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What are the chemical properties of 3-Fluoro-4-Formylbenzeneboronic Acid?
3-Fluoro-4-formylphenylboronic acid, its shape is crystalline, and its color is often nearly white. It has the generality of boric acid and is widely used in the field of organic synthesis.
This substance is acidic, because it contains boric acid groups, it can release protons, and can form salts with bases in suitable media. Its acidity is weaker than that of common inorganic acids, but it shows a specific acid-base behavior in organic boric acids, which is crucial for the control of synthesis reaction conditions.
In terms of reactivity, both formyl groups and boric acid groups are active groups. Formyl groups can be involved in many reactions, such as nucleophilic addition, the carbon of aldehyde groups has positive electricity, which is easy to be attacked by nucleophiles, forms acetals with alcohols, and imines with amines. Boric acid groups are often used in coupling reactions, such as Suzuki-Miyaura coupling, which can form carbon-carbon bonds with halogenated aromatics or olefins under palladium catalysis. This reaction is a powerful tool for constructing complex aromatic structures.
In terms of stability, although it can be stable at room temperature and pressure, it will also change when exposed to high temperatures, strong acids and bases or oxidative reducing agents. High temperatures can cause decomposition, strong acids and bases may change chemical properties, oxidative reducing agents or cause group conversion. Therefore, when storing, it is advisable to avoid these conditions and keep it in a dry and cool place.
In terms of solubility, it has a certain solubility in common organic solvents such as dichloromethane, N, N-dimethylformamide, etc., which is conducive to its dispersion and reaction in organic synthesis reaction systems. In water, boric acid groups can have a certain effect on water and dissolve to a certain extent, but the solubility is related to factors such as temperature and solvent polarity. In short, 3-fluoro-4-formylphenylboronic acid is an extremely useful intermediate in the field of organic synthesis chemistry due to its unique chemical properties.
What are the main uses of 3-Fluoro-4-Formylbenzeneboronic Acid?
3-Fluoro-4-Formylbenzeneboronic Acid (3-Fluoro-4-Formylbenzeneboronic) is an important chemical reagent in the field of organic synthesis, and its use is quite extensive.
First, in the field of medicinal chemistry, it is often used to construct complex molecular structures with biological activity. The design and synthesis of many drug molecules requires the use of such boron-containing compounds with specific substituents. Through a series of organic reactions, such as Suzuki-Miyaura coupling reaction, it can be precisely introduced into the target molecular skeleton to optimize the activity, selectivity and pharmacokinetic properties of drug molecules. For example, in the development of small molecule inhibitors targeting specific disease targets, this compound can be used to couple with other halogenated aromatics to construct key pharmacophore structures, laying the foundation for new drug development.
Second, in the field of materials science, this compound also plays an important role. It can be used to prepare functional organic materials, such as luminescent materials, conductive materials, etc. After rational design and reaction, it is introduced into polymers or other material systems to endow the material with unique optical or electrical properties. For example, in the synthesis of organic electroluminescent Light Emitting Diode (OLED) materials, its reactivity is used to construct a conjugated structure with specific luminescent properties to improve the luminous efficiency and stability of OLED devices.
Third, in the field of total synthesis of natural products, 3-fluoro-4-formylphenylboronic acid is also a commonly used reagent. Natural products often have complex chemical structures and significant biological activities, and precise control of reaction steps and check point selectivity is required during total synthesis. This compound can be used as a key intermediate to participate in multi-step reactions, helping to achieve precise construction of natural product molecules, providing strong support for the research and development and utilization of natural product activities.
What is the synthesis method of 3-Fluoro-4-Formylbenzeneboronic Acid?
The synthesis of 3-fluoro-4-formylphenylboronic acid is a key research in the field of organic synthesis. The following are common synthesis routes:
The starting material is 3-fluoro-4-methylbenzoic acid. The first step is to reduce 3-fluoro-4-methylbenzoic acid, which can be achieved by strong reducing agents such as lithium aluminum hydride (LiAlH). Under low temperature and inert gas protection, slowly add anhydrous ether solution of lithium aluminum hydride to the reaction vessel containing 3-fluoro-4-methylbenzoic acid. After the reaction is complete, 3-fluoro-4-methylbenzyl alcohol can be obtained after acidification.
