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What are the chemical properties of 5-Bromo-6-fluoropyridine-3-amine?
5-Bromo-6-fluoropyridine-3-amine, this is an organic compound. Its chemical properties are unique and of great research value.
From the structural point of view, the compound contains halogen elements such as bromine and fluorine, and there are amino groups connected to the pyridine ring. Halogen elements endow it with special reactivity. Bromine atoms are large in size and have high electron cloud density. It can affect the molecular charge distribution through induction and conjugation effects, which changes the density of electron clouds in the adjacent and para-position of the pyridine ring, and is prone to nucleophilic substitution reactions. Fluorine atoms are extremely electronegative, which not only affects molecular polarity, but also enhances molecular stability. Due to the high carbon-fluorine bond energy, this compound is more stable under certain reaction conditions. The
amino group is nucleophilic and can participate in a variety of reactions. Under acidic conditions, the amino group is easily protonated, causing the whole molecule to assume a cationic state, changing its solubility and reactivity. In the field of organic synthesis, it is often used as a nucleophilic reagent to replace with halogenated hydrocarbons, acyl halides, etc., to form nitrogen-containing derivatives. The
pyridine ring is also a key structural part and has aromatic properties. Its electron cloud distribution is unique and it presents weak alkalinity. Since the electronegativity of the nitrogen atom of the pyridine ring is higher than that of the carbon atom, the electron cloud on the ring is biased towards the nitrogen atom, so that the electron cloud density of the carbon atom of the pyridine ring is relatively reduced, the electrophilic substitution reaction activity is lower than that of the benzene ring, and the reaction check point is mostly in the β-position (i.e. 3-position and 5-position). The compound has an amino group at the 3-position, a bromine atom at the 5-position, and a fluorine atom at the 6-position, which further affects the reactivity and selectivity of the pyridine ring.
In addition, the physical properties of 5-bromo-6-fluoropyridine-3-amine, such as melting point, boiling point, solubility, etc., are also affected by the interaction of these functional groups with the pyridine ring. Its solubility may vary in different solvents due to the mutual check and balance of amino hydrophilicity with halogen atoms and pyridine ring hydrophobicity. It may have a certain solubility in organic solvents such as dichloromethane, N, N-dimethylformamide, but its solubility in water may be limited.
In summary, 5-bromo-6-fluoropyridine-3-amine has a unique structure, which combines the characteristics of halogen elements, amino groups and pyridine rings, and has active and complex chemical properties. It may have wide application prospects in organic synthesis, medicinal chemistry and other fields.
What are the common synthetic methods of 5-Bromo-6-fluoropyridine-3-amine?
5-Bromo-6-fluoropyridine-3-amine, an important intermediate in organic synthesis. Its common synthesis methods are as follows:
- ** With halopyridine as the starting material **:
- Select an appropriate halopyridine, such as a pyridine derivative containing bromine or fluorine, and introduce an amino group through a nucleophilic substitution reaction. Taking bromopyridine as an example, it can react with ammonia or ammonia derivatives under suitable conditions. In an autoclave, using potassium carbonate as a base and an appropriate amount of phase transfer catalyst to assist, halopyridine is mixed with ammonia water, heated to an appropriate temperature (such as 80-120 ° C), and the target product can be obtained after several reactions. This is to use the nucleophilicity of ammonia to replace the halogen atom to form a carbon-nitrogen bond.
-If the starting material is fluoropyridine, the reactivity of fluorine atoms can be exploited. Under the catalysis of copper salt or palladium salt, react with organic amine source. For example, using cuprous iodide as a catalyst, the ligand is 1,10-phenanthroline, and the base is cesium carbonate, in an organic solvent (such as N, N-dimethylformamide), the reaction is heated, and the fluorine atom is replaced by an amino group to obtain 5-bromo-6-fluoropyridine-3-amine. < Br > - ** Constructed by pyridine ring **:
- With suitable nitrogen, bromine and fluorine raw materials, the pyridine ring is constructed by cyclization reaction, and then the target product is obtained. For example, using β-carbonyl compound, ammonia source, halogenated hydrocarbons containing bromine and fluorine as raw materials, the pyridine ring is constructed through multi-step reaction. First, the β-carbonyl compound is condensed with ammonia to obtain an enamide intermediate, and then nucleophilic substitution occurs with halogenated hydrocarbons. After intramolecular cyclization, aromatization and other steps, the pyridine ring is synthesized to obtain 5-bromo-6-fluoropyridine-3-amine. This process requires fine control of the reaction conditions, and the reaction conditions of each step are different, such as the condensation reaction temperature, the acid-base environment of the cyclization reaction, etc.
- In addition, heterocyclic synthesis reagents, such as 2-amino-3-bromo-4-fluorobenzoic acid, can be used to react with suitable reagents to construct pyridine rings. Under the action of dehydrating agents (such as phosphorus oxychloride), the reaction is heated, and intramolecular dehydration and cyclization occur to form pyridine rings. After subsequent treatment, 5-bromo-6-fluoropyridine-3-amine is obtained. < Br >
Synthesis of 5-bromo-6-fluoropyridine-3-amine requires a reasonable selection of synthesis methods based on factors such as raw material availability, cost, and difficulty of reaction conditions, in order to achieve high efficiency and economy.
In what areas is 5-Bromo-6-fluoropyridine-3-amine applied?
