Structure of 89634-75-3
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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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CAS No. : | 89634-75-3 |
Formula : | C7H3ClF4 |
M.W : | 198.55 |
SMILES Code : | FC(C1=CC(F)=CC=C1Cl)(F)F |
MDL No. : | MFCD07782058 |
InChI Key : | CBMMVERXHJUMCM-UHFFFAOYSA-N |
Pubchem ID : | 13609145 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 36.41 |
TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.14 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.25 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
5.07 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
4.37 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.91 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.95 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.05 |
Solubility | 0.0176 mg/ml ; 0.0000886 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.96 |
Solubility | 0.0217 mg/ml ; 0.000109 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.18 |
Solubility | 0.013 mg/ml ; 0.0000656 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) |
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 |
-4.49 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
1.0 |
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 |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.47 |
* 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 hydrogenchloride; tetrafluoroboric acid; sodium nitrite; In water; ethyl acetate; | EXAMPLE S 1-Chloro-4-fluoro-2-(trifluoromethyl)benzene 4-Chloro-3-(trifluoromethyl)benzenamine (19.5 g, 100 mmoles), water (40 ml) and c.hydrochloric acid (40 ml) were heated with stirring on a steam bath until a white solid formed. The mixture was cooled (ice-salt bath) and a solution of sodium nitrite (7 g, 101 mmoles) in water (15 ml) was added over 15 mins. After stirring for a further hour at 0, tetrafluoroboric acid (30 g of 40% aqueous solution) was added dropwise over 15 minutes. After one hour the solid was filtered off, washed with water (10 ml), methanol (30 ml) and ether (30 ml) and then dried in vacuo. The dry compound was heated at 140-180 until no more fumes were observed. The cooled residue was dissolved in ethyl acetate, washed with 5% aqueous sodium hydroxide, dried Na2 SO4) and the solvent was removed in vacuo. The residue was distilled in vacuo (12 mmHg, oven temperature 50-55) to give the sub-title compound as a colourless oil (7.5 g). M+ 200/198; nmr (CDCl3)delta7.8-7.2 (m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In dimethyl sulfoxide; | EXAMPLE 13 Approximately 20 parts of <strong>[89634-75-3]2-chloro-5-fluorobenzotrifluoride</strong> is reacted with 14 parts of powdered potassium hydroxide (85%) in dimethylsulfoxide solvent at a temperature of about 60-70 C. for 12 to 16 hours to form 4-chloro-3-trifluoromethylphenolate. The reaction mixture is cooled, poured into iced water, and acidified with concentrated hydrochloric acid. The aqueous mixture is then extracted with methylene chloride and the organic layer dried and concentrated to recover 4-chloro-3-trifluoromethylphenol. |
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