In the next step, 3-fluoro-4-methylbenzyl alcohol is oxidized to 3-fluoro-4-methylbenzaldehyde. This process can choose a mild oxidizing agent, such as manganese dioxide (MnO ²) or Dess-Martin reagent. Taking manganese dioxide as an example, in a suitable solvent such as dichloromethane, the reflux reaction is heated to gradually convert 3-fluoro-4-methylbenzyl alcohol into 3-fluoro-4-methylbenzaldehyde. After the reaction is completed, the product is purified by means of column chromatography.
In the third step, 3-fluoro-4-methylbenzaldehyde is converted into the target product 3-fluoro-4-formylphenylboronic acid. At this stage, metal-organic reagents such as n-butyllithium (n-BuLi) and borate are often used. At low temperature, 3-fluoro-4-methylbenzaldehyde is treated with n-butyllithium to generate the corresponding lithium reagent. Subsequently, borate esters such as trimethoxyborate (B (OMe) are added. After the reaction is completed, 3-fluoro-4-formylphenylboronic acid can be obtained by hydrolysis. The final product also needs to be carefully purified by recrystallization or column chromatography to achieve high purity.
In addition, there is another synthesis path, and the starting material can be selected as 3-fluoro-4-halobenzaldehyde. 3-fluoro-4-formylphenylboronic acid can also be prepared by reacting with organometallic reagents such as Grignard reagents and then reacting with borate esters. During synthesis, precise control of reaction conditions, such as temperature, reaction time, and reagent dosage, have a significant impact on the yield and purity of the product. The purification operation after each step of the reaction should not be underestimated, which is related to the quality of the final product.
3-Fluoro-4-Formylbenzeneboronic Acid in storage and transportation
3-Fluoro-4-formylphenylboronic acid is a commonly used reagent in organic synthesis. When storing and transporting, pay attention to the following things:
First, when storing, it should be placed in a dry, cool and well-ventilated place. This substance is afraid of moisture and is prone to deterioration due to moisture, which affects its chemical activity. Therefore, it should be stored in a dryer, or a desiccant should be added around the storage container to maintain a dry environment.
Second, because it is more sensitive to temperature, high temperature will promote its decomposition or accelerate deterioration, and the storage temperature should usually be controlled between -20 ° C and 0 ° C. If conditions permit, low-temperature frozen storage is more appropriate, which can effectively prolong its shelf life.
Third, during transportation, be sure to pack tightly to prevent leakage. If this reagent leaks, it will not only be wasted, but also may cause pollution to the environment, and even cause safety problems due to chemical reactions. Packaging materials should be selected that can resist vibration and collision, such as using foam and other buffer materials to wrap.
Fourth, 3-fluoro-4-formylphenylboronic acid will react with water, oxygen, etc., so when storing and transporting, try to isolate water and air. Nitrogen-filled packaging can be used, that is, filling the packaging container with nitrogen to create an oxygen-free environment and slow down its deterioration.
Fifth, storage and transportation should be away from fire, heat and strong oxidants. This reagent has certain chemical activity, and may cause combustion or even explosion in case of fire and heat sources. Contact with strong oxidants may also cause violent chemical reactions, endangering safety.
What is the market price of 3-Fluoro-4-Formylbenzeneboronic Acid?
I look at your question, but I am inquiring about the market price of 3-fluoro-4-formylphenylboronic acid. However, the price of this chemical often changes for many reasons, and it is difficult to say exactly.
First, the difference between the manufacturer and the quality has a great impact on the price. If the factory has excellent craftsmanship and strict quality control, the quality of the products produced is high, and the price may be high; while the craftsmanship is slightly inferior and the quality control is not strict, the price may be lower.
Second, the state of market supply and demand is also the key. If there are many people who want it, the supply is small, and the price will rise; on the contrary, if the supply exceeds the demand, the price will fall easily.
Third, the purchase quantity also affects the price. The purchase quantity is small, or according to the retail price, it is relatively high; if you buy in large quantities, the manufacturer may give a certain discount due to small profits but quick turnover, and the price is slightly lower.
Fourth, the prices of different sales channels are different. Purchased from regular large suppliers, or due to comprehensive protection, the price may be higher; and from small merchants or special channels, the price may be different.
According to the market situation in the past, the price of such chemicals fluctuated from a few yuan to tens of yuan per gram. However, this is only a rough estimate. For the exact price today, you need to consult the chemical product supplier in detail, or check it on the relevant chemical product trading platform, in order to obtain an accurate price.