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What is the chemical structure of 4-Fluoro-2-Formylbenzeneboronic Acid?
4-Fluoro-2-formylphenylboronic acid, this is an important compound in organic chemistry. Looking at its name, its structural characteristics can be known. "Phenylboronic acid" is based on the benzene ring and is connected with a boric acid group (-B (OH) -2). "4-fluoro" indicates that there is a fluorine atom at position 4 of the benzene ring; "2-formyl" is shown at position 2 of the benzene ring, connected with a formyl group (-CHO). The chemical structure of
is as follows: with the benzene ring as the central skeleton, at position 2 of the benzene ring, it is connected to the formyl group through a carbon-carbon bond, and the carbon atom and the oxygen atom in the formyl group are connected by a double bond, forming a > C = O structure; at position 4 of the benzene ring, it is connected to the fluorine atom by a carbon-fluorine bond; and at position 1 of the benzene ring, it is connected to the boric acid group. The boron atom in the boric acid group is connected to two hydroxyl groups (-OH), forming a B (OH) -2 structure.
This structure endows the compound with unique chemical properties and has important uses in the field of organic synthesis. It is often used as a key intermediate, participating in many organic reactions, and assisting in the construction of more complex organic molecular structures.
What are the main uses of 4-Fluoro-2-Formylbenzeneboronic Acid?
4-Fluoro-2-formylphenylboronic acid has a wide range of uses and is often used as a key intermediate in the field of organic synthesis.
First, in the construction of carbon-carbon bond reactions, such as Suzuki-Miyaura coupling reaction, 4-fluoro-2-formylphenylboronic acid can efficiently form biaryl or alkenylated products with halogenated aromatics or alkenes under the action of palladium catalysts and bases. This reaction is of great significance in the fields of medicinal chemistry and materials science, and can prepare organic molecules with specific structures and functions. By this method, many biologically active drug molecules can be synthesized, providing key raw materials for pharmaceutical research and development.
Second, it can also play an important role in the construction of carbon-heteroatom bond reactions. It can react with nucleophiles containing nitrogen, oxygen, sulfur and other heteroatoms to form compounds with different functional groups. This has contributed a lot to the synthesis of organic materials with special properties, such as photoelectric materials. It can be used to prepare organic materials that can efficiently emit light or conduct electricity, and promote the development of materials science.
Third, because it contains both fluorine atoms and formyl and boric acid groups, it can provide a multi-component modification check point when designing novel organic molecular structures. Chemists can perform derivatization reactions on it according to specific needs to obtain compounds with specific spatial structures and electronic properties. This provides the possibility for the design of unique catalysts or host molecules in cutting-edge research fields such as supramolecular chemistry and asymmetric catalysis, which helps to explore and innovate in related fields.
What is the synthesis method of 4-Fluoro-2-Formylbenzeneboronic Acid?
The synthesis of 4-fluoro-2-formylphenylboronic acid is an important topic in organic synthetic chemistry. The common methods for its synthesis have several ends.
First, it can be started by the corresponding halogenated aromatic hydrocarbon. First take 4-fluoro-2-halogenated benzaldehyde, in which the halogen atom can be bromine or iodine. This halogen is reacted with an organolithium reagent, such as n-butyllithium, under harsh conditions of low temperature and no water and no oxygen. The n-butyllithium reacts with the halogen atom to form the corresponding aryl lithium intermediate. This intermediate is extremely active and then reacts with borates, such as trimethoxyborates. After the hydrolysis step, 4-fluoro-2-formylphenylboronic acid can be obtained. In this process, low temperature anhydrous and anaerobic conditions are the key, because the aryl lithium intermediate is extremely unstable, and it is easy to decompose in contact with water and oxygen, causing the reaction to fail.
