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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
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Structure of 69189-19-1
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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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CAS No. : | 69189-19-1 |
Formula : | C8H7Br3 |
M.W : | 342.85 |
SMILES Code : | BrCC1=CC(Br)=CC=C1CBr |
MDL No. : | MFCD16620247 |
InChI Key : | PJYGXPFKKAJUBG-UHFFFAOYSA-N |
Pubchem ID : | 12496465 |
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#: | 3261 |
Packing Group: | Ⅱ |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 59.81 |
TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.8 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.73 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.94 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
4.54 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.51 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.9 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.59 |
Solubility | 0.00887 mg/ml ; 0.0000259 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.42 |
Solubility | 0.13 mg/ml ; 0.000379 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.73 |
Solubility | 0.000641 mg/ml ; 0.00000187 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) |
Yes |
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 |
-5.74 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) |
2.16 |
* 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 phosphorus tribromide In diethyl ether at 0℃; for 7 h; Reflux | To a solution of 11 (103 mg, 0.474 mM) in Et2O (3 mL) was slowly added a solution of PBr3 (0.16 mL,1.66 mM) in Et2O (0.25 mL) at 0 °C. The whole was refluxed for 7 h, poured to ice (ca 30 mL), andextracted with Et2O (20 mL × 3). The organic solutions were washed with brine (10 mL), dried, andevaporated. Purification of the residue by column chromatography (SiO2, hexane) gave 12 (154 mg,95percent) as colorless plates, mp 42-44 °C (lit [20]. mp 40-44 °C). |
84% | With N-Bromosuccinimide In dichloromethane at 20℃; for 6 h; | After dissolving Compound 3 (5.2 g, 23.9 mmol) in methylene chloride (50 milliliter), followed by adding N-bromosuccinimide (12.8 g, 71.7 mmol) at room temperature, and then the resultant solution was stirred for 6 hours. Water (200 milliliter) was poured in the resultant reaction solution, and the deposited solid was washed by ethanol, and as a result, Compound 4 was obtained. Product Amount: 6.9 g, Yield: 84 percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 1 h; Heating / reflux | 4-bromo-l,2-bis(bromomethyl)benzene (Q22). To a 1000 mL round bottom flask was added 4-brmo-oe-xylene <21) (0.0811 mol, 15.0Og), NBS (0.0426 mol, 7.580 g), 2,2 -azobisisobutyronitrile (0.00405 mol, 0.6650 g) and 500 mL of CCl4. The reaction mixture was then heated under reflux for Ih. After this time another amount of NBS and AIBN was added and repeated over four times in total. The precipitate was filtered off from the warm reaction mixture and the filtrate concentrated. Crude material was crystallized from hexanes to form white crystals (23 g, 93percent). 1H NMR (300 MHz, CDCl3) δ 7.53 (d, IH, ArH, J=2.0 Hz), 7.44 (dd, IH, ArH, J-8.1 Hz, J =2.0 Hz), 7.24 (d, IH, ArH, J=8.10), 4.60 (d, 4H, CH2, J=4.20 Hz) |
56.7% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 70℃; for 1 h; | Step A : 4-bromo-l,2-bis(bromomethyl)benzene A solution of 4-bromo-l,2-dimethylbenzene (2.0 g, 10.81 mmol) in carbon tetrachloride (70 mL) in a 250 mL round bottom flask was stirred at room temperature until all solids were dissolved. N-bromosuccinimide (4.81 g, 27.0 mmol) and 2,2'- azobis(2-methylpropionitrile) (0.044 g, 0.270 mmol) were added and mixture was heated to 70°C for 1 h. After cooling to room temperature, the mixture was filtered through celite bed. Celite bed was rinsed with carbon tetrachloride (3x50 mL). Combined filtrate was dried (sodium sulphate), filtered and concentrated under reduced pressure. The crude material was purified by combi- flash column chromatography (Column: 120 gm Red- Sep; eluent: hexane). The fractions were collected and concentrated under reduced pressure to yield 4-bromo-l,2-bis(bromomethyl) benzene (2.1 g, 56.7percent yield) as colorless gummy oil. 1H NMR (400 MHz, CDC13): δ 7.56-7.51 (m, 1H), 7.44-7.41 (m, 1H), 7.25- 7.22 (m, 1H), 4.59 (s, 2H), 4.578 (s, 2H). |
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