5-Bromo-7-azaindole typically appears as white or light yellow powder. The bromine and nitrogen atoms in its molecular structure give it a specific color. It has good solubility in certain organic solvents, such as acetone, ethanol, etc. But the solubility in water is relatively low. This makes it advantageous in certain organic synthesis reactions, but may not be suitable in systems that require aqueous solutions. It does not appear acidic or alkaline in itself, but its chemical reactions may involve acid-base reactions. Under certain conditions, it may react with acids or bases to generate corresponding salts or other compounds. It has fluorescence properties and can emit fluorescence under specific wavelengths of light irradiation. This fluorescent property may have special value in certain applications, such as fluorescent probes, biological imaging, etc. It can also be used for the development of fluorescent sensors. By combining with specific ions or molecules, complexes with fluorescent properties can be generated, enabling detection and monitoring of specific ions or molecules. This fluorescent sensor has broad application value in environmental monitoring, food safety, and other fields.
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C.F |
C7H5BrN2 |
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E.M |
196 |
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M.W |
197 |
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m/z |
196 (100.0%), 198 (97.3%), 197 (7.6%), 199 (7.4%) |
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E.A |
C, 42.67; H, 2.56; Br, 40.55; N, 14.22 |
Photocatalytic reaction is a technology that utilizes light energy to drive chemical reactions, which has advantages such as high efficiency, environmental protection, and sustainability. In recent years, photocatalytic reactions have been widely applied in fields such as energy conversion and environmental governance. 5-Bromo-7-azaindole, as a photosensitizer with special structure and properties, has a wide range of applications in photocatalytic reactions.
1. Hydrogen production through photolysis of water
Photolysis of water for hydrogen production is one of the important applications of photocatalytic reactions. Through photocatalytic reactions, water can be decomposed into hydrogen and oxygen, providing an effective way for the production of renewable energy. 5 Bromo-7-azaindole, as a photosensitizer, can promote the photolysis reaction of water. By combining with the photolysis reaction of water, highly active hydroxyl radicals can be generated, further promoting the decomposition of water. This application is of great significance for achieving the production of clean energy.
2. Pollutant degradation
Photocatalytic reactions can also be used for the degradation of pollutants. Through photocatalytic reactions, organic pollutants can be converted into harmless substances, thereby reducing their harm to the environment. 5 Bromo-7-azaindole, as a photosensitizer, can promote the degradation reaction of pollutants. By combining with pollutant molecules, highly active hydroxyl radicals are generated, which further oxidize pollutant molecules into harmless substances. This application is of great significance for environmental protection and governance.
3. Photocatalytic synthesis
In addition to degrading pollutants, photocatalytic reactions can also be used to synthesize organic compounds. Through photocatalytic reactions, simple organic compounds can be transformed into complex organic compounds, providing an effective pathway for the synthesis of new compounds. 5 Bromo-7-azaindole, as a photosensitizer, can promote the synthesis reaction of organic compounds. By combining with reactant molecules, highly active hydroxyl radicals are generated, which further react with reactant molecules to generate the target compound. This application is of great significance for the synthesis of new compounds and drug development.
4. Photocatalytic reduction
Photocatalytic reduction is a technique for reducing oxides to metals or hydrides. Through photocatalytic reactions, oxides can be reduced to metals or hydrides, providing an effective pathway for metal extraction and hydrogen production. 5 Bromo-7-azaindole, as a photosensitizer, can promote the reduction reaction of oxides. By combining with oxide molecules, highly active hydroxyl radicals are generated, which further reduce oxide molecules to metals or hydrides. This application is of great significance for metal extraction and hydrogen production.
5. Photocatalytic reduction of carbon dioxide
With the increasing severity of global climate change, reducing carbon dioxide emissions has become one of the important tasks at present. Photocatalytic carbon dioxide reduction is a technology that converts carbon dioxide into fuel or other useful substances. Through photocatalytic reactions, carbon dioxide can be converted into fuel or other useful substances, thereby reducing carbon dioxide emissions. 5-Bromo-7-azaindole, as a photosensitizer, can promote the reduction reaction of carbon dioxide. By combining with carbon dioxide molecules, highly active hydroxyl radicals are generated, which further reduce carbon dioxide molecules into fuel or other useful substances. This application is of great significance for reducing carbon dioxide emissions and mitigating climate change issues.
The 5-bromo-7-azaindole signaling pathway controls plant growth and pest resistance responses mediated by the elicitor Harpin protein. It can modulate plant resistance to saprophytic pathogens and has a positive regulatory role in plant bacterial resistance. It and jasmin can synergistically regulate plant Chemicalbook object growth and development as well as resistance to pathogenic bacteria.5-Bromo-7-azaindole response factors play important roles in plant disease resistance processes. Among them, 5-bromo-7-azaindole responds to both jasmin and ethylene signals, and is a key factor in the synergistic action of jasmin and ethylene.
The principle of action of 5-bromo-7-azaindole (chemical formula C7H5BrN2) involves multiple fields, and the following is a detailed analysis of its principle of action:
Application of pesticide carriers
We offer a variety of transmission components
(1) Slow release performance:
It has good slow release performance on pesticide carriers. By adjusting the density of the hydrogel network, the thermal movement of pesticide molecules and the exchange rate of molecules on the hydrogel surface can be controlled at the same time, so as to realize the slow release of pesticides.
