Structure of 217-59-4
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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. : | 217-59-4 |
Formula : | C18H12 |
M.W : | 228.29 |
SMILES Code : | C12=CC=CC=C1C3=CC=CC=C3C4=CC=CC=C24 |
MDL No. : | MFCD00001108 |
InChI Key : | SLGBZMMZGDRARJ-UHFFFAOYSA-N |
Pubchem ID : | 9170 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H318-H410 |
Precautionary Statements: | P273-P280-P305+P351+P338 |
Class: | 9 |
UN#: | 3077 |
Packing Group: | Ⅲ |
Num. heavy atoms | 18 |
Num. arom. heavy atoms | 18 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 78.96 |
TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.66 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
5.49 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
5.15 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
5.97 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
5.09 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
4.87 |
Log S (ESOL):? ESOL: Topological method implemented from |
-5.45 |
Solubility | 0.000802 mg/ml ; 0.00000351 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-5.25 |
Solubility | 0.00129 mg/ml ; 0.00000565 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-7.43 |
Solubility | 0.00000846 mg/ml ; 0.0000000371 mol/l |
Class? Solubility class: Log S scale |
Poorly 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 |
-3.79 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 |
1.0 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) |
1.0 |
* 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 |
---|---|---|
95% | With bromine; iron; In nitrobenzene; at 20 - 205℃; for 18.25h; | To a solution of triphenylene (1, 1.07 g, 4.7 mmol) in nitrobenzene (40 mL) with iron powder (100 mg, 1.79 mmol) bromine (2.2 mL, 38.8 mmol) was slowly added over 15 minutes. The solution was then allowed to stand for 16 hours at room temperature. It was heated at 205 C for 2 hours. The mixture was cooled to room temperature and mixed with diethyl ether (150 mL) and filtered. The crude white solid was washed by diethyl ether (3x30 mL) and acetone (3x10 mL). After drying in vacuo for 12 hours, 3.13 g of 2,3,6,7, 10,11-hexabromotriphenylene (yield 95%) was collected. The product was used directly without characterization due to low solubility. |
94.8% | With bromine; iron; In nitrobenzene; at 20 - 210℃; for 3.33h;Inert atmosphere; | Under nitrogen, bromine (9.0 mL, 349 mmol) was added dropwise to 9 (3.95 g, 17.3 mmol) and Fe (410 mg, 7.34 mmol) in nitrobenzene (200 mL) with stirring at rt for 20 min and furthermore at 210 C for 3 h. After cooling the reaction mixture to room temperature, Et2O was added and the precipitate was collected. The solid was washed thoroughly with Et2O, acetone, and CHCl3 to give white powder (11.5 g, 16.4 mmol, 94.8%). M.p. >300 C; 1HNMR (300 MHz, CDCl3): delta (ppm) = 8.72 (s, 6H, Ar-H); IR (KBr): numax(cm-1) = 1585, 1551, 1454, 1365, 1119, 873, 863. |
84% | With bromine; iron; at 170℃; for 10h;Inert atmosphere; | 5.0 g of triphenylene, 0.49 g of iron powder and 10.1 ml of bromine were added to a reaction vessel purged with nitrogen and heated, followed by stirring at 170 C. for 10 hours. After cooling to room temperature, 100 ml of tetrahydrofuran was added and the mixture was further stirred for 0.5 hour. Filtration gave 2, 3, 6, 7, 10, 11-hexabromotriphenylene gray powder13.5 g (yield 84%) was obtained. |
80% | With bromine; iron; In nitrobenzene; | Step a) [0222] Triphenylene (1 equivalent) is brominated with 8 equivalents of Br2 in the presence of catalytic amounts of iron in nitrobenzene to obtain 80% brominated triphenylene derivative. |