2-Methylpyridine-4-boronic acid pinacol ester

2-Methylpyridine-4-boronic acid pinacol ester is an important intermediate in organic synthesis. It has many unique chemical properties.
Looking at its structure, the interaction between the pyridine ring and the boronyl ester group endows the compound with various reactivity. In the nucleophilic substitution reaction, the nitrogen atom on the pyridine ring can exert weak basicity and coordination ability because of its lone pair of electrons, and can interact with electrophilic reagents. At the same time, the boronyl ester group can participate in many organic boron chemical reactions, such as the Suzuki-Miyaura coupling reaction, due to the lack of electron properties of the boron atom. In this reaction, 2-methylpyridine-4-boronic acid pinacol ester can form carbon-carbon bonds with halogenated aromatics or olefins under palladium catalysis, which is widely used in the field of constructing complex aromatic structures.
In terms of physical properties, the compound is usually solid and has relatively high stability. It has a certain solubility in common organic solvents such as dichloromethane and toluene. This property is convenient for its operation and application in organic synthesis reaction systems.
The uniqueness of its chemical properties is also reflected in the requirements for reaction conditions. In many reactions, specific catalysts, bases, and suitable temperatures and reaction times are required to achieve ideal reaction results. For example, in the coupling of Suzuki-Miyaura, the activity of palladium catalyst, the type and amount of base have a great influence on the reaction process and yield.
The chemical properties of 2-methylpyridine-4-boronic acid pinacol ester make it have important application value in many fields such as medicinal chemistry and materials science, and provide a powerful tool for the synthesis of complex organic molecules.

2-Methylpyridine-4-boronic acid pinacol esters are widely used in the field of organic synthesis. They are mainly used to construct carbon-carbon bonds and carbon-heteroatomic bonds.
As far as the construction of carbon-carbon bonds is concerned, Suzuki-Miyaura coupling reaction is often involved. In this reaction, 2-methylpyridine-4-boronic acid pinacol esters can be successfully coupled with halogenated aromatics or halogenated olefins in the presence of palladium catalysts and bases, resulting in the formation of a series of biaryl or alkenylpyridine compounds containing pyridine structures. Such compounds are of great significance in the field of medicinal chemistry, and the core structure of many bioactive drug molecules is built by this method. For example, the synthesis of key intermediates of some drugs used to treat cardiovascular diseases or tumors relies on this reaction, which is obtained by coupling 2-methylpyridine-4-boronic acid pinacol esters with specific halogenated aromatic hydrocarbons.
This compound is also useful in forming carbon-heteroatomic bonds. It can react with nucleophiles containing heteroatoms such as nitrogen, oxygen, and sulfur. For example, by reacting with nitrogen-containing heterocyclic compounds, structures combining pyridine and other nitrogen-containing heterocycles can be formed. Such structures have applications in the field of materials science and can be used as components of organic Light Emitting Diode (OLED) materials. Due to their unique electronic structure and molecular configuration, the materials are endowed with specific photoelectric properties, such as high luminous efficiency and good stability.
In addition, 2-methylpyridine-4-boronic acid pinacol esters can also be used to synthesize functionalized ligands. After complexing with metal ions, these ligands exhibit unique catalytic activity and selectivity in catalytic reactions. It can regulate the electron cloud density and steric resistance of metal centers, which in turn affect the rate of catalytic reactions and the selectivity of products. In some asymmetric catalytic reactions, metal catalysts modified with such ligands can efficiently prepare optically active compounds, which are of great value in chiral drug synthesis and fine chemical preparation.

