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What are the main uses of 2- (Trifluoromethyl) Benzeneboronic Acid?
2 - (trifluoromethyl) phenylboronic acid has a wide range of uses. It is often used as an important intermediate in the field of organic synthesis. It can participate in the Suzuki-Miyaura coupling reaction, which is a key method for constructing carbon-carbon bonds. In this reaction, 2 - (trifluoromethyl) phenylboronic acid can react with halogenated aromatics or alkenyl halides, and under the action of palladium catalyst and base, efficiently generate trifluoromethyl-containing biaryl or alkenyl aromatic hydrocarbons. Such compounds are of great significance in medicinal chemistry, and many biologically active drug molecules contain such structural fragments.
In the field of materials science, it also has important uses. Due to the unique properties of trifluoromethyl, materials containing 2- (trifluoromethyl) phenylboronic acid-derived structures may have special electrical, optical or thermal properties. For example, it can be used to prepare organic semiconductor materials with specific optoelectronic properties. Such materials may exhibit excellent performance in organic Light Emitting Diode (OLED), organic photovoltaic cells and other devices, which helps to improve the efficiency and stability of the device.
In addition, in the field of agricultural chemistry, with the help of its participation in the synthesis of compounds containing trifluoromethyl, or with unique biological activities, it can be developed into new pesticides for pest control and protection for agricultural production. Overall, 2 - (trifluoromethyl) phenylboronic acid plays a key role in many fields, promoting the development and progress of various fields.
2- (Trifluoromethyl) Benzeneboronic Acid
There are several common methods for synthesizing 2 - (trifluoromethyl) phenylboronic acid.
One is the halogenated aromatic hydrocarbon method. Using 2 - (trifluoromethyl) halobenzene as the starting material, at low temperature, it interacts with metal magnesium to form Grignard's reagent. This process needs to be carried out in an inert solvent such as anhydrous ether or tetrahydrofuran, and the reaction system must be anhydrous and oxygen-free. Subsequently, the generated Grignard's reagent is reacted with borate ester, and after hydrolysis, the target product 2 - (trifluoromethyl) phenylboronic acid can be obtained. The reaction principle is based on the strong nucleophilic properties of Grignard's reagents, which can undergo nucleophilic substitution with borate esters. After hydrolysis, borate esters are converted into bor
Second, palladium-catalyzed coupling method. Using 2 - (trifluoromethyl) halobenzene and diphenylboronyl alcohol ester as raw materials, under the catalysis of palladium catalyst such as tetra (triphenylphosphine) palladium, the reaction system often uses toluene, dioxane, etc. as solvents, potassium carbonate, sodium carbonate, etc. as bases. The palladium catalyst can activate halogenated aromatics and borate esters, and promote the coupling reaction of the two to generate 2 - (trifluoromethyl) phenylboronic acid phenylboronyl alcohol ester, which is then hydrolyzed to obtain the target product. This method has good selectivity and high yield, and is widely used in the field of organic synthesis.
Third, metal lithium reagent method. 2- (trifluoromethyl) halobenzene is first reacted with metal lithium reagents such as butyl lithium to form lithium reagent intermediates. This step needs to be operated in a low temperature and anhydrous and oxygen-free environment. After that, the intermediate is reacted with borate and hydrolyzed to obtain 2- (trifluoromethyl) phenylboronic acid. This method has high reactivity, but it requires strict reaction conditions and requires careful operation.
The above synthesis methods have their own advantages and disadvantages. In practical application, the appropriate synthesis path should be carefully selected according to the availability of raw materials, the controllability of reaction conditions, the purity and yield requirements of the target product, and other factors.
What are the Physical Properties of 2- (Trifluoromethyl) Benzeneboronic Acid
2-%28Trifluoromethyl%29Benzeneboronic Acid is 2 - (trifluoromethyl) phenylboronic acid, which has the following physical properties:
It is mostly white to light yellow crystalline powder at room temperature, and its texture is fine. This state is conducive to storage and use. In many experimental operations and industrial processes, this form can ensure its dispersibility and reaction contact area, which has a great impact on the subsequent reaction process.
2 - (trifluoromethyl) phenylboronic acid has a melting point between 128 - 132 ° C, and the melting point is in this range, indicating that the intermolecular force is moderate. When heated to this temperature range, the molecules are energized enough to overcome the lattice energy, and the lattice structure disintegrates and melts into a liquid state. This melting point property is of great significance in separation, purification and control of specific reaction conditions. It can achieve phase transformation of substances by precise temperature control, and achieve the purpose of separation or participation in specific reactions.
