Structure of 63089-50-9
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 63089-50-9 |
Formula : | C9H6N2 |
M.W : | 142.16 |
SMILES Code : | CC1=CC=C(C#N)C(=C1)C#N |
MDL No. : | MFCD02093739 |
InChI Key : | MDXGRFMFORMPGT-UHFFFAOYSA-N |
Pubchem ID : | 2733971 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302+H312+H332 |
Precautionary Statements: | P280 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.11 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 40.84 |
TPSA ? Topological Polar Surface Area: Calculated from |
47.58 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.64 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.72 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.74 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.08 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.24 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.68 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.21 |
Solubility | 0.879 mg/ml ; 0.00619 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.34 |
Solubility | 0.657 mg/ml ; 0.00462 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.93 |
Solubility | 0.167 mg/ml ; 0.00117 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) |
Yes |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.95 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 |
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) |
1.41 |
* 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 |
---|---|---|
70% | With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;Reflux; | (1) Weigh 10 g (0.07 mol) of 4-methyl phthalonitrile and add it to a 1 L three-necked round bottom flask.A further 250 mL of a carbon tetrachloride solution was added to a three-neck round bottom flask.0.2g of BPO (dibenzoyl peroxide) is added in batches,13.8 g (0.077 mol) of NBS (N-bromosuccinimide in batches) was slowly warmed to the carbon tetrachloride reflux temperature,With the progress of the reaction system has a white solid,Reflux reaction 20-24 hours, suction filtration,The solvent was removed by spin-drying to give 10.78 g of a pale yellow solid product.Yield 70%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With butyl(2-hydroxyethyl)dimethylammonium acetate; at 100℃; for 2.5h;Inert atmosphere; Ionic liquid; | General procedure: A mixture of phthalonitrile (4a-g, 200 mg) and functional ionic liquid 2c (1 equivalent) was stirred at 100C under a nitrogen atmosphere for the appropriate time (Table 4). The progress of the reaction was monitored by TLC and UV-Visible spectroscopic analysis. When reaction was completed, the mixture was cooled to room temperature, and distilled water (50 mL) was added to dissolve the functional ionic liquid. The blue-green solid mass was filtered and the aqueous filtrate was evaporated under reduced pressure to recover the ionic liquid pure enough for further use. The solid mass was further washed thoroughly with H2O-MeOH (1:1, 100 mL) to remove the impurities and phthalocyanines are obtained in pure form. All of the phthalocyanines are known compounds and their purities were confirmed by comparison with literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With butyl(2-hydroxyethyl)dimethylammonium acetate; at 100℃; for 2h;Ionic liquid; Inert atmosphere; | General procedure: A mixture of desired phthalonitrile (4a-i, 200mg) and corresponding metal salts (0.25 equivalents) were stirred at 100C with functional ionic liquid 2c (1 equivalent) for the appropriate time (Table 1, 2 and 3). The progress of the reaction was monitored by TLC and UV-Visible spectroscopic analysis. When reaction was completed, the mixture was cooled to room temperature, and distilled water (50 mL) was added to dissolve the functional ionic liquid. The blue-green solid mass was filtered and the aqueous filtrate was evaporated using reduced pressure to recover the pure ionic liquid for further use. The solid mass was further washed thoroughly with H2O-MeOH (1:1, 100 mL) to remove the colorless impurities and metallophthalocyanines are obtained in pure form. All of the phthalocyanines are known compounds and their purities were confirmed by UV-Visible spectroscopic analysis and further comparison with literature. |
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