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2-Bromo-1H-imidazole is an organic compound with the chemical formula C3H3BrN2, CAS 16681-56-4, and a relative molecular weight of 137.97 g/mol. Usually in the form of white or slightly yellow solid crystals, it is a solid that is in the form of crystals or crystalline powders at room temperature. It is insoluble in water, but soluble in many organic solvents, such as ethanol, methanol, Dimethyl sulfoxide, etc. Its solubility may vary under acidic and alkaline conditions. The melting point is approximately between 107 and 112 ° C, depending on the crystal morphology and purity. The molecule contains a bromine atom and an imidazole ring. The nitrogen atom in the center of its Molecular formula forms a Conjugated system with the carbon atom on the imidazole ring, making the molecule more stable. Intermediates commonly used in drug synthesis. It can be used to synthesize various biologically active compounds. It can be used as an intermediate for pesticides and fungicides. To form stable coordination compounds with metal ions as ligands. Its derivatives can be used for the synthesis of photovoltaic materials. Photovoltaic materials are an important component of optoelectronic devices such as solar cells, and have broad application prospects.
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Chemical Formula |
C3H3BrN2 |
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Exact Mass |
146 |
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Molecular Weight |
147 |
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m/z |
146 (100.0%), 148 (97.3%), 147 (3.2%), 149 (3.2%) |
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Elemental Analysis |
C, 24.52; H, 2.06; Br, 54.37; N, 19.06 |
2-Bromo-1H-imidazole is an organic compound with a unique chemical structure, containing bromine atoms and imidazole rings in its molecule. As an important heterocyclic structure, imidazole ring exhibits unique properties and application value in many fields. The introduction of bromine atoms endows it with some special reactivity and functions.
Application in organic synthesis
As a synthetic intermediate
2-Bromo-1H-imidazole is an important intermediate for the synthesis of many organic compounds. When constructing complex organic molecules, various functional groups can be introduced through the substitution reaction of the bromine atom in 2-Bromo-1H-imidazole, gradually synthesizing the target molecule. For example, in the synthesis of some biologically active heterocyclic compounds, 2-Bromo-1H-imidazole can be used as a starting material, and through a series of reaction steps, other functional groups can be attached to the imidazole ring to ultimately obtain compounds with specific pharmacological activities.
Participation in coupling reactions
Coupling reaction is an important method for constructing carbon carbon bonds and carbon heteroatom bonds in organic synthesis. 2-Bromo-1H-imidazole can participate in various coupling reactions, such as palladium catalyzed coupling reactions. Under the action of palladium catalyst, 2-Bromo-1H-imidazole can undergo coupling reaction with arylboronic acid or alkenylboronic acid to generate biaromatic or alkenylimidazole compounds containing imidazole rings. These products have important application value in fields such as drug synthesis and materials science. For example, through palladium catalyzed coupling reactions, 2-Bromo-1H-imidazole can be coupled with arylboronic acids containing different substituents to synthesize a series of imidazole aromatic compounds with potential anti-tumor activity.
Used for building multi ring systems
By utilizing the chemical reactivity of 2-Bromo-1H-imidazole, a polycyclic heterocyclic system can be constructed. For example, 2-Bromo-1H-imidazole can be converted into polycyclic compounds containing imidazole rings through intramolecular cyclization reactions. These polycyclic compounds often have unique chemical properties and biological activities, and have broad application prospects in drug development and materials science. In addition, 2-Bromo-1H-imidazole can also react with other heterocyclic compounds to form multi ring heterocyclic systems with complex structures, providing rich ideas and methods for organic synthesis.
Application in the field of medicine
2-Bromo-1H-imidazole and its derivatives play an important role in the development of antibacterial drugs. Many studies have shown that compounds containing imidazole rings have certain antibacterial activity. By modifying the structure of 2-Bromo-1H-imidazole and introducing different substituents, a series of compounds with stronger antibacterial activity can be synthesized. These compounds can act on important targets such as bacterial cell walls, cell membranes, or nucleic acids, inhibiting bacterial growth and reproduction. For example, some imidazole compounds containing 2-Bromo-1H-imidazole structures have significant inhibitory effects on common pathogens such as Staphylococcus aureus and Escherichia coli, providing potential candidate compounds for the development of new antibacterial drugs.
Research and development of anti-tumor drugs
In the development of anti-tumor drugs, 2-Bromo-1H-imidazole has also shown certain potential. The imidazole ring structure appears in many anti-tumor drugs, and it can exert anti-tumor effects by interfering with the metabolic processes of tumor cells, inhibiting tumor cell proliferation, or inducing tumor cell apoptosis. Researchers have synthesized a series of derivatives with anti-tumor activity by optimizing the structure of 2-Bromo-1H-imidazole. These derivatives have shown certain anti-tumor effects in in vitro cell experiments and animal experiments, providing new directions for the development of novel anti-tumor drugs. For example, certain compounds containing 2-Bromo-1H-imidazole can inhibit tumor cell angiogenesis, thereby cutting off the tumor's nutritional supply and achieving the goal of inhibiting tumor growth.
