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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
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Structure of 175018-77-6
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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.
4.5
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CAS No. : | 175018-77-6 |
Formula : | C8H7BrF2 |
M.W : | 221.04 |
SMILES Code : | FC1=CC(CCBr)=CC=C1F |
MDL No. : | MFCD12025017 |
InChI Key : | XCKJCCCKEWTUIV-UHFFFAOYSA-N |
Pubchem ID : | 15020053 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H302-H314 |
Precautionary Statements: | P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501 |
Class: | 8 |
UN#: | 1760 |
Packing Group: | Ⅲ |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 44.0 |
TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.44 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.14 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.74 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
4.25 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.99 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.51 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.46 |
Solubility | 0.0766 mg/ml ; 0.000347 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.81 |
Solubility | 0.343 mg/ml ; 0.00155 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.62 |
Solubility | 0.00524 mg/ml ; 0.0000237 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 |
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) |
Yes |
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 |
-5.42 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 |
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) |
1.96 |
* 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 |
---|---|---|
In toluene; | Preparation of (3,4-difluorophenyl)ethyltriphenylphosphonium bromide A mixture of 19.67 g (89 mmol) of 3,4-difluoro-phenethyl bromide, 28.07 g (107 mmol) of triphenyl phosphine and 134 ml of toluene was heated under reflux for 36 hrs. After cooling, the crystal was washed by decantation with toluene and dried in vacuo, while ice-cooling. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium bicarbonate; sulfuric acid; hydrogen bromide; | Preparation of 3,4-difluorophenethylbromide 17.59 g (111 mmol) of 2-(3,4-difluorophenyl)ethanol, 16 ml (137 mmol) of hydrogen bromide, 6.8 ml (234 mmol) of conc. sulfuric acid were added in the order, and the mixture was heated under reflux for 3 hrs. The reaction mixture was poured onto an ice-bath, an organic layer and an aqueous layer were separated, the aqueous layer was extracted with ether, the extract combined with the organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate. The solvent was distilled off, the solution condensed and purified by vacuum distillation to obtain 21.96 g (bp 68-70 C./2-4 Torr.) of oily product. The oily product was purified by column chromatography (elution solvent: hexane:ethyl acetate=3:1), the elude was further purified by vacuum distillation to obtain 19.79 g of the title compound (81%, bp 73-75 C./4 Torr.) as oily product. | |
With sulfuric acid; hydrogen bromide; In acetic acid; at 100.0℃; for 4.0h; | A mixture of 2-(3,4-difluorophenyl)ethanol (5 g, 0.032 mol; see step (iii) above), HBr in acetic acid (51.84 mL of 49%, 0.64 mol) and 5 mL of sulfuric acid was stirred at 1000C for 4 h. The reaction mixture was poured onto ice and extracted with diethylether. The organic layer was washed with NaHCO3 and water and then dried over sodium sulfate. Solvent evaporation under reduced pressure, followed <n="90"/>by purification (three times) over silica gel (using petroleum ether as eluent), afforded 1.8 g of the title compound as a liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
a 3,4-(Difluoro)phenethyl bromide Prepared from 3,4-(difluoro)phenylacetic acid using the procedures described for Intermediate 3. delta (250 MHz, CDCl3) 3.12 (2H, t, J=7.3 Hz, CH2), 3.54 (2H, t, J=7.3 Hz, CH2), 6.90-7.16 (3H, m, Ar--H). |
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