| Identification | Back Directory | [Name]
5-broMo-1,4-diMethyl-1H-iMidazole | [CAS]
861325-16-8 | [Synonyms]
5-bromo-1,4-dimethylimidazole
5-broMo-1,4-diMethyl-1H-iMidazole
1H-Imidazole, 5-bromo-1,4-dimethyl- | [Molecular Formula]
C5H7BrN2 | [MOL File]
861325-16-8.mol | [Molecular Weight]
175.03 |
| Hazard Information | Back Directory | [Chemical Properties]
5-bromo-1,4-dimethyl-1H-imidazole is a white to off-white crystalline powder that has a melting point of 98-100°C. It is soluble in organic solvents such as ethanol, methanol, and dichloromethane, but insoluble in water. 5-bromo-1,4-dimethyl-1H-imidazole has a molecular weight of 177.05 g/mol and a molecular formula of C6H8BrN2. It has a strong absorption peak at 308 nm in the UV-Vis spectrum, which makes it useful in analytical methods. | [Description]
5-Bromo-1,4-dimethyl-1H-imidazole, also known as BDI, is a heterocyclic organic compound which belongs to the class of imidazoles. BDI is used in analytical methods such as chromatography, electrophoresis and mass spectrometry due to its strong UV-Vis absorption peak at 308 nm. It is also used in the development of sensors and biosensors due to its high sensitivity and selectivity. | [Uses]
5-Bromo-1,4-dimethyl-1H-imidazole is primarily used for scientific research, including organic synthesis, analytical methods, sensors and biosensors, and medicinal chemistry. It has been used as a component in the synthesis of biologically active compounds, including anticancer and antiviral drugs. In addition, it has been used in the development of sensors and biosensors for the detection of various analytes, including glucose, dopamine and hydrogen peroxide. | [Biological Activity]
5-Bromo-1,4-dimethyl-1H-imidazole has anti-inflammatory, antibacterial and antioxidant activities. It has been shown to have antibacterial and antifungal activity against a variety of microorganisms, including Staphylococcus aureus, Escherichia coli and Candida albicans. | [Synthesis]
General procedure for the synthesis of 5-bromo-1,4-dimethyl-1H-imidazole from 4-methyl-5-bromoimidazole and iodomethane: Sodium hydride (60% wt/wt, dispersed in mineral oil, 149 mg, 3.73 mmol, 1.2 eq.) was suspended in anhydrous tetrahydrofuran (10 mL) under nitrogen protection and cooled to 0 °C. To this suspension a solution of 5-bromo-4-methyl-1H-imidazole (500 mg, 3.11 mmol) in tetrahydrofuran (5 mL) was added dropwise. The reaction mixture was stirred at room temperature for 30 min before methyl iodide (661 mg, 4.66 mmol, 1.5 equiv) was added. Stirring was continued for 30 min, after which the reaction mixture was partitioned between ethyl acetate (100 mL) and water (20 mL). The organic phase was separated, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and the resulting crude product was purified by silica gel column chromatography (40 g) using a gradient elution of dichloromethane with methanol (0:100 to 5:95) to afford the target compound 5-bromo-1,4-dimethyl-1H-imidazole as a colorless oil (80 mg, 15% yield).1H NMR (400 MHz, CDCl3): δ = 2.10 (s, 3H) , 3.59 (s, 3H), 7.53 (s, 1H). MS: APCI+ m/z = 174, 176 [MH+]. | [References]
[1] Patent: WO2011/138751, 2011, A2. Location in patent: Page/Page column 95-96 |
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