Structure of 328-70-1
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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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Qing Yun Li ; Leigh Anna Hunt ; Kalpani Hirunika Wijesinghe ; Christine Curiac ; Ashley Williams ; Amala Dass , et al.
Abstract: Strong photoinduced oxidants are important to organic synthesis and solar energy conversion, to chemical fuels or electric. For these applications, visible light absorption is important to solar energy conversion and long-lived excited states are needed to drive catalysis. With respect to these desirable qualities, a series of five 5,6-dicyano[2,1,3]benzothiadiazole (DCBT) dyes are examined as organic chromophores that can serve as strong photooxidants in catalytic systems. The series utilizes a DCBT core with aryl groups on the periphery with varying electron donation strengths relative to the core. The dyes are studied via both steady-state and transient absorption and emission studies. Additionally, computational analysis, voltammetry, crystallography, and absorption spectroelectrochemistry are also used to better understand the behavior of these dyes. Ultimately, a strong photooxidant is arrived at with an exceptionally long excited state lifetime for an organic chromophore of 16 µs. The long-lived excited state photosensitizer is well-suited for use in catalysis, and visible light driven photosensitized water oxidation is demonstrated using a water-soluble photosensitizer.
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Purchased from AmBeed: 54512-79-7 ; 5798-75-4 ; 328-70-1 ; 586-76-5 ; 22385-77-9 ; 3109-63-5 ; 23783-42-8 ; 3375-31-3 ; 1122-58-3 ; 479094-62-7 ; 75-98-9 ; 51364-51-3 ; 538-75-0 ; 584-08-7 ; 1122-91-4 ; 123-30-8 ; 108-88-3 ; 109-77-3 ; 64-19-7 ; 603-35-0
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| CAS No. : | 328-70-1 |
| Formula : | C8H3BrF6 |
| M.W : | 293.00 |
| SMILES Code : | C1=C(C(F)(F)F)C=C(C=C1C(F)(F)F)Br |
| MDL No. : | MFCD00000381 |
| InChI Key : | CSVCVIHEBDJTCJ-UHFFFAOYSA-N |
| Pubchem ID : | 67602 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H315-H319-H335 |
| Precautionary Statements: | P261-P305+P351+P338 |
| Num. heavy atoms | 15 |
| Num. arom. heavy atoms | 6 |
| Fraction Csp3 | 0.25 |
| Num. rotatable bonds | 2 |
| Num. H-bond acceptors | 6.0 |
| Num. H-bond donors | 0.0 |
| Molar Refractivity | 44.15 |
| TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.45 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.94 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
6.79 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
5.08 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.6 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
4.77 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-4.93 |
| Solubility | 0.00342 mg/ml ; 0.0000117 mol/l |
| Class? Solubility class: Log S scale |
Moderately soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-4.68 |
| Solubility | 0.00616 mg/ml ; 0.000021 mol/l |
| Class? Solubility class: Log S scale |
Moderately soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.01 |
| Solubility | 0.00284 mg/ml ; 0.00000968 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 |
-4.58 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 |
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) |
1.74 |
* 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.

[ 1293-65-8 ]
[ 328-70-1 ]


[ 328-70-1 ]
[ 116838-52-9 ]

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 57% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In dichloromethane; water; at 60℃; | General procedure: All liquids incorporated into the reaction were degassed prior to addition. To a solution of 1 (1 eq., 50.0 mg, 0.192 mmols) and PdCl2(dppf)•CH2Cl2 (20 mol%, 31.3 mg, 0.0384 mmols) in CH2Cl2 (0.1M, 1.6 mL) was added aryl bromide (1.1 eq., 0.211 mmols) and 3.33M K2CO3 solution (6 eq.,0.958 mmols, 0.27 mL). The mixture is quickly stirred and heated at 60. The mixture would go from a bright red solution to a darkened mixture within minutes of the reaction. Upon confirmation of completion by TLC (typically eluted with 40% to 50% MeCN/CH2Cl2), the mixture is immediately taken off the heat and diluted with 10 mL H2O. The organic mixture is extracted with 3 x 10 mL diethyl ether. The organic extracts are dried over Na2SO4, filtered then concentrated. The crude product is purified by silica gel column chromatography (gradient with ethylacetate/hexanes) to afford 3 as a resin or white powder. |

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