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What are the chemical properties of 4-Chloro-2-Fluorobenzeneboronic Acid?
4-Chloro-2-fluorophenylboronic acid is an important reagent in organic synthesis. Its chemical properties are unique and have many wonders.
In terms of acidity, phenylboronic acids are usually weakly acidic. The boric acid group of 4-chloro-2-fluorophenylboronic acid (-B (OH) ²) can give protons and exhibit acidic properties. However, compared with common inorganic acids, its acidity is weaker. Due to the special electronic structure of the outer layer of boron atoms, the electron cloud of oxygen atoms in the hydroxyl groups is attracted by boron atoms, resulting in a change in the polarity of hydrogen-oxygen bonds, making it easier to dissociate hydrogen ions. However, due to the limited degree of attraction of boron atoms to electrons, the acidity is weak.
In the nucleophilic substitution reaction, the compound also has excellent performance. Both the chlorine atom and the fluorine atom on the benzene ring have certain activity. The chlorine atom is slightly more electronegative than carbon, and the lone pair electron of the chlorine atom has a p-π conjugation effect with the benzene ring, which makes the carbon positive ion intermediate connected to the chlorine atom relatively stable and prone to nucleophilic substitution. Although the fluorine atom is extremely electronegative and has a large carbon-fluorine bond energy, it is not easy to be replaced under normal circumstances. However, when it interacts with strong nucleophilic reagents under specific conditions, it can also participate in the reaction. And the chlorine and fluorine atoms on the benzene ring are affected by the boric acid group,
In addition, the boric acid group of 4-chloro-2-fluorophenylboronic acid can participate in a variety of coupling reactions, such as the Suzuki-Miyaura coupling reaction. In such reactions, boric acid groups cross-couple with organic halides or pseudo-halides under the action of palladium catalysts and bases, forming carbon-carbon bonds to construct complex organic molecular structures. This reaction has mild conditions and high selectivity, and is widely used in drug synthesis, materials science and other fields.
At the same time, the physical properties of the compound are also closely related to its chemical properties. Its appearance is mostly white to light yellow solid powder, which has certain solubility in organic solvents, such as common tetrahydrofuran, dichloromethane, etc. This solubility facilitates its uniform dispersion in organic synthesis reaction systems and participation in various reactions.
In conclusion, 4-chloro-2-fluorophenylboronic acid plays a key role in the stage of organic synthesis due to its unique chemical properties, providing a powerful tool for the development of many fields.
What are the main uses of 4-Chloro-2-Fluorobenzeneboronic Acid?
4-Chloro-2-fluorophenylboronic acid has a wide range of uses. It is a key intermediate in the field of pharmaceutical synthesis. The creation of many new drugs relies on its participation in reactions to build specific molecular structures, which in turn endows drugs with unique pharmacological activities. For example, when developing targeted drugs for specific diseases, 4-chloro-2-fluorophenylboronic acid can react with other functional groups through its boron group to precisely connect the required pharmacodynamic groups and improve the efficacy of drugs.
In the field of materials science, it also has important functions. When preparing organic optoelectronic materials, it can be introduced into organic molecular systems as a structural modification unit. Due to the special electronic structure of boron atoms, the electron cloud distribution and energy level structure of materials can be effectively adjusted, thereby improving the optical and electrical properties of materials, such as improving the fluorescence efficiency and charge transport ability of materials, which are used in the manufacture of organic Light Emitting Diodes (OLEDs), organic solar cells and other devices.
In the field of chemical synthesis, it is often used as a coupling reaction reagent. For example, in the Suzuki-Miyaura coupling reaction, 4-chloro-2-fluorophenylboronic acid can be coupled with substrates such as halogenated aromatics or olefins under the action of suitable catalysts and bases to form carbon-carbon bonds, and to achieve efficient synthesis of complex organic compounds. The reaction conditions are relatively mild and highly selective, providing a convenient and practical synthesis method for organic synthesis chemists to prepare organic compounds with specific structures and functions, which play an important role in the production of fine chemical products.
What is the synthesis method of 4-Chloro-2-Fluorobenzeneboronic Acid?
The synthesis of 4-chloro-2-fluorophenylboronic acid can follow the following steps. First take 4-chloro-2-fluorobromobenzene as the starting material, which is the basis of the reaction. In a dry reaction vessel, fill an appropriate amount of anhydrous ether or tetrahydrofuran as a solvent to create a suitable reaction environment.
