Structure of 2-Bromo-3-formylthiophene
CAS No.: 1860-99-7
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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. : | 1860-99-7 |
Formula : | C5H3BrOS |
M.W : | 191.05 |
SMILES Code : | O=CC1=C(Br)SC=C1 |
MDL No. : | MFCD09025880 |
InChI Key : | MMEGVQIGIBCTHI-UHFFFAOYSA-N |
Pubchem ID : | 12245921 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 8 |
Num. arom. heavy atoms | 5 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 37.41 |
TPSA ? Topological Polar Surface Area: Calculated from |
45.31 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.6 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.09 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.32 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.19 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.38 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.12 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.74 |
Solubility | 0.35 mg/ml ; 0.00183 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.67 |
Solubility | 0.407 mg/ml ; 0.00213 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.47 |
Solubility | 0.647 mg/ml ; 0.00339 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 |
-5.98 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 |
1.0 |
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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.21 |
* 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 |
---|---|---|
78.8% | With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 60 - 70℃; Inert atmosphere | In a 250 ml two-necked flask, 11.9 g of 2-bromo-3- (bromomethyl) thiophene (256 g mol- 1, 11.9 g, 46 mmol)Pump without water treatment.Under N2 protection, 20.8 g of IBX (280 g mol-1, 20.8 g, 74 mmol, 1.6 equiv)Add 130ml anhydrous DMSO, 60-70°C oil bath for 3-4 hours.After treatment: add 20ml of deionized water to quench the reaction. The mixture was extracted with dichloromethane, washed with a large amount of methylene chloride, and precipitated as a white solid. The filtrate was collected by suction filtration, dried and concentrated by column chromatography.Eluent petroleum ether / ethyl acetate 40: 1 (V: V). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With Dess-Martin periodane In tetrahydrofuran at 0℃; for 3 h; | To a solution of (2-bromothiophen-3-yl)methanol (5 g, 26.3 mmol) in THF (60 mL) at 0 °C was added Dess-Martin periodinane (13.4 g, 31.6 mmol) in portions. After stirring at 0 °C for 3 h, water and Na2S03 were added. The mixture was extracted with DCM, and the combined organic layers were washed with brine and dried over anhydrous Na2S04. After filtration and concentration, the crude product was purified by column chromatography to give the title compound (4.1 g, 83percent). |
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