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What is the chemical structure of O-Trifluorobenzeneboronic Acid?
The chemical structure of O-Trifluorobenzeneboronic Acid consists of a benzene ring as the backbone. Above the benzene ring, a boric acid group (-B (OH) -2) is connected to the ortho-position (O-position). In this boric acid group, the boron atom (B) is connected to two hydroxyl groups (-OH) in a planar triangular spatial configuration. The boron atom has electron-deficient properties, which makes the boric acid group tend to accept electron pairs, and often shows unique activity in chemical reactions.
At the same time, there are three fluorine atoms (-F) connected to the rest of the benzene ring. Fluorine atoms have strong electronegativity, which has a great influence on the electron cloud distribution of the benzene ring. Due to the significant electron-absorbing induction effect (-I effect) of fluorine atoms, the electron cloud density of the benzene ring decreases, especially the adjacent and para-potential electron cloud densities. The change in the distribution of this electron cloud results in a significant change in the chemical activity of the benzene ring compared with the ordinary benzene ring.
The existence of fluorine atoms not only affects the electron cloud density of the benzene ring, but also affects the spatial structure of the molecule. Although the radius of fluorine atoms is small, due to its large electronegativity, the interaction with surrounding atoms cannot be ignored, which in turn affects the physical and chemical properties of the molecule as a whole. Such a chemical structure endows O-trifluorophenylboronic acid with unique application value in many fields such as organic synthesis and medicinal chemistry, and can participate in a variety of chemical reactions, such as Suzuki-Miyaura coupling reaction, providing an effective way to construct complex organic molecular structures.
What are the main uses of O-Trifluorobenzeneboronic Acid?
O-Trifluorobenzeneboronic acid is widely used in the field of organic synthesis. It is often used as an arylating reagent and participates in the Suzuki-Miyaura reaction. In this reaction, O-trifluorophenylboronic acid can be used with halogenated aromatics or alkenyl halides, palladium catalysts and bases to form carbon-carbon bonds. It is widely used in pharmaceutical chemistry, materials science, etc., and can synthesize many biologically active compounds and functional materials.
In drug development, with the help of Suzuki-Miyaura reaction, O-trifluorophenylboronic acid can be used to synthesize complex drug molecules, providing a key method for the creation of new drugs. For example, in the development of anti-tumor drugs, specific structural fragments are constructed through this reaction to improve drug activity and selectivity.
In the field of materials science, it is used to participate in the synthesis of materials with special photoelectric properties. For example, the preparation of organic Light Emitting Diode (OLED) materials can adjust the electronic structure and optical properties of the materials, so that OLEDs exhibit better luminous efficiency and color purity.
In addition, O-trifluorophenylboronic acid can also be used to synthesize liquid crystal materials, improve the arrangement and performance of liquid crystal molecules, and improve the display effect of liquid crystal displays. At the same time, it is also used in the synthesis of new sensor materials. By reacting with specific molecules, a sensor with high selectivity recognition ability for specific substances can be constructed to achieve accurate detection of target substances.
What are the physical properties of O-Trifluorobenzeneboronic Acid?
O-Trifluorobenzeneboronic Acid is a key reagent in organic synthesis. Its physical properties are particularly important, and it is related to the performance and application of this reagent in various reactions.
Looking at its properties, under normal circumstances, O-trifluorophenylboronic acid is mostly white to white solid powder. This form is easy to weigh and store, and it is easy to disperse in the reaction system, which is conducive to the smooth development of the reaction.
When it comes to the melting point, its melting point range is about 90-95 ° C. As an important physical constant of the substance, the melting point can help chemists determine the purity of the reagent. If the melting point is consistent with the established range, it can be proved that the purity is good; if there is any deviation, it may suggest that it contains impurities and needs to be further purified.
In terms of solubility, O-trifluorophenylboronic acid is slightly soluble in common organic solvents, such as ether, dichloromethane, etc. In water, its solubility is also limited. This solubility characteristic determines its applicability in different reaction systems. In the organic phase reaction, it can effectively participate in the reaction because of its soluble part of the organic solvent; but in the aqueous phase-based reaction, the degree of solubility needs to be considered when using it, or it needs to be better dispersed and participated in the reaction by means of phase transfer catalysts.
