Structure of 5469-19-2
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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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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 5469-19-2 |
Formula : | C9H11Br |
M.W : | 199.09 |
SMILES Code : | CC1=C(C)C=C(C)C(Br)=C1 |
MDL No. : | MFCD00000072 |
InChI Key : | SCZXFZRJDVZMJI-UHFFFAOYSA-N |
Pubchem ID : | 79610 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.33 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 49.04 |
TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.63 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.64 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.37 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.98 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.9 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.5 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.81 |
Solubility | 0.0307 mg/ml ; 0.000154 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.33 |
Solubility | 0.0935 mg/ml ; 0.000469 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.42 |
Solubility | 0.00766 mg/ml ; 0.0000385 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
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) |
Yes |
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 |
-4.93 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 |
2.0 |
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<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.39 |
* 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 |
---|---|---|
97.3% | With sulfuric acid; dihydrogen peroxide; iodine; iron(II) sulfate; sodium bromide; In dichloromethane; water; at 0℃; | Weigh three toluene 0.1mol,0.15 mol of sodium bromide,30% sulfuric acid solution 0.08mol in three-necked flask,Then, 50 g of dichloromethane was added as a solvent,Add catalyst 0.8g ferrous sulfate,0.05g of iodine,The three-necked flask placed 0 low temperature tank, mixing, fully dissolved.A solution of 10% aqueous hydrogen peroxide (H2O, 20.08 mol) was added dropwise at 0 C over 3-5 hours,And incubated for 6 hours.The reaction is over, standing stratification,The organic phase was washed with 100 mL of water, repeated three times, and then the aqueous solution was extracted with 30 mL of dichloromethane, repeated three times. The organic phase solutions were combined,The methylene chloride was recovered under reduced pressure to give a crude solid product, which was recrystallized from twice the mass of gasoline to give white crystals,Is trimethylbenzene, about 19.4 g, yield 97.3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium permanganate; water; sodium carbonate; for 60h;Reflux; | Preparation 1 d: 2-tert-Butyl 5-methyl 6-hromo-2,3-dibydro-1H-isoiiidole-2,5-dicarboxylateStep A: S-Brornobenzene-1,2,4-tricarboxylic acidBromotrimethyl benzene (40.7 g, 205 mmol) was added to a mixture of water (3.25 L), potassium permanganate (232 g, 1.468 mol) and sodium carbonate (28.5 g, 206 mmol). The mixture was stirred at reflux for 60 h. Ethanol (820 mE) was added dropwise, and theresultant mixture was filtered hot through celite, then allowed to cool to ambient temperature. The filtrate was acidified with concentrated aqueous HCI, and the organic solvent was removed in vacuo, The solid product was isolated by filtration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | With sulfuric acid; nitric acid; for 5h;Cooling with ice; | <strong>[5469-19-2]2-bromo-1,4,5-trimethylbenzene</strong> (10g, 50mmol) was dissolved in concentrated sulfuric acid (20mL) inThen in the ice water bath,Concentrated nitric acid (3.5 g, 1.1 eq) was slowly added.After 5 hours of reaction,The reaction mixture was poured into ice-water, filtered,The yellow solid was collected, washed with water, and then column chromatographed (petroleum ether / ethyl acetate = 50/1) to afford the product (2.3 g, 19% yield) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Bromo-2,4,5-trimethyl-benzene (1) (10.00 g, 50.23 mmol) was added into a two-necked flask. The reaction vessel was degassed and refilled with nitrogen three times and then 120 mL of distilled THF was added. The flask was cooled to -78 C and n-butyllithium (25.00 mL, 2.40 M in hexane) was added dropwise. After stirring at -78 C for 2 h, 7.80 mL of dimethyl formamide was added dropwise. The mixture was allowed to react for another 6 h at -78 C and was then warmed to room temperature.Saturated NH4C1 aqueous solution was added to quench the reaction. The mixture was extracted with dichloromethane (DCM). The organic layer was separated, washed with deionized water and brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was evaporated under reduced pressure and the crude product was purified by silica gel column chromatography using hexanelDCM (5/1, v/v) as eluent. 6.30 g of 2,4,5-trimethyl-benzenaldehyde (2) was obtained as white powder in 85.0% yield. 2 (2.00 g, 13.50 mmol) and zinc dust (2.65 g, 40.50 mmol) were added into a two-necked flask with a reflux condenser. The reaction vessel was degassed and refilled with nitrogen three times and then 100 mL of THF was added into the flask. The mixture was cooled to -78 C and TiC14 (2.23 mL, 20.25 mmol) was added dropwise by syringe. The mixture was slowly warmed to room temperature. After stifling for 1 h, the mixture was refluxed for another 24 h. The reaction was quenched with 4% aqueous HC1 solution and filtered. The mixture was extracted with DCM. The organic layer was collected, washed with deionized water and brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was evaporated under reduced pressure and the crude product was purified by silica gel column chromatography using hexane/DCM (5/1, v/v) as eluent. 1.43 g of DPE-TM was obtained as white powder in 80.3% yield. |
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