The solubility of this substance is also worthy of attention. It is slightly soluble in water, but soluble in common organic solvents such as dichloromethane, ether, toluene, etc. Good solubility in organic solvents makes it widely used in the field of organic synthesis. Organic reactions are mostly carried out in organic solvent systems, and its solubility ensures that it can be fully mixed with other organic reactants, and the probability of intermolecular contact is greatly increased, thereby promoting the efficient progress of the reaction. It has poor solubility in the aqueous phase, but it can be used in the design of heterogeneous reaction systems involving the aqueous phase to realize phase transfer catalysis or specific phase separation processes according to this characteristic.
In addition, 2 - (trifluoromethyl) phenylboronic acid has certain stability and can maintain its own chemical structure and properties under conventional environmental conditions. However, when encountering specific chemicals such as strong oxidizing agents and strong bases, the stability is damaged, and chemical reactions are prone to occur, resulting in structural and property changes. When storing and using, it is necessary to avoid contact with such substances, and choose suitable storage conditions and packaging materials to ensure the stability of its physical properties and chemical activities.
What are the chemical properties of 2- (Trifluoromethyl) Benzeneboronic Acid
2-%28Trifluoromethyl%29Benzeneboronic Acid is 2 - (trifluoromethyl) phenylboronic acid, and its chemical properties are as follows:
This compound contains boron-oxygen bonds and has boric acid-like properties. In water, borate can interact with water molecules to release protons, which is weakly acidic. This acidity is derived from the lack of electrons in boron atoms and can accept lone pair electrons of oxygen atoms in water molecules, which increases the concentration of hydrogen ions in the system.
2 - (trifluoromethyl) phenylboronic acid, trifluoromethyl is a strong electron-withdrawing group, which affects the electron cloud density of the benzene ring. Due to its electron-withdrawing effect, the electron cloud density of the benzene ring decreases, which changes the reaction activity of this compound with electrophilic reagents, and increases the difficulty of electrophilic sub Compared with general phenylboronic acid, due to the strong electron absorption of trifluoromethyl, the electron cloud density at the check point of the reaction decreases, and it is less prone to electrophilic substitution, especially in the ortho and para-positions on the benzene ring.
The boron-oxygen bonds in this compound can participate in a variety of organic reactions, such as Suzuki coupling reaction. In this reaction, 2 - (trifluoromethyl) phenylboronic acid and halogenated aromatic hydrocarbons can form carbon-carbon bonds under the action of palladium catalyst and base, which can be widely used in drug synthesis, materials science and other fields to provide an effective way to construct complex organic molecular structures.
In addition, 2 - (trifluoromethyl) phenylboronic acid is sensitive to air and humidity. When the humidity is high, the boric acid group may undergo side reactions such as hydrolysis, which will affect its stability and reactivity. Therefore, it is necessary to pay attention to moisture-proof storage, usually stored in a dry inert gas environment.
2- (Trifluoromethyl) Benzeneboronic Acid Storage and Transportation
2-%28Trifluoromethyl%29Benzeneboronic Acid is 2 - (trifluoromethyl) phenylboronic acid. When storing and transporting this substance, many things need to be paid attention to.
Let's talk about storage first. Because of its nature, it needs to be placed in a cool and dry place. If it is in a warm and humid environment, it is easy to deteriorate. Just as the ancient books say "things should be hidden in a dry and cool place to prevent them from spoiling", the same is true. It needs to be stored separately from oxidizing agents, acids, and alkalis, and cannot be mixed. Because these substances come into contact with it or react chemically, they lose their properties. Just like the ancients said "different species avoid each other to prevent accidents". Where it is stored, there should be suitable materials to contain leaks, just in case there is a leak, and it can be dealt with in time.
Let's talk about transportation. During transportation, make sure that the container does not leak, collapse, fall, or be damaged. Just like the ancients escorting precious goods, care must be taken to ensure its integrity. Vehicles used during transportation should be driven according to the specified route, and do not stop in densely populated areas and residential areas. Because if the substance leaks, it may endanger the safety of everyone. During transportation, it should be protected from sun exposure, rain exposure, and high temperature. Exposure to the hot sun, rain exposure, and high temperature may affect its quality, just like the ancients transported vulnerable items, which needed to be protected from wind and rain and avoid high temperature. When loading and unloading, operators should load and unload lightly, and strictly prohibit touching and heavy pressure to ensure the integrity and safety of 2 - (trifluoromethyl) phenylboronic acid.