Structure of 1-Fluoro-2-iodobenzene
CAS No.: 348-52-7
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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.
Synonyms: o-Iodofluorobenzene
4.5
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| CAS No. : | 348-52-7 |
| Formula : | C6H4FI |
| M.W : | 222.00 |
| SMILES Code : | FC1=CC=CC=C1I |
| Synonyms : |
o-Iodofluorobenzene
|
| MDL No. : | MFCD00001031 |
| InChI Key : | TYHUGKGZNOULKD-UHFFFAOYSA-N |
| Pubchem ID : | 67673 |
| GHS Pictogram: |
|
| Signal Word: | Danger |
| Hazard Statements: | H227-H302-H315-H318 |
| Precautionary Statements: | P210-P264-P270-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P332+P313-P362+P364-P370+P378-P403+P235-P501 |
| Class: | 9 |
| UN#: | 3082 |
| Packing Group: | Ⅲ |
| Num. heavy atoms | 8 |
| Num. arom. heavy atoms | 6 |
| Fraction Csp3 | 0.0 |
| Num. rotatable bonds | 0 |
| Num. H-bond acceptors | 1.0 |
| Num. H-bond donors | 0.0 |
| Molar Refractivity | 39.12 |
| TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.02 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.1 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.85 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.64 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.29 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.98 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-3.72 |
| Solubility | 0.0419 mg/ml ; 0.000189 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-2.77 |
| Solubility | 0.379 mg/ml ; 0.00171 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.63 |
| Solubility | 0.0516 mg/ml ; 0.000232 mol/l |
| Class? Solubility class: Log S scale |
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) |
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 |
-5.45 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) |
2.2 |
* 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 |
|---|---|---|
| 75% | With [ruthenium(II)(eta6-1-methyl-4-isopropyl-benzene)(chloride)(mu-chloride)]2; potassium carbonate; triphenylphosphine; In benzene; at 150℃; for 24h;Sealed tube; | General procedure: In a 30-mL sealed tube, <strong>[2622-63-1]1-methyl-2-phenylbenzimidazole</strong> (1, 0.25mmol), [RuCl2(p-cymene)]2 (0.0125 mmol), Ph3P (0.075 mmol),K2CO3 (0.50 mmol), and iodoarene (0.25 mmol) were combined inanhydrous benzene (2 mL) under air. The mixture was then stirredat 150 °C for 24 h. The mixture was cooled to r.t., diluted with EtOAc, and filtered through a small pad of Celite. The filtrate was concentrated in vacuo and purified by flash chromatography (silicagel, EtOAc?hexane) to give the analytically pure 2-(biphenyl-2-yl)benzimidazoles. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 69% | With carbon disulfide; cycl-isopropylidene malonate; triethylamine; copper(l) chloride; In N,N-dimethyl-formamide; at 100℃; for 4h;Inert atmosphere; | General procedure: A mixture of Meldrum?s acid (1 mmol) and Et3N (2 mmol) in DMF was stirred for 15 min at r.t. Then, CS2 (1 mmol) was added and stirred for 15 min. Then, the obtained mixture was added to a stirred solution of aryl halide (1 mmol) and CuCl (0.1 mmol) in DMF (2 ml), and heated at 100 C for 4h. When the reaction was completed (TLC), the mixture was extracted with CH2Cl2 (3 3ml) and H2O (3ml). The organic layer was separated and dried (Na2SO4) and the solvent was evaporated in vacuo to give the diaryl disulfide. The product was purified by column chromatography on silica gel (EtOAc / Petroleum ether, 1:4). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 87% | With triethylamine; In water; at 100℃; for 12h; | General procedure: In a typical Heck coupling reaction between iodobenzene and acrylic acid, 10 mmol of iodobenzene and 30 mmol of acrylic acid were mixed with 50 mmol of triethylamine and 10 mL of distill water. The insoluble PdIPN catalyst (2.3 g) was added to the solution, and the reactants were heated in an oil bath at 100 C for 12 h under stirring. After the reaction, the catalysts were filtered, thoroughly washed with water and ethanol (at least three times) and dried in the air for the next round of use. The white product was precipitated out by adding 1 mol/L HCl solution, then separated by centrifugation and filtration, washed repeatedly with cold water, and dried in vacuum for 6 h. The yield from the reaction between iodobenzene and acrylic acid was 87%. |