2-Bromo-1H-imidazole and its derivatives also have certain applications in the development of antiviral drugs. Some viruses require specific enzymes or proteins to replicate and spread during the process of infecting host cells. Compounds containing imidazole rings can bind to these viral enzymes or proteins, inhibit their activity, and thus block the replication cycle of the virus. Through structural modification of 2-Bromo-1H-imidazole, compounds with antiviral activity can be synthesized to treat some viral infectious diseases, such as influenza, AIDS, etc. For example, studies have shown that certain derivatives of 2-Bromo-1H-imidazole have a certain inhibitory effect on the neuraminidase of influenza virus, which can alleviate influenza symptoms and shorten the course of the disease.
Application in Materials Science
Coordination Chemistry
Due to the lone pair electrons of the nitrogen atom in 2-Bromo-1H-imide, it can form complexes with metal ions. These complexes have important application value in materials science. For example, the complex formed between 2-Bromo-1H-imidazole and transition metal ions can serve as a catalyst for organic synthesis reactions. These complex catalysts have high selectivity and activity, and can catalyze reactions that are difficult to achieve with traditional catalysts. In addition, 2-Bromo-1H-imide based complexes can also be used to prepare functional materials such as luminescent materials, magnetic materials, etc. By adjusting the structure and composition of the complex, material properties can be controlled to meet different application requirements.
Polymer Materials
2-Bromo-1H-imidazole can participate in the synthesis and modification of polymer materials. For example, it can be used as a monomer to copolymerize with other polymer compounds, introducing imidazole ring structures to improve the properties of polymer materials. Polymer materials containing 2-Bromo-1H-imide structure may have better thermal stability, chemical stability, and mechanical properties. In addition, 2-Bromo-1H-imidazole can also be used as a crosslinking agent to form crosslinked structures between polymer chains, further improving the properties of polymer materials. For example, in some rubber products, introducing 2-Bromo-1H-imide as a crosslinking agent can enhance the strength and wear resistance of the rubber.
Optical Materials
2-Bromo-1H-imidazole and its derivatives also have certain applications in the field of optical materials. Some compounds containing imidazole rings have unique optical properties, such as fluorescence, phosphorescence, etc. By modifying the structure of 2-Bromo-1H-imidazole, materials with specific optical properties can be synthesized for the preparation of optical sensors, fluorescent probes, etc. For example, some 2-Bromo-1H-iminazole derivatives can emit strong fluorescence under specific wavelength light excitation, and the fluorescence intensity is related to the concentration of certain substances in the surrounding environment. Therefore, they can be used as fluorescent probes for detecting metal ions, biomolecules, etc.
Application in the field of pesticides
Research and development of insecticides
2-Bromo-1H-imidazole and its derivatives have certain potential in the development of insecticides. Many pests have specific physiological metabolic processes and targets, and compounds containing imidazole rings can interfere with these processes to achieve insecticidal effects. For example, some derivatives of 2-Bromo-1H-imidazole can inhibit acetylcholinesterase activity in pests, causing neurological dysfunction and ultimately leading to death. By optimizing the structure of 2-Bromo-1H-imidazole, its insecticidal activity and selectivity can be improved, reducing its impact on non target organisms and developing more environmentally friendly and efficient insecticides.
Research and development of fungicides
In terms of fungicides, 2-Bromo-1H-imidazole and its derivatives can also play an important role. The cell wall synthesis, cell membrane function, and nucleic acid metabolism of plant pathogens are potential targets for sterilization. Compounds containing imidazole rings can act on these targets, inhibiting the growth and reproduction of pathogens. For example, certain derivatives of 2-Bromo-1H-imidazole can interfere with the synthesis of pathogenic bacterial cell walls, leading to the rupture and death of pathogenic bacterial cells. Researchers can synthesize compounds with broad-spectrum bactericidal activity by structurally modifying 2-Bromo-1H-imidazole, which can be used to prevent and control various plant diseases.
Research and development of herbicides
Although there is relatively little research on the use of 2-Bromo-1H-imidazole in herbicides, the imidazole ring structure has been applied in other herbicides. Through in-depth research and structural modification of 2-Bromo-1H-imidazole, it is possible to develop herbicides with novel mechanisms of action. These herbicides can interfere with the growth and development process of weeds, such as inhibiting photosynthesis and cell division, thereby achieving the goal of weed control. Compared with traditional herbicides, herbicides based on 2-Bromo-1H-imidazole may have higher selectivity and lower toxicity, making them more environmentally friendly.
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