phase separated was analyzed by gas chromatography. It was confirmed that 57.5 g (0.25 mol) of the aimed 3,5-bis(trifluoromethyl)phenol was produced (yield: 67percent). By vacuum distillation, 53.3 g (0.23 mol) of 3,5-bis(trifluoromethyl)phenol was isolated (yield: 63percent). The purity determined by gas chromatography was 99percent or higher. The results of ICP total elements analysis showed that none of Li, Na, K, Mg, Ca, Sr, Ba, Sc, Y, Ti, Zr, V, Nb, Cr, Mo, W, Mn, Fe, Ru, Co, Rh, Ni, Pd, Pt, Cu, Ag, Au, Zn, Cd, Al, In, Si, Sn, Pb, P, Sb and S were detected, and the content of each of group 1 and group 2 elements was 1 ppm or lower. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With potassium hydroxide; In ethanol; dichloromethane; water; at 20℃; | The 768mg (3mmol) 3,5- two trifluoromethyl acetophenone, 160mg (4mmol) sodium hydroxide was placed in 100mLSingle neck flask was added 10 drops of water, 20 mL of ethanol and dissolved; the 813mg (3mmol) 4- (9- (9H- carbazoleYl)) benzaldehyde was dissolved in 10mL of dichloromethane, ethanol and added dropwise to the mixture, stirred overnight at room temperature, overFiltered, ethanol, washed with petroleum ether, and dried to give a yellow solid (LJZ-5-31) 956mg, Yield = 63%. |
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