Structure of 320-31-0
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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. : | 320-31-0 |
Formula : | C8H4BrF3O2 |
M.W : | 269.02 |
SMILES Code : | BrC1=CC(=C(C(=O)O)C=C1)C(F)(F)F |
MDL No. : | MFCD07787468 |
Boiling Point : | No data available |
InChI Key : | JXHWAPDBDXPBEQ-UHFFFAOYSA-N |
Pubchem ID : | 25067392 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 5.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 46.1 |
TPSA ? Topological Polar Surface Area: Calculated from |
37.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.59 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.02 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.32 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.38 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.95 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.05 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.6 |
Solubility | 0.0683 mg/ml ; 0.000254 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.47 |
Solubility | 0.0915 mg/ml ; 0.00034 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.51 |
Solubility | 0.0831 mg/ml ; 0.000309 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 |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.56 |
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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.64 |
* 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 |
---|---|---|
90% | With hydrogenchloride;Reflux; | H10) 4-Bromo-2-trifluoromethyl-benzoic acid methyl ester A solution of compound H9 (25.0 g, 94 mmol) in HCl-MeOH (250 mL) was refluxed overnight. TLC showed the starting material was consumed completely. The MeOH was evaporated in vacuo. And the resulting reside was partitioned between saturated NaHCO3 and EtOAc. The organic layer was dried over anhydrous Na2SO4 and concentrated under vacuum to give product H10 (23.5 g; 90.0percent). |
85% | With thionyl chloride; at 60℃; for 12.0h; | Synthesis of methyl 4-bromo-2-(trifluoromethyl)benzoate (107): 4-Bromo-2- (trifluoromethyl)benzoic acid (106; 1.6 g, 5.95 mmol) was dissolved in 20 mL of MeOH. 2 mL of SOd2 was added slowly. After the addition, the mixture was stirred at 60 °C for 12 h and concentrated. 20 mL of EtOAc was added to the residue. The mixture was washed with NaHCO3 aqueous solution, brine, dried over anhydrous Na2504 and concentrated to afford 1.6 g of methyl 4-bromo-2-(trifluoromethyl)benzoate 107 as yellow liquid. Yield (85percent). LCMS: m/z 282.7 [M+H], tR = 1.79 min |
25.8 g | With thionyl chloride; at 0℃; for 18.0h;Reflux; | Example 222: 4,5-Dihydr6xy-2-(4-methyI-2-(trifluoromethyl)benzyI)isophthalonitrile Methyl 4-bromo-2-(trifltioromethyl)benzoate 4-Bromo-2-trifluoromethyl benzoic acid (25 g) was dissolved in methanol (300 ml) and cooled to 0 °C. Thionyl chloride (88.8 g) was added and the mixture was refluxed for 18 h. The reaction mixture was concentrated under vacuum. Yield 25.8 g 1H NMR (400 MHz, chloroform-d) ppm 7.89 (d, 7=1.6 Hz, 1 H) 7.75 (dd, 7=8.0, 1.6 Hz, 1 H) 7.68 (d, 7=8.0 Hz, 1 H) 3.93 (s, 3 H) |
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