Structure of 52414-97-8
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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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CAS No. : | 52414-97-8 |
Formula : | C7H6BrNO2 |
M.W : | 216.03 |
SMILES Code : | O=[N+](C1=C(C)C=CC=C1Br)[O-] |
MDL No. : | MFCD02673631 |
Boiling Point : | No data available |
InChI Key : | XDKMDDOCVPNVMB-UHFFFAOYSA-N |
Pubchem ID : | 142929 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H312-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 47.93 |
TPSA ? Topological Polar Surface Area: Calculated from |
45.82 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.78 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.79 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.67 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.77 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.8 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.16 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.27 |
Solubility | 0.115 mg/ml ; 0.000531 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.41 |
Solubility | 0.0843 mg/ml ; 0.00039 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.02 |
Solubility | 0.204 mg/ml ; 0.000946 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 |
-5.64 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 |
2.0 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) |
1.8 |
* 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 |
---|---|---|
42% | A mixture of tellurium (21.6 g, 169.4 mmol) and NaBH4 (15.0 g, 396 mmol) in 575 mL of absolute EtOH was heated at reflux under an atmosphere of N2 for 1 hr, then allowed to cool to rt. A solution of 3-bromo-2-nitrotoluene (1c; 7.32 g, 33.8 mmol) in 25 mL EtOH was added all at once and the mixture stirred at room temp for 2 hrs. The reaction mixture was filtered through a CELITE pad and the filtrate evaporated under reduced pressure. The residue was taken up in Et2O (about 200 mL), washed with brine then dried over MgSO4. Evaporation of the solvent afforded 2.66 g (42%) of 2a as a dark liquid. | |
42% | step 2 2-BROMO-6-METHYLANILINE (2a) -A mixture of tellurium (21.6 g, 169.4 mmol) and NaBH4 (15.0 g, 396 mmol) in 575 mL of absolute ETOH was heated at reflux under an atmosphere of N2 for 1 hr, then allowed to cool to rt. A solution of 3-bromo-2- nitrotoluene (LC ; 7.32g, 33.8 mmol) in 25 mL ETOH was added all at once and the mixture allowed to stir at room temperature for 2 hrs. The reaction mixture was filtered through a CELITE (D pad and the filtrate evaporated under reduced pressure. The residue was taken up in ET20 (about 200 mL), washed with brine then dried over MGS04. Evaporation of the solvent afforded 2.66g (42%) of 2a as a dark liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 4 2-Bromo-6-methylbenzenamine A mixture of mercuric acetate (100 g, 0.31 mol) and 4-nitrotoluene (500 g, 3.6 mol) is heated at 150 C. for 4 hr. A small amount of precipitate is filtered off and a saturated salt solution is added. The reaction is steam distilled to remove unreacted 4-nitrotoluene (about 350 ml). A gold colored precipitate is filtered off (100 g), crushed to a fine powder and added portionwise to bromine (50 g) in a cold saturated solution of potassium bromide (80 g). This is stirred for 1 hr and chloroform and water is added. A solid by-product is filtered off. The aqueous phase is extracted with chloroform. The combined chloroform extracts are dried and evaporated to afford 90 g of semisolid. Chromatography on silica gel using 80% acetone in toluene gives 46 g of 3-bromo-2-nitrotoluene: nmr (CDCl3) delta 2.5 (s, 3H) and 7.8 (m, 3H). |
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