5-Bromo-6-fluoropyridine-3-amine, which is used in many fields. In the field of medicinal chemistry, it is often a key intermediate for the creation of new drugs. Due to its specific chemical structure, it can be linked to other active groups by organic synthesis to construct compounds with unique pharmacological activities. For example, when developing antibacterial drugs, this may be used as a starting material, or new drugs with high inhibitory effect on specific pathogens can be derived, providing new ways to fight infectious diseases.
In the field of materials science, 5-bromo-6-fluoropyridine-3-amine also shows potential uses. It can participate in the preparation of organic materials with special photoelectric properties. After rational molecular design and synthesis strategies, its introduction into polymer is expected to endow the material with unique optical and electrical properties, such as excellent fluorescence properties or charge transport capabilities. It may play an important role in the manufacturing of organic Light Emitting Diodes (OLEDs), solar cells and other devices, helping to improve device performance and efficiency.
Furthermore, in the field of pesticide chemistry, the compound also has application prospects. Based on its structural modification and optimization, new and efficient pesticides may be developed. Its unique structural characteristics may make it highly selective and bioactive to certain pests or weeds, while reducing its impact on the environment, providing beneficial contributions to sustainable agricultural development. In conclusion, the unique chemical structure of 5-bromo-6-fluoropyridine-3-amine has important application value in many fields such as medicine, materials, and pesticides, providing a key foundation for technological innovation and development in various fields.
What is the market outlook for 5-Bromo-6-fluoropyridine-3-amine?
5-Bromo-6-fluoropyridine-3-amine, this product has a promising market prospect today, and there are considerable challenges.
Looking at its application field, it is a key intermediate in pharmaceutical chemistry. Due to its unique chemical structure, it can participate in the construction of various drug molecules. In recent years, the demand for characteristic structure intermediates in pharmaceutical research and development has been increasing. Pyridine amines containing fluorine and bromine have attracted much attention in the exploration of antibacterial, anti-inflammatory and anti-tumor drugs. Therefore, in this field, 5-bromo-6-fluoropyridine-3-amine has a bright future. If pharmaceutical innovation continues to advance, its demand is expected to rise.
In the field of materials science, organic optoelectronic materials are developing rapidly. Such halogen-containing and nitrogen-containing heterocyclic compounds may have potential uses in the research and development of organic Light Emitting Diodes (OLEDs) and organic photovoltaic cell materials due to their unique electronic properties. With the frontier exploration of materials science, if its advantages in the preparation of new materials can be confirmed, the market demand will meet new growth points.
However, its market also has challenges. The complexity of the synthesis process is one of them. To obtain high purity 5-bromo-6-fluoropyridine-3-amine, fine synthesis steps and conditions need to be controlled, and the synthesis cost may remain high, limiting large-scale application. And the market competition is fierce, and similar intermediates or substitutes continue to emerge. If the production company does not have technical and cost advantages, it is difficult to take the lead in the market. Stringent environmental protection requirements are also influential factors. The treatment of waste in the synthesis process requires compliance, which increases production costs and management difficulties.
Overall, 5-bromo-6-fluoropyridine-3-amine has a good market prospect due to the application potential. However, factors such as process, competition and environmental protection make its development path need to move forward cautiously. Only by breaking through difficulties can we enjoy market dividends.
What are the precautions in the preparation of 5-Bromo-6-fluoropyridine-3-amine?
When preparing 5-bromo-6-fluoropyridine-3-amine, many things need to be paid attention to.
The selection of starting materials is extremely critical. The selected raw materials should have high purity. If there are too many impurities, it will not only reduce the yield of the product, but also cause frequent side reactions. For example, if the raw materials contain impurities with similar structures, they may compete with the main reactants for the reaction check point during the reaction process, and finally produce impure products.
The control of reaction conditions should not be underestimated. In terms of temperature, it needs to be strictly maintained within a specific range. If the temperature of this reaction is too high, it may initiate excessive halogenation or other unnecessary decomposition reactions; if the temperature is too low, the reaction rate will be slow, and the reaction may even be difficult to start. Take a similar reaction as an example. If the temperature deviates by 5 ° C, the yield of the product may fluctuate by 10% - 20%. The pressure also needs to be precisely adjusted according to the reaction characteristics. Some reactions can only proceed smoothly under specific pressures. Improper pressure may cause the reaction direction to shift.
The solvent used has a significant impact on the reaction. The solvent should not only have good solubility to the reactants, but also be compatible with the reaction system. An inappropriate solvent may prevent the reactants from being fully contacted, reduce the reaction efficiency, or cause side reactions with the reactants and products. For example, polar solvents may not be suitable for some non-polar reaction systems.
Monitoring during the reaction process is essential. Real-time monitoring of the reaction process by means of thin-layer chromatography (TLC), high-performance liquid chromatography (HPLC), etc., can provide timely insight into whether the reaction is advancing as expected. Once abnormal reactions are found, such as reaction stagnation or the generation of a large number of by-products, the reaction conditions can be adjusted in time.
Post-processing steps are also critical. The separation and purification of the product requires careful operation. Appropriate separation methods, such as extraction and column chromatography, are used to effectively remove impurities. During extraction, if the selected extractant is not appropriate, the product and impurities may not be separated efficiently. In column chromatography, the selection of stationary and mobile phases is wrong, which will make it difficult to effectively separate the product and impurities, thus affecting the purity of the product.
Operators are also required to follow strict safety procedures. Some of the reagents involved in this reaction may be toxic, corrosive, or flammable. Reagents such as brominated reagents are usually highly corrosive and toxic, and must be operated in a well-ventilated environment, wearing protective equipment, and avoiding contact with the skin and respiratory tract to prevent danger.