Structure of 1003709-39-4
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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. : | 1003709-39-4 |
Formula : | C8H6BrFO2 |
M.W : | 233.03 |
SMILES Code : | O=C(O)C1=CC(C)=C(F)C=C1Br |
MDL No. : | MFCD09263434 |
InChI Key : | UVSGTNJGIMPLAM-UHFFFAOYSA-N |
Pubchem ID : | 45073546 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 46.03 |
TPSA ? Topological Polar Surface Area: Calculated from |
37.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.61 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.6 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.02 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.09 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.77 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.62 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.23 |
Solubility | 0.138 mg/ml ; 0.000593 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.03 |
Solubility | 0.216 mg/ml ; 0.000928 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.3 |
Solubility | 0.118 mg/ml ; 0.000505 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) |
No |
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 |
-5.88 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 |
0.56 |
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) |
1.56 |
* 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 |
---|---|---|
74% | With N-Bromosuccinimide; dibenzoyl peroxide; In acetonitrile; for 4.0h;Reflux; | A mixture of 2-bromo-4-fluoro-5-methyl-benzoic acid (0.5 g, 2.14 mmol), N-bromosuccinimide (381 mg, 2.15 mmol) and benzoyl peroxide (10 mg, 0.04 mmol) in CH3CN (10 mL) was heated at reflux for 4 h. The reaction mixture was cooled to 0 C and 5% aqueous Na2S203 was added. The CH3CN was evaporated and the residue was extracted with EtOAc (3 x 100 mL). The combined organic phases were dried (Na2S04), filtered, and evaporated. The residue was purified by chromatography (silica gel, 2-20% EtOAc/hexane) to give 2-bromo-5-bromomethyl- 4-fluoro-benzoic acid (500 mg, 74%). MS calcd. for C8H6Br2F02 [(M-H) ] 309, obsd. 308.6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With sodium chlorite; potassium dihydrogenphosphate; aminosulfonic acid; In 1,4-dioxane; water; at 20.0℃; | A mixture of 2-bromo-4-fluoro-5-methyl-benzaldehyde (available from 3B Scientific Corporation, 1840 Industrial Drive, Suite 160, LibertyviUe, IL 60048, USA; 1.0 g, 4.61 mmol), sulfamic acid (2.68 g, 27.65 mmol), sodium chlorite (539 mg, 6 mmol) and KH2P04 (7.52 g, 55.3 mmol) in 50% aqueous dioxane (96 mL) was stirred at room temperature overnight. The reaction mixture was concentrated, and water (20 mL) was added. The resulting mixture was extracted with EtOAc (3 x 250 mL). The combined organic layers were dried (Na2S04), filtered, and evaporated to give 2-bromo-4-fluoro-5-methyl-benzoic acid (1.0 g, 93%) as an off-white solid. MS calcd. for C8H7BrF02 [(M-H) ] 231, obsd. 231.0. |
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