The reaction system is cooled to a low temperature, about -78 ° C, which can precisely regulate the reaction process. Slowly add n-butyl lithium, n-butyl lithium has very high activity, and the reaction is initiated when it comes into contact with the substrate, so that the bromine atom in 4-chloro-2-fluorobromobenzene is replaced by a lithium atom to form a 4-chloro-2-fluorophenyl lithium intermediate.
Wait for the reaction to be stable, continue to maintain the low temperature state, and slowly add trimethyl borate. Trimethyl borate undergoes a nucleophilic substitution reaction with 4-chloro-2-fluorophenyl lithium intermediate, and the lithium atom is replaced by a borate ester group. After a period of reaction, 4-chloro-2-fluorophenyl borate intermediate is formed in the system.
After the reaction is completed, the system is heated to room temperature to promote the further completion of the reaction. Subsequently, an appropriate amount of dilute hydrochloric acid or dilute sulfuric acid is added for hydrolysis. During the hydrolysis process, trimethyl 4-chloro-2-fluorophenylborate is converted into the target product 4-chloro-2-fluorophenylboronic acid.
After the hydrolysis is completed, the product is separated by extraction method. Multiple extractions are made with an organic solvent such as ethyl acetate or dichloromethane, the organic phases are combined, and then dried with anhydrous sodium sulfate to remove the moisture in it. Finally, the product is purified by reduced pressure distillation or column chromatography to remove impurities, and pure 4-chloro-2-fluorophenylboronic acid can be obtained.
Although the steps of this synthesis method are complex, the reaction conditions of each step are clear, and proper operation can lead to products with higher yield and purity.
4-Chloro-2-Fluorobenzeneboronic Acid during storage and transportation
For 4-chloro-2-fluorophenylboronic acid, there are many matters to be paid attention to during storage and transportation.
First word storage. This product should be stored in a cool, dry and well-ventilated place. Because of its certain chemical activity, if placed in a high temperature or humid place, it may cause chemical reactions and cause quality damage. For example, high temperature can promote its decomposition, humid environment or make it interact with water vapor to change the chemical structure. Therefore, choosing a suitable storage environment is the key to ensuring its stability.
Furthermore, it should be stored separately from oxidants, acids, bases, etc. The chemical properties of 4-chloro-2-fluorophenylboronic acid make it easy to react violently when it comes into contact with these substances, or cause dangerous conditions such as combustion and explosion. Be sure to strictly follow the principle of classified storage to prevent accidents.
As for transportation, make sure that the packaging is intact. The transportation container must be able to withstand a certain amount of external force to avoid the package breaking due to bumps and collisions, and the leakage of items. Once leaked, it not only pollutes the environment, but also poses a threat to the safety of transporters.
During transportation, it should also be protected from high temperature and fire sources. Because it is more sensitive to heat, it may encounter open flames, hot topics, or the risk of combustion and explosion. Transport vehicles should also be kept clean and free of other residues that may react with them.
In addition, transport personnel should be familiar with the characteristics of this product and emergency treatment methods. If there are emergencies on the way, such as leaks, etc., they can respond quickly and correctly to reduce the harm. In short, when storing and transporting 4-chloro-2-fluorophenylboronic acid, every step needs to be carefully operated and strictly followed to ensure safety.
What is the market price of 4-Chloro-2-Fluorobenzeneboronic Acid?
The market price of 4-chloro-2-fluorophenylboronic acid is difficult to determine due to many factors. Looking at the price of chemical products in the past, it was often determined by raw materials, supply and demand, technology and market competition.
First of all, raw materials, the preparation of this product requires specific halogenated aromatics and boron sources. If the output of raw materials changes, or in case of natural disasters or geopolitical supply shortages, the price will rise; on the contrary, if raw materials are abundant, the price is expected to drop.
The relationship between supply and demand is also key. If many industries, such as pharmaceutical and electronic materials research and development, have a surge in demand for them, and the supply is difficult to respond for a while, the price will rise; if the demand is flat and the manufacturer's inventory is overstocked, the price will fall for promotional sales.
The preparation process also has a great impact. The advent of new and efficient processes can reduce costs and increase output, and the price will also change due to it. The market competition situation should not be underestimated. Many manufacturers compete fiercely to survive in order to gain share or reduce prices. If the market is oligopolized, the pricing power of manufacturers will increase, and the price may rise steadily.
To sum up, although it is difficult to determine the exact market price, the price per gram may fluctuate between tens of yuan and hundreds of yuan according to the past state of the chemical market. To know the accurate price in real time, it is also necessary to carefully review the chemical product trading platform and relevant market information.