pyridine-3-boronic acid

Pyridine-3-boronic acid has a wide range of uses. In the field of organic synthesis, this is a crucial intermediate. First, it can participate in the Suzuki coupling reaction. In this reaction, pyridine-3-boronic acid can be coupled with halogenated aromatics or halogenated olefins under the action of palladium catalysts and bases to form carbon-carbon bonds. With this reaction, many biaryl compounds with specific structures can be synthesized, which have important applications in pharmaceutical chemistry and materials science. In the field of drug research and development, the structural design of many drug molecules requires the construction of a precise carbon-carbon skeleton. The biaryl structure synthesized by the Suzuki coupling reaction can often endow drugs with unique biological activities and pharmacological properties. Pyridine-3-boronic acid plays a key role in this process.
Second, in the field of materials science, pyridine-3-boronic acid can be used to prepare functional materials. For example, materials with photoelectric properties can be synthesized through their reaction with specific organic molecules. Such materials may be used in organic Light Emitting Diodes (OLEDs), solar cells and other devices. The boron atom and pyridine ring structure introduced by pyridine-3-boronic acid can regulate the electron cloud distribution and energy level structure of the material, thereby optimizing the photoelectric properties of the material and improving the efficiency and stability of the device.
Third, in the field of biochemistry, pyridine-3-boronic acid can interact specifically with biomolecules such as carbohydrates due to its special structure. Taking advantage of this property, a sensor for sugar detection can be designed. By modifying pyridine-3-boronic acid on the surface of the sensor, when it comes into contact with sugar molecules, it can initiate physical or chemical signal changes of the sensor, realizing rapid and sensitive detection of carbohydrates, which has potential application value in disease diagnosis.

Pyridine-3-boronic acid is an important compound in organic chemistry. Its physical properties are quite characteristic, let me explain in detail.
Looking at its appearance, it is often in the state of white to light yellow crystalline powder. The characteristics of this color state can be used for the first identification. Its properties are stable at room temperature and pressure, and it may be dangerous in case of hot topics, open flames, or contact with strong oxidants. Caution must be taken.
When it comes to the melting point, the melting point of pyridine-3-boronic acid is between 140-144 ° C. The melting point is the critical temperature at which a substance changes from a solid state to a liquid state. This characteristic is of great significance in the experimental process of purification and identification of compounds. Knowing the melting point can determine the purity of the substance. If the purity is high, the melting point range is narrow and close to the theoretical value; if it contains impurities, the melting point is reduced and the range is widened.
Furthermore, solubility is also a key physical property. Pyridine-3-boronic acid is slightly soluble in water, but soluble in common organic solvents such as ethanol, ether, dichloromethane, etc. This solubility property plays a guiding role in the selection of solvents for organic synthesis reactions and the separation of products. Selecting a suitable solvent can make the reaction proceed smoothly and the product can be effectively separated.
In addition, the density of pyridine-3-boronic acid also has its value, which is about 1.32g/cm ³. In terms of density, the mass of the substance per unit volume, although not the primary consideration in general experimental operations, cannot be ignored in specific scenarios, such as material measurement, reaction system design, etc.
In short, the physical properties of pyridine-3-boronic acid, such as appearance, melting point, solubility, density, etc., are important bases for the research and application of organic chemistry, and play an indispensable role in experimental operations and synthesis process optimization in related fields.

There are many ways to synthesize pyridine-3-boronic acid. One method is to use pyridine-3-halide as the starting material. First, pyridine-3-halide interacts with metal magnesium to form Grignard reagent. This process requires careful operation in an anhydrous and oxygen-free environment, using ether or tetrahydrofuran as a solvent, so that the halide and magnesium powder fully react to form an active Grignard reagent. Then, the Grignard reagent meets the borate ester, and through the nucleophilic substitution reaction, part of the structure of the borate ester is connected, and then the intermediate of pyridine-3-boric acid is obtained. Finally, through the hydrolysis step, the intermediate is treated with dilute acid to hydrolyze the borate ester into boric acid, thereby obtaining the product of pyridine-3-boronic acid.
Another method can be borrowed from the principle of Suzuki reaction. Pyridine-3-halