Structure of 1646-53-3
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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. : | 1646-53-3 |
Formula : | C10H13Br |
M.W : | 213.11 |
SMILES Code : | CC1=C(C)C(Br)=C(C)C(C)=C1 |
MDL No. : | MFCD00000070 |
InChI Key : | WJKBPTLQJXKEHC-UHFFFAOYSA-N |
Pubchem ID : | 74240 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
75% | With aluminum (III) chloride; In dichloromethane; at 0 - 25℃; for 8h;Sealed tube; | To a solution of 1-bromo-2,3,5,6-tetramethyl benzene (1.25 g, 8.4 mmol) and acetyl chloride (660 μL, 9.3 mmol) in DCM (50 mL) was cooled in an ice bath. Then AlCl3 (1.4 g, 10.5 mmol) was added portion wise over 10 mins. The resulting mixture was warmed to RT and stirred for 8 h and then poured onto crushed ice (100 g). After the ice had melted, the layers were separated and the aqueous layer was extracted twice with CH2Cl2. The combined organics were washed with brine,dried in MgSO4, filtered and concentrated in vacuo. Purification by flash silica chromatography (eluent = 5% EtOAc in petroleum ether, 30 x 150 mm silica) gave the title compound as a cream solid (1.6 g, 75%), |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With pyridine; potassium permanganate; at 115℃; for 11h; | To a solution of 3-bromo-1,2,4,5-tetramethylbenzene(32.0 g, 150 mmol) in pyridine (260 mL) was added KMnO4 (317g 2.01 mol) in small potions over a period of ca. 8 h at 115 C. After theaddition, the reaction mixture was continuously stirred at the same temperaturefor 3 h. After cooling to room temperature, the reaction mixture was filteredand washed successively with 0.3% aqueous KOH (300 mL x 2) and water. Thecombined filtrate was concentrated under reduced pressure to give while solid,which was dissolved in water (ca. 400 mL) and conc HCl was added to the aqueoussolution and became acidic (pH = 1). The mixture was concentrated under reducedpressure and the concentrate. To the concentrate was added acetone (500 mL),and the mixture was stirred at room temperature and filtered. The filtrate wasconcentrated under reduced pressure to leave white solid, which was dried invacuo at ca. 100 oC for 5 h to give the tetracarboxylic acid as graypowder (22.5 g, 45%); mp >300 oC(decomp.) ; 1H NMR (DMSO-d6,600 MHz) δ 8.43 (s, 1H), 13.82 (br,2H), 13.97 (br, 2H). |
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