Structure of 700-36-7
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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. : | 700-36-7 |
Formula : | C6H3BrFNO2 |
M.W : | 220.00 |
SMILES Code : | BrC1=C(C=CC(=C1)F)[N+](=O)[O-] |
MDL No. : | MFCD00792441 |
Boiling Point : | No data available |
InChI Key : | VGYVBEJDXIPSDL-UHFFFAOYSA-N |
Pubchem ID : | 2756993 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 42.92 |
TPSA ? Topological Polar Surface Area: Calculated from |
45.82 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.64 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.4 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.92 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.06 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.81 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.96 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.05 |
Solubility | 0.194 mg/ml ; 0.000884 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.0 |
Solubility | 0.218 mg/ml ; 0.000991 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.92 |
Solubility | 0.266 mg/ml ; 0.00121 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 |
-5.94 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) |
1.86 |
* 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 |
---|---|---|
Sodium hydride (60percent in mineral oil; 0.985 g) is suspended in N,N-dimehylforamamide (20 mL), and to this suspension was added dropwise a solution of tert-butyl methyl malonic acid ester (4.29 g) in N,N-dimethylformamide (5 mL) under ice-cooling. After completion of the foam generation, a solution of 2-bromo-4-fluoro-1-nitrobenzene (2.71 g) in N,N-dimethylformamide (5 mL) was dropwise added thereto at the same temperature, and the mixture was stirred at 60°C for 3 hours. The reaction mixture was concentrated, neutralized with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4 to 5) to give the title compound (7.54 g) as an oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With sodium hydroxide; In water; at 95 - 105℃; | (3) Hydrolysis reaction, 700 mL of 15percent aqueous sodium hydroxide solution was added to the reaction flask, and the reaction temperature was controlled at 95 to 105 °C.160.4 g of the above nitro compound was added in portions, and the reaction was continued for a while, and the GC was followed until the reaction was completed.After a little cold, acidification, ice water water analysis, suction filtration, to obtain the target 150 g,The content is more than 98percent, and the yield is 98percent. |
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