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What are the chemical properties of 4-Bromo-2-Fluorobenzeneboronic Acid?
4-Bromo-2-fluorophenylboronic acid (4-Bromo-2-Fluorobenzeneboronic Acid) is a crucial reagent in the field of organic synthesis. Its chemical properties are unique and play a key role in many organic reactions.
Looking at its structure, there are bromine atoms, fluorine atoms and boric acid groups attached to the benzene ring. Bromine atoms have good leaving properties and can be replaced by other nucleophilic reagents in nucleophilic substitution reactions. With this property, various chemical bonds such as carbon-carbon bonds and carbon-heteroatomic bonds can be formed. For example, in the Suzuki coupling reaction, bromine atoms can react with other compounds containing boric acid or borate esters to form a series of biphenyl derivatives with different functional groups. This reaction is widely used in drug synthesis, materials science and other fields.
The introduction of fluorine atoms greatly changes the physical and chemical properties of molecules. Fluorine atoms have high electronegativity, which can enhance the polarity of molecules, thereby affecting the solubility, stability and biological activity of compounds. In drug development, fluorine-containing compounds often exhibit unique physiological activities and metabolic stability.
Boric acid groups are also extremely active. Under certain conditions, they can dehydrate to form acid anhydrides, and can also complex with diol compounds to form stable five-membered or six-membered ring structures. This property is often used in organic synthesis to protect o-diol structures or to construct specific cyclic compounds. At the same time, boric acid groups can participate in a variety of metal-catalyzed reactions, providing a rich strategy for organic synthesis.
In addition, the stability of 4-bromo-2-fluorophenylboronic acid needs to be carefully considered under specific conditions. When exposed to strong oxidizing agents, strong bases, and other substances, the corresponding oxidation, hydrolysis, and other reactions may occur in the structure of each group. Therefore, during storage and use, attention should be paid to the influence of environmental factors on its chemical properties, and proper storage is required to maintain its chemical activity. To ensure that it plays its intended role in organic synthesis reactions.
What are the main uses of 4-Bromo-2-Fluorobenzeneboronic Acid?
4-Bromo-2-fluorophenylboronic acid has a wide range of uses and is often used as a key intermediate in the field of organic synthesis.
First, in the reaction of building carbon-carbon bonds, it can participate in the Suzuki coupling reaction. In this reaction, 4-bromo-2-fluorophenylboronic acid and halogenated aromatics or olefins can efficiently generate carbon-carbon bonds under the action of palladium catalyst and base, thereby synthesizing a series of fluorine-bromine-containing biphenyls. Such biphenyl compounds can be used as organic optoelectronic materials in the field of materials science, such as the preparation of organic Light Emitting Diode (OLED) materials. Due to their unique electronic structure and optical properties, they can improve the luminous efficiency and stability of OLEDs.
Second, in the field of pharmaceutical chemistry, 4-bromo-2-fluorophenylboronic acid can be used to synthesize drug molecules with specific biological activities. The introduction of fluorine atoms and bromine atoms can change the lipid solubility, metabolic stability and interaction with drug molecules. With reactions such as Suzuki coupling, it can be connected to the skeleton of drug molecules, providing the possibility for the development of new antibacterial and anticancer drugs. For example, through rational design and synthesis, it is expected to obtain drugs with highly selective inhibitory effects on specific cancer cells.
Third, in terms of material surface modification, 4-bromo-2-fluorophenylboronic acid can be introduced into the material surface as a functional group. Using its reactivity with other compounds, it imparts special properties to the material surface, such as hydrophilicity and biocompatibility. For example, surface modification of biomedical materials can promote cell adhesion and growth, reduce immune rejection, and improve the application effect of materials in vivo.
What is the synthesis method of 4-Bromo-2-Fluorobenzeneboronic Acid?
The synthesis of 4-bromo-2-fluorophenylboronic acid often follows a number of paths. One method involves using 4-bromo-2-fluorobromobenzene as the starting material and reacting it with a strong base such as butyllithium in a low temperature and inert gas atmosphere, such as nitrogen or argon. Butyllithium grabs the hydrogen atom adjacent to the bromine atom to form an extremely reactive organolithium intermediate. This intermediate then reacts with borate esters, such as trimethyl borate or triisopropyl borate. After the reaction, it is hydrolyzed with an acid solution, such as dilute hydrochloric acid or dilute sulfuric acid, to produce 4-bromo-2-fluorophenylboronic acid.