And its stability, under normal storage conditions, in a dry and cool place, O-trifluorophenylboronic acid can be stably stored. However, it is more sensitive to humidity, and its structure and activity are changed when exposed to water or high humidity environments, or reactions such as hydrolysis occur. Therefore, it is necessary to ensure that the environment is dry when storing, and seal it in time after use to prevent failure.
These physical properties are factors that chemists must consider carefully when applying O-trifluorophenylboronic acid in many fields such as organic synthesis and drug development. Only in this way can the reaction be carried out efficiently and accurately to achieve the expected synthesis goal.
What is the preparation method of O-Trifluorobenzeneboronic Acid?
The method for preparing o-trifluorophenylboronic acid (O - Trifluorobenzeneboronic Acid) follows the following steps.
First, o-trifluorobrobenzene is used as the starting material. In a dry reaction bottle, nitrogen is filled to remove air. Many reagents in the reaction are sensitive to air. An appropriate amount of anhydrous tetrahydrofuran is added as a solvent, which can effectively dissolve the reactants and provide a suitable environment for the reaction. Then the reaction bottle is cooled to a low temperature, such as -78 ° C, and n-butyl lithium is slowly added dropwise. N-butyl lithium and o-trifluorobrobenzene will undergo lithium halogen exchange reaction to form o-trifluorophenyl lithium intermediate. This intermediate is highly active and requires careful handling to maintain a low temperature environment to prevent side reactions.
Second, when the lithium-halogen exchange reaction is completed, a borate ester, such as trimethyl borate, is slowly added to the reaction system. In this step, lithium-trifluorophenyl and trimethyl borate undergo nucleophilic substitution to generate the corresponding borate ester derivative. After the reaction is completed, let the system slowly warm up to room temperature to further complete the reaction.
Third, after the reaction is completed, the reaction mixture is post-treated. Add an appropriate amount of dilute hydrochloric acid solution for hydrolysis, and hydrolyze the borate ester into the target product o-trifluorophenylboronic acid. After the hydrolysis is completed, an organic solvent such as ether or ethyl acetate is used for extraction to separate the organic phase. The organic phase is dried with anhydrous sodium sulfate to remove the moisture in it. Finally, the organic solvent is removed by reduced pressure distillation, and the product is purified by column chromatography or recrystallization to obtain pure o-trifluorophenylboronic acid.
Another method is to use o-trifluoroaniline as the starting material. First, o-trifluoroaniline is converted into diazo salt by diazotization reaction, and then reacted with boric acid reagent to prepare o-trifluorophenylboronic acid. However, this method is relatively complicated, and attention should be paid to the control of the conditions of the diazotization reaction to prevent danger.
O-Trifluorobenzeneboronic Acid to pay attention to when storing and transporting
O-Trifluorobenzeneboronic Acid is a commonly used reagent in organic synthesis. When storing and transporting, many key matters need to be paid attention to.
When storing, the first environmental conditions. Because of its certain chemical activity, it should be stored in a dry and cool place. Humid environment can easily cause its hydrolysis, thus damaging the quality and activity. This is because boron atoms easily react with water molecules to change the structure of the compound. Therefore, the humidity of the warehouse should be controlled at a low level, for example, the relative humidity should not exceed 60%.
Temperature is also crucial. Generally speaking, it should be stored in a low temperature environment, preferably 2-8 ° C. High temperature can easily cause it to decompose or cause other chemical reactions, resulting in deterioration. Therefore, if conditions permit, it can be properly stored in refrigerated equipment.
Furthermore, the packaging must be tight. Packaging materials with good sealing performance should be used to prevent contact with air. Oxygen and moisture in the air will affect it. If using glass bottles, the cap must be tightened; if using plastic packaging, it must also ensure that there is no risk of leakage.
When transporting, it is necessary to avoid severe vibration and collision. Due to its relatively fragile chemical structure, excessive vibration or collision or damage to the packaging, which exposes it to adverse environments and may cause chemical reactions. The temperature and humidity in the transportation vehicle should also be controlled to maintain stable conditions as much as possible.
Transportation personnel should also be familiar with its chemical properties and safety precautions. In the event of an unexpected situation such as a leak, they should be able to take prompt and correct countermeasures to prevent the harm from expanding. In this way, O-trifluorophenylboronic acid can be guaranteed to maintain good quality and activity during storage and transportation.