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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+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 100+ |
Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Structure of 81998-05-2
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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. : | 81998-05-2 |
Formula : | C12H11BrN2 |
M.W : | 263.13 |
SMILES Code : | CC1=CC(=NC=C1)C1=NC=CC(CBr)=C1 |
MDL No. : | MFCD08275265 |
InChI Key : | HUJZHWSADZZJAB-UHFFFAOYSA-N |
Pubchem ID : | 10956379 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H290-H314 |
Precautionary Statements: | P234-P260-P264-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P390-P405-P406-P501 |
Class: | 8 |
UN#: | 3261 |
Packing Group: | Ⅲ |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.17 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 65.27 |
TPSA ? Topological Polar Surface Area: Calculated from |
25.78 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.69 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.4 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.2 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.89 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.94 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.82 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.44 |
Solubility | 0.0948 mg/ml ; 0.00036 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.58 |
Solubility | 0.687 mg/ml ; 0.00261 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.82 |
Solubility | 0.000402 mg/ml ; 0.00000153 mol/l |
Class? Solubility class: Log S scale |
Moderately 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) |
Yes |
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 |
-6.2 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 |
0.0 |
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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.44 |
* 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 |
---|---|---|
91.3% | With sulfuric acid; hydrogen bromide; In water; for 40h;Reflux; | A solution of 15(301 mg, 1.50 mmol) in 48% aqueous HBr solution (15 mL) andconcentrated H2SO4 (0.6 mL) was refluxed for 40 h. Aftercooling to room temperature, water (4 mL) was added to thereaction mixture and basified with sat. aqueous Na2CO3 solutionto pH 8. The aqueous solution was extracted with CH2Cl2 until the organic layer wascolorless. The combined organic layer was dried over anhydrous Na2SO4 andconcentrated. The residue was purified by silica gel column chromatography withchloroform / triethylamine (v/v, 40/1) to give 16 (361 mg, 1.37 mmol, 91.3%) as lightbrown . 1H NMR (CDCl3): = 8.66 (d, J = 5.1 Hz, 1H), 8.55 (d, J = 4.8 Hz, 1H), 8.41 (s, 1H),8.24 (s, 1H), 7.34 (dd, J1 = 5.1 Hz, J2 = 1.8 Hz, 1H), 7.16 (d, J = 4.8 Hz, 1H), 4.48 (s,2H), 2.45 (s, 3H). IR (NaCl): = 2918, 1632, 1597, 1567, 1517, 1444, 1379, 1038, 994,827, 749 cm-1 |
In dichloromethane; | (c) 4-bromomethyl-4'-methyl-2,2'-bipyridine To a solution of crude 4-hydroxymethyl-4'-methyl-2,2'-bipyridine in methylene chloride at 0 C. were added a slight excess of both PPh3 and N-bromosuccinimide to immediately give a brown-orange solution. The mixture was stirred for 1 h, warmed to room temperature, and concentrated to a thick brown oil. Chromatography on silica with 1:1 hexanes:diethyl ether as eluent gave the product as a white powder. Yields 50%. 1H NMR spectra are consistent with structure. | |
(d) Preparation of 4-methyl-4'-bromomethyl-2,2'-bipyridine 1.5 g of 4-methyl-4'-hydroxymethyl-2,2'-bipyridine are reacted analogously to Example 2(e). This gives 1.74 g (88% of theory) of 4-methyl-4'-bromomethyl-2,2'-bipyridine as an unstable oil which is used immediately for the further reaction. |
In dichloromethane; | (c) 4-bromomethyl-4'-methyl-2,2'-bipyridine To a solution of crude 4-hydroxymethyl-4'-methyl-2,2'-bipyridine in methylene chloride at 0 C. were added a slight excess of both PPh3 and N-bromosuccinimide to immediately give a brown-orange solution. The mixture was stirred for 1 h, warmed to room temperature, and concentrated to a thick brown oil. Chromatography on silica with 1:1 hexanes:diethyl ether as eluent gave the product as a white powder. Yields 50%. 1H NMR spectra are consistent with structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methylamine; In tetrahydrofuran; | (d) 4-methylaminomethyl-4'-methyl-2,2'-bipyridine Methylamine was bubbled slowly through a solution of <strong>[81998-05-2]4-bromomethyl-4'-methyl-2,2'-bipyridine</strong> in THF for 10 min at 0 C. to give a white precipitate and a colorless solution. After bubbling, the solution was stirred for another hour at room temperature. The reaction was pumped dry to a pale off-white wax. The wax was extracted with diethyl ether and pumped dry to a pale yellow oil. Yields 80%. 1H NMR spectra are consistent with structure. | |
With methylamine; In tetrahydrofuran; | (d) 4-methylaminomethyl-4'-methyl-2,2'-bipyridine Methylamine was bubbled slowly through a solution of <strong>[81998-05-2]4-bromomethyl-4'-methyl-2,2'-bipyridine</strong> in THF for 10 min at 0 C. to give a white precipitate and a colorless solution. After bubbling, the solution was stirred for another hour at room temperature. The reaction was pumped dry to a pale off-white wax. The wax was extracted with diethyl ether and pumped dry to a pale yellow oil. Yields 80%. 1H NMR spectra are consistent with structure. |