Second, it can also be achieved by gradually introducing the required groups from compounds with some substituents on the benzene ring as raw materials. For example, the benzene ring is first formylated, a formyl group is introduced, then a fluorine atom is introduced, and finally a boric acid group is introduced through a specific reaction. This approach requires precise control of the reaction conditions and selectivity of each step, because different substituents on the benzene ring have a significant impact on the positioning effect of subsequent reactions. Each step of the reaction requires careful consideration of factors such as the ratio of reactants, reaction temperature, reaction time, and the catalyst used to ensure that the reaction proceeds in the desired direction and minimize the occurrence of side reactions.
Third, the coupling reaction catalyzed by transition metals is also a feasible method. Using aromatic halide and borate esters containing suitable substituents as raw materials, carbon-boron bonds are constructed under the action of transition metal catalysts such as palladium and nickel. Such reactions usually require the assistance of ligands to enhance the activity and selectivity of the catalyst. Selecting suitable ligands and optimizing the conditions such as bases and solvents in the reaction system are crucial to improve the yield and selectivity of the reaction.
In short, the synthesis of 4-fluoro-2-formylphenylboronic acid requires weighing the advantages and disadvantages of each method according to the specific situation, carefully designing the reaction route, and strictly controlling the reaction conditions to obtain the ideal synthesis effect.
What are the physical properties of 4-Fluoro-2-Formylbenzeneboronic Acid?
4-Fluoro-2-formylphenylboronic acid, which is a white to off-white solid. Its melting point is usually between 130 and 135 ° C. At this temperature, the substance changes from solid to liquid, exhibiting its phase change characteristics.
In terms of solubility, it is slightly soluble in water. Water is a common solvent in which many organic compounds have different solubility. Although the boric acid group in this compound has a certain hydrophilicity due to its own structure, the presence of fluorine atoms, benzene rings and formyl groups makes the overall hydrophilicity limited, so it is only slightly soluble in water. However, it is soluble in common organic solvents such as dichloromethane, N, N-dimethylformamide, etc. In dichloromethane, good dissolution can be achieved by virtue of the interaction between chlorine atoms and some groups of compounds; in N, N-dimethylformamide, dissolution can also be achieved by virtue of the interaction between its polar environment and compounds.
The compound has certain chemical stability, but the boric acid group makes it more sensitive to humidity. In humid environments, boric acid groups easily react with water, which in turn affects their chemical structure and properties. In addition, both formyl groups and boric acid groups are reactive and can participate in a variety of organic synthesis reactions, such as acetalization with alcohols under specific conditions, condensation with amines, etc., and are widely used in the field of organic synthesis.
What are the precautions for 4-Fluoro-2-Formylbenzeneboronic Acid in storage and transportation?
For 4-fluoro-2-formylphenylboronic acid, many things need to be paid attention to during storage and transportation. This is a chemical substance, which is active in nature, so when storing, the drying of the environment is the first priority. Because it is quite sensitive to moisture, if the environment is humid, it is easy to react with water, causing it to deteriorate and its efficacy is greatly reduced.
Furthermore, temperature is also a key factor. It should be stored in a cool place to avoid hot topics. Under high temperature, this substance may decompose or even cause safety risks. Generally speaking, the temperature should be maintained at 2-8 degrees Celsius, and this temperature range can ensure the stability of its chemical properties.
During transportation, the packaging must be solid and reliable. Special packaging materials are required to prevent damage and leakage due to vibration and collision. And the packaging should have good sealing, isolating air and moisture. At the same time, the temperature should also be controlled during transportation to ensure that the temperature is appropriate.
In addition, 4-fluoro-2-formylphenylboronic acid may be toxic and irritating. Storage and transportation personnel must be equipped with protective equipment, such as gloves, masks, goggles, etc., to prevent contact or inhalation, endangering their own health. When handling, it should also be handled with care and handled with caution.
In addition, compliance with relevant regulations and standards is also a top priority. No matter whether it is the setting of the storage site or the planning of the transportation process, it is necessary to comply with the regulations of the state and the industry, and must not act recklessly to ensure the safety and order of the entire process.