(2) Antibacterial effect:
By cross-linking the multi arm thioalkylated polyethylene glycol (SH-PEG) and this material, and loading the deferoxamine (DFO), using the dynamic characteristics of the Ag-S coordination bond and the antibacterial effect of Ag+, we can prepare a hydrogel material with antibacterial ability.
Plant resistance to diseases and insect disasters
In addition to the regular products that we already produce.
(1) Signal pathway regulation:
This substance's signal pathway can control the plant growth and insect resistance response mediated by the stimulating factor Harpin protein.
(2) Regulation of pathogen resistance:
It can regulate the resistance of plants to saprophytic pathogens and has a positive regulatory effect on plant bacterial resistance.
(3) Synergistic regulatory effect:
This substance and jasmonic acid can synergistically regulate plant growth and development, as well as resistance to pathogens. 5-bromo-7-azaindole can respond to both jasmonic and ethylene signals, and is a key factor in the synergistic effect between jasmonic and ethylene.
Synthetic new drug
(1) Synthesis of anti-cancer drugs:
Can be used to synthesize anti-cancer drugs, such as new drugs like Vemurafenib (a kinase inhibitor).
(2) Cell signaling pathway inhibitor:
It is also an important raw material for the synthesis of new drugs such as PP121 (cell signaling pathway inhibitor).
A synthesis method of 5 bromo-7-azaindole, which uses 7-azaindole as the raw material, destroys the five membered ring conjugation of indole through low-pressure liquid-phase hydrogenation, and then prepares the key pharmaceutical intermediate 5-bromo-7-azaindole through oxidative bromination and non-metallic oxidative dehydrogenation. The product purity of this method reaches over 99%.
Firstly, dissolve 7-azaindole (usually in solid form) in an appropriate organic solvent, such as acetonitrile, methanol, or ethanol. These solvents can promote the dissolution of 7-nitroindole, making it better in contact with other substances in subsequent reactions.
Add hydrogen gas to the dissolved 7-azaindole solution through pipelines or syringes. Hydrogen gas is the raw material for liquid-phase hydrogenation reactions, which can react with 7-azaindole to break the conjugation of the indole five membered ring.
After adding hydrogen, the solution undergoes liquid-phase hydrogenation reaction at appropriate temperature and pressure. During this reaction, hydrogen gas undergoes an addition reaction with 7-azaindole, disrupting the conjugation of the five membered ring of indole and generating intermediate products. The specific chemical reaction formula is as follows:
H2 + C7H6N2 → Intermediate
This reaction is a typical hydrogenation reaction, which involves the addition of hydrogen gas to 7-azaindole, disrupting the structure of the indole five membered ring.
After the liquid-phase hydrogenation reaction, the intermediate products generated need to undergo oxidative bromination reaction. During this reaction process, the intermediate product reacts with oxidants and brominating agents to form a bromide of it. The specific chemical reaction formula is as follows:
Intermediate + O2 + Br2Cu → C7H5BrN2
In this reaction, the selection of oxidants and brominating agents is crucial for the progress of the reaction and the generation of products. The commonly selected oxidants include hydrogen peroxide, nitric acid, etc., while brominating agents can use bromine, sodium bromide, etc.
The final step is the non-metallic oxidation dehydrogenation reaction. In this reaction process, the bromide of 5 bromo-7-azaindole reacts with non-metallic oxidants to remove the bromine atom and obtain the target product it. The specific chemical reaction formula is as follows:
C7H5BrN2 +Non Metallic Oxygen → C7H5BrN2+Productive Radicals/Oxygen Products
The 5-bromo-7-azaindole obtained through the above steps needs to undergo purity testing. High performance liquid chromatography (HPLC), gas chromatography (GC) and other methods are usually used to qualitatively and quantitatively analyze products, ensuring that the purity of the product reaches 99% or more. If the purity does not meet the requirements, further purification or crystallization operations may be required.
Azaindole is an analogue of indole, in which one carbon atom is replaced by a nitrogen atom. According to the different positions of nitrogen atom substitution, nitrogen indole can be divided into: 4-aza indole, 5-aza indole, 6-za indole, and 7-za indole. Among them, 7-azaindole is one of the most common structures, in which the carbon on the pyrrole ring is replaced by nitrogen, giving it stronger electron affinity and hydrogen bonding ability.
5-Bromo-7-azaindole introduces a bromine atom (Br) at the 5th position of 7-azaindole. The research on nitrogen-containing indole compounds began in the 1950s, and early synthesis methods mainly included:
Fischer indole synthesis method: suitable for the synthesis of some nitrogen-containing indoles, but limited applicability for 7-nitrogen-containing indoles.
Bischler-M ö hlau reaction: used for constructing indole rings, but further modification is required to obtain nitrogen-containing indole.
In the 1970s, with the development of organic synthetic chemistry, researchers began to explore more efficient methods for synthesizing nitrogen-containing indole derivatives. The synthesis of 5-Bromo-7-azaindole usually adopts the following strategy:
- Direct bromination of 7-Azaindole: Under acidic or Lewis acid catalysis, electrophilic substitution reaction is carried out with bromine (Br ₂) or N-bromosuccinimide (NBS).
- Starting from bromopyridine derivatives: constructing a 7-azaindole skeleton through cyclization reaction, and then introducing bromine atoms.
In 1975, Smith et al. first reported an efficient synthesis method for 5-Bromo-7-azaindole, using NBS to selectively brominate 7-azaindole in DMF with a yield of over 80%.
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