There are several ways to prepare 2-methylpyridine-4-boronic acid pinacol ester.
First, 2-methylpyridine is used as the starting material. First, 2-methylpyridine is treated with n-butyl lithium at low temperature. N-butyl lithium is strongly basic and can capture hydrogen atoms at specific positions on the pyridine ring to form corresponding lithium reagents. Subsequently, borate esters, such as pinacol borate, are added. The lithium reagent undergoes nucleophilic substitution with the borate ester. After subsequent treatment such as hydrolysis, the target product 2-methylpyridine-4-boronic acid pinacol ester can be obtained. This process requires attention to the maintenance of low temperature conditions to ensure the regioselectivity of the reaction and avoid side reactions.
Second, the method of transition metal catalysis can be used. Using 2-methyl-4-halopyridine and pinacol borate as raw materials, in the presence of transition metal catalysts such as palladium and nickel, the reaction is carried out under the action of suitable ligands and bases. The halogen atom of halopyridine is coupled with pinacol borate under the catalysis of transition metals. The ligand can adjust the electron cloud density and steric resistance of transition metals to enhance the activity and selectivity of the catalyst. The function of the base is to neutralize the hydrogen halide generated by the reaction and promote the positive progress of the reaction. The conditions of this method are relatively mild, and the yield is considerable.
Third, we can also start from pyridine-4-boronic acid pinacol ester. The methylation reaction of pyridine-4-boronic acid pinacol ester is carried out first. Appropriate methylation reagents, such as iodomethane or dimethyl sulfate, are selected. Under the catalysis of alkali, the methyl group of the methylation reagent reacts with the nitrogen atom or other suitable positions on the pyridine ring. After optimizing the reaction conditions, 2-methyl pyridine-4-boronic acid pinacol ester can be obtained. This process requires careful selection of the type and dosage of bases to prevent side reactions such as excessive methylation.

2-Methylpyridine-4-boronic acid pinacol ester, when storing and transporting, it is necessary to pay attention to many matters.
This compound is quite sensitive to moisture, so when storing, it must be placed in a dry place, and sealed tightly to prevent moisture intrusion and hydrolysis. If the ambient humidity is high, its stability will be greatly affected, or the original chemical activity will be lost.
In addition, it also requires temperature. It should be stored in a cool place to avoid high temperature. High temperature can easily cause thermal decomposition of the compound, which will damage its quality and purity. During transportation, it is also necessary to ensure that the ambient temperature is suitable and avoid direct sunlight, because sunlight exposure can cause local temperature to rise and trigger adverse chemical changes.
In addition, 2-methylpyridine-4-boronic acid pinacol ester may have certain chemical activity and cannot be stored and transported with strong oxidants, strong acids, strong bases and other substances. Contact with these substances can easily cause violent chemical reactions, or cause dangerous accidents such as combustion and explosion.
During transportation, the packaging must be sturdy and reliable, capable of withstanding certain physical shocks, and preventing the leakage of compounds caused by package damage. Once leaked, it will not only cause material loss, but also cause harm to the environment and human body due to its chemical properties. When handling, operators should also handle it with care to avoid violent vibrations and collisions.
In short, the storage and transportation of 2-methyl pyridine-4-boronic acid pinacol ester requires efforts in moisture prevention, temperature control, avoiding contact with contraindications, and ensuring stable packaging to ensure its quality and transportation safety.

The price of 2-methylpyridine-4-boronic acid pinacol ester on the market is difficult to hide. Its price often changes for various reasons, just like ancient business affairs, and is also influenced by many factors.
First, the purity of this product is quite related to the price. If the purity is high, it is almost flawless, just like a carefully selected treasure, its price is high; if the purity is low, the impurities are slightly more, and it is like a adulterated inferior product, the price will definitely drop.
Second, the supply and demand situation of the market is also the key. If there are many people who ask for it, but the supply is small, just like the rare and rare goods in ancient times, the price will rise; if there is an oversupply, it is like the goods are piled up like mountains and no one cares, and the price will fall.
Third, the cost of making this thing also affects its price. If the price of raw materials is as high as gold, and the preparation techniques require a lot of manpower and material resources, it is like a difficult task to be carefully carved. If the cost is high, the price will also be high; on the contrary, if the cost is low, the price may be close to the people.
Fourth, different suppliers have different prices. Reputable suppliers are known for their quality, just like time-honored brands, and their prices may be relatively high; while emerging or unknown suppliers are competing for market share, and their prices may be more attractive.
According to past commercial examples, their prices fluctuate widely. At least it can be tens of yuan per gram, and at most it can reach hundreds of yuan per gram, or even higher. To know the exact market price, you need to consult the suppliers in detail to compare their prices and quality, so that you can get a suitable price.