Another method can be used for palladium-catalyzed cross-coupling reaction. 4-Bromo-2-fluorohalobenzene and diphenacol borate are used as raw materials, in the presence of palladium catalysts, such as tetra (triphenylphosphine) palladium (0) or palladium acetate, and ligands, such as tri-tert-butylphosphine or bis (diphenylphosphine) ethane, in suitable organic solvents, such as dioxane and toluene. This reaction uses the action of palladium catalyst to promote the coupling of halobenzene and borate to form the corresponding aryl borate. After alkaline hydrolysis and re-acidification, 4-bromo-2-fluorophenylboronic acid can also be obtained.
Furthermore, 4-bromo-2-fluorophenylboronic acid can be started from 4-bromo-2-fluoroaniline. It is first converted into a diazonium salt through a diazotization reaction, and then reacted with a mixed system of sodium borohydride and boric acid. The diazonium group is replaced by a boric acid group. After a series of post-treatment operations, such as extraction, distillation, crystallization, etc., the pure 4-bromo-2-fluorophenylboronic acid is finally obtained. All synthesis methods have their own advantages and disadvantages. In practical application, it is necessary to comprehensively consider many factors such as the availability of raw materials, cost, reaction conditions and product purity,
4-Bromo-2-Fluorobenzeneboronic Acid need to pay attention to when storing
4-Bromo-2-fluorophenylboronic acid is a commonly used reagent in organic synthesis. When storing, many aspects need to be paid attention to.
First, it is critical to the temperature and humidity requirements of the storage environment. This reagent should be stored in a cool and dry place. Because the temperature is too high, it is easy to cause chemical reactions of the reagent and accelerate its deterioration; and if the humidity is too high, it may cause deliquescence and affect the purity of the reagent. For example, if placed in a high temperature and humid corner, its structure may change, reducing the reactivity, and it is difficult to achieve the desired effect in subsequent organic synthesis reactions.
Second, it is necessary to ensure that it is isolated from air when storing. 4-Bromo-2-fluorophenylboronic acid is easy to react with oxygen, water vapor and other components in the air. It should be stored in a well-sealed container, such as a sealed glass bottle. If the seal is not good, the reagent will come into contact with the air or be oxidized, causing its chemical properties to change, which will affect its application in synthetic reactions.
Third, care should be taken to avoid mixing with other chemicals. This reagent may have adverse reactions with certain chemicals, such as strong oxidizing agents, strong bases, etc. If it is mixed with it, or causes violent chemical reactions, it will not only endanger the quality of the reagent itself, but may also lead to safety accidents.
Fourth, the storage place should be well ventilated. Even if the reagent is sealed and stored, if the storage space is poorly ventilated, once the reagent leaks, the volatile gas cannot be discharged in time, accumulating to a certain extent, or causing safety hazards, such as explosion, poisoning, etc.
Store 4-bromo-2-fluorophenylboronic acid, be sure to pay attention to temperature and humidity, isolate air, avoid co-storage and maintain ventilation, so as to ensure the quality and performance of the reagent, and play its due role in organic synthesis and other related work.
What is the market price of 4-Bromo-2-Fluorobenzeneboronic Acid?
The market price of 4-bromo-2-fluorophenylboronic acid is difficult to be exact, because the price often varies with many factors.
Let's talk about the situation of supply and demand first. If the market demand for this compound increases sharply, such as the need for a large number of new drugs in the pharmaceutical industry, or the new process in the field of electronic materials has urgent demand for it, and the supply is difficult to respond, the price will rise; on the contrary, if the demand is weak, the manufacturer produces too much, and the supply exceeds the demand, the price may decline.
Furthermore, the cost of raw materials is also the key. If the price of starting materials and reagents required for its preparation fluctuates, the price of the product will also be affected. If the price of raw materials such as bromide, fluoride and boron sources increases due to scarcity of resources and production blockages, the cost of 4-bromo-2-fluorophenylboronic acid will increase, thereby driving up the price; if the supply of raw materials is sufficient and the cost is reduced, the price of the product may be reduced.
The production process and technical level also affect its price. Advanced and efficient processes can reduce energy consumption, yield, and impurities, and the cost can be controlled, and the price may be more competitive. If the process is outdated, the production efficiency is low, the loss is large, and the cost is high, the price will be difficult to lower.
The market competition situation cannot be ignored. If there are many manufacturers in the market and the competition is fierce, each manufacturer will compete for a share or adopt a price reduction strategy; conversely, if only a few companies have the capacity to form a certain monopoly, the price may be relatively stable and high.
According to past market estimates, the price of this compound may range from tens to hundreds of yuan per gram. However, this is only an approximate number. The current actual price needs to be consulted in detail with chemical raw material suppliers and chemical product trading platforms to accurately grasp its market price dynamics in real time.