Structure of 29578-83-4
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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. : | 29578-83-4 |
Formula : | C8H9BrO |
M.W : | 201.06 |
SMILES Code : | CC1=CC(OC)=CC(Br)=C1 |
MDL No. : | MFCD08061916 |
InChI Key : | AOEVRCZZWJWKPG-UHFFFAOYSA-N |
Pubchem ID : | 10679554 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 45.6 |
TPSA ? Topological Polar Surface Area: Calculated from |
9.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.54 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.95 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.77 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.88 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.96 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.82 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.32 |
Solubility | 0.0956 mg/ml ; 0.000475 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.81 |
Solubility | 0.314 mg/ml ; 0.00156 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.77 |
Solubility | 0.0342 mg/ml ; 0.00017 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 |
-5.43 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 |
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) |
1.42 |
* 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 |
---|---|---|
With sodium hydroxide; dimethyl sulfate; In water; | EXAMPLE 9 A mixture of <strong>[74204-00-5]5-bromo-3-hydroxytoluene</strong> (93 g, 0.5 m) and sodium hydroxide (21 g, 0.5 m) in water (200 ml) is stirred at 10°, treated with dimethyl sulfate (63 g, 0.5 m) over 1 hour, refluxed for 2 hours and cooled. The mixture is diluted with water and extracted with ether. The ether extract is washed, dried with sodium sulfate and concentrated in vacuo to give 5-bromo-3-methoxytoluene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2 mmol <strong>[74137-36-3]3,5-dibromoanisole</strong> were dissolved in 10 ml THF and cooled to -78°C. 2.4 mmol of n- BuLi were added dropwise and stirring was continued for 15 min. 3 mmol of methyl iodide were added and the mixture was allowed to slowly warm to ca. -200C over a period of ca. 2 h. IM HCl and dichloromethane were added and the phases were separated. 1.65 mmol of crude 3-bromo-5- methylanisole were taken to the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With potassium carbonate; In acetone; at 40℃; for 16.0h; | To a mixture of <strong>[74204-00-5]3-bromo-5-methyl-phenol</strong> (185 g; 0.940 mol) and K2CO3 (437 g, 3.17 mol) in acetone (2 L) is added MeI (424 g, 2.99 mol). The mixture is stirred at 40° C. for 16 h. The mixture is cooled to ambient temperature, filtered, and concentrated under reduced pressure. After filtration, the mixture is purified by flash silica gel chromatography to afford 1-Bromo-3-methoxy-5-methyl-benzene, D-4-1 (189 g, quant. yield) as a light yellow oil. |
85.8% | With potassium carbonate; In acetonitrile; for 3.0h;Reflux; | C. Preparation of 3-methyl-5-methoxybromobenzene In a three-necked flask, 3-methyl 5-bromophenol (10.0 g, 53.5 mmol), potassium carbonate (22.2 g, 160.4 mol) andIodomethane (7.6 g, 53.5 mol) was dissolved in acetone (50 mL) and refluxed for 3 h. After the reaction is complete, add 30 mL of water, methylene chloride(50mL × 3) extraction, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated under reduced pressure to give 3-methyl-5-methoxybromobenzene white.Crystals 9.2 g, yield 85.8percent |
52% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 24.0h; | [0297] To the mixture of compound 29-1 (300 g, 1.6 mol) and K2CO3 (665 g, 4.8 mol) in DMF (2000 mL) was added MeI (250 g, 1.8 mol) dropwised at room temperature. The mixture was stirred overnight. TLC showed the reaction is completed. The reaction was quenched by H2O and extracted with EtOAc. The organic layer was dried, filtered, evaporated under reduced pressure to give the crude product which was purified by chromatography on silica gel to give compound 29-2 (165 g, 52percent yield). |
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