Structure of 156001-51-3
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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'.
Search for reports by entering the product batch number.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 156001-51-3 |
Formula : | C8H6BrN |
M.W : | 196.04 |
SMILES Code : | BrC1=CC(=C(C=C1)C)C#N |
MDL No. : | MFCD08061920 |
InChI Key : | WNVUTFDOGUGEIS-UHFFFAOYSA-N |
Pubchem ID : | 12994004 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 43.82 |
TPSA ? Topological Polar Surface Area: Calculated from |
23.79 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.16 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.7 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.63 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.52 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.94 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.59 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.2 |
Solubility | 0.124 mg/ml ; 0.00063 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.85 |
Solubility | 0.275 mg/ml ; 0.0014 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.73 |
Solubility | 0.0368 mg/ml ; 0.000188 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) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.58 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 |
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 |
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) |
1.86 |
* 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 |
---|---|---|
77% | Example 22 5-Bromo-2-methylbenzonitrile Water (13.5 mL), HBr (74%, 14.4 mL) and <strong>[50670-64-9]5-amino-2-methylbenzonitrile</strong> (2.0 g, 15.1 mmol) dissolved in water (24 mL) was added to a flask and heated to 50 C. for 20 min. Then the mixture was cooled to 0~5 C., and a solution of NaNO2 (1.2 g, 17.4 mmol) in water was added. The reaction mixture was stirred for 10 min at 0~5 C., then was warmed to 40 C. A solution of CuBr (6.5 g, 45.1 mmol) in water (36 mL) and HBr (7.2 mL) was added to the mixture, and refluxed for 2 h. The mixture was extracted with AcOEt, and the organic layer was washed by saturated NaHCO3 solution and brine, and dried over Na2SO4. The crude product was purified by flask chromatograph (PE:EA=50:1), obtaining 2.3 g of 5-bromo-2-methylbenzonitrile as a white solid (yield: 77%). 1H NMR (400 MHz, CDCl3) delta 7.72 (s, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.19 (d, J=8.0 Hz, 1H), 2.51 (s, 3H). | |
77% | Example 22 5-Bromo-2-methylbenzonitrile Water (13.5 mL), HBr (74%, 14.4 mL) and <strong>[50670-64-9]5-amino-2-methylbenzonitrile</strong> (2.0 g, 15.1 mmol) dissolved in water (24 mL) was added to a flask and heated to 50 C. for 20 min. Then the mixture was cooled to 0~5 C., and a solution of NaNO2 (1.2 g, 17.4 mmol) in water was added. The reaction mixture was stirred for 10 min at 0~5 C., then was warmed to 40 C. A solution of CuBr (6.5 g, 45.1 mmol) in water (36 mL) and HBr (7.2 mL) was added to the mixture, and refluxed for 2 h. The mixture was extracted with AcOEt, and the organic layer was washed by saturated NaHCO3 solution and brine, and dried over Na2SO4. The crude product was purified by flask chomatograph (PE:EA=50:1), obtaining 2.3 g of 5-bromo-2-methylbenzonitrile as a white solid (yield: 77%). 1H NMR (400 MHz, CDCl3) delta 7.72 (s, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.19 (d, J=8.0 Hz, 1H), 2.51 (s, 3H). | |
77% | Example 25 5-Bromo-2-methylbenzonitrile Keep the solution of <strong>[50670-64-9]5-amino-2-methylbenzonitrile</strong> (2.0 g, 15.1 mmol) dissolved in water (24 mL) and HBr (74%, 14.4 mL) stirring for 20 min, then the mixture was cooled to 0~5 C., and the solution of NaNO2 (1.2 g, 17.4 mmol) in water (13.5 mL) was added. The reaction mixture was stirred for 10 min at 0~5 C., then was warmed to 40 C. A solution of CuBr (6.5 g, 45.1 mmol) in water (36 mL) and HBr (7.2 mL) was added to the mixture, and it was stirred for 2 h. The mixture was extracted with AcOEt, and the organic layer was washed with saturated NaHCO3 solution, brine, and dried over Na2SO4. The crude product was purified by flask chromatograph (PE:EA=50:1), obtaining 2.3 g of 5-bromo-2-methylbenzonitrile as a white solid (Yield: 77%). 1H NMR (400 MHz, CDCl3): delta 7.72 (s, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.19 (d, J=8.0 Hz, 1H), 2.51 (s, 3H). |
77% | With sulfuric acid; hydrogen bromide; copper(I) bromide; sodium nitrite; In water; acetic acid; at 16 - 40℃; for 0.75h; | Step 3: 5-Bromo-2-methylbenzonitrile: Conc. sulfuric acid (60 mL) is added to sodium nitrite (5.75 g, 83.4 mmol). The temperature rises to 70C and solution is effected. After cooling to 20-40C, the above solution is added dropwise to a mechanically stirred solution of 5-amino- 2-methylbenzonitrile (10.0 g, 75.8 mmol) in acetic acid (150 mL). The temperature is maintained at 20-40C throughout the addition. The reaction mixture is cooled to 16-20C and a solution of cuprous bromide (24 g, 167 mmol) in conc. hydrobromic acid (150 mL) is added keeping the temperature between 16-20C. After 45 min, the reaction mixture is poured onto ice (500 g) and the solids are collected by filtration then dissolved in dichloromethane (600 mL), washed with brine, dried, filtered and concentrated to give 5-bromo-2-methylbenzonitrile (see also, Dressler, J. et al. EP 0 594 019) (11.5 g, 77%) as a brown solid. ¹H NMR (CDC13, 8 ppm) : 7.72 (lH, s), 7.60 (1H, dd), 7.20 (1H, dd), 2.50 (3H, s). |
77% | Example 22 5-Bromo-2-methylbenzonitrileWater (13.5 mL), HBr (74%, 14.4 mL) and <strong>[50670-64-9]5-amino-2-methylbenzonitrile</strong> (2.0 g, 15.1 mmol) dissolved in water (24 mL) was added to a flask and heated to 50 C for for 20 min. Then the mixture was cooled to 0-5 0C, and a solution OfNaNO2 (1.2 g, 17.4 mmol) in water was added. The reaction mixture was stirred for 10 min at 0-5 C, then was warmed to 40 C. A solution of CuBr (6.5 g, 45.1 mmol) in water (36 mL) and HBr (7.2 mL) was added to the mixture, and refluxed for 2 h. The mixture was extracted with AcOEt, and the organic layer was washed by saturated NaHCtheta3 solution and brine, and dried over Na2SOphi The crude product was purified by flask chomatograph (PE:EA=50: 1), obtaining 2.3 g of 5-bromo-2-methylbenzonitrile as a white solid (yield: 77%). 1H NMR (400 MHz, CDCl3) delta 7.72 (s, 1 H), 7.59 (d, J=8.0 Hz, 1 H), 7.19 (d, J=8.0 Hz, 1 H), 2.51 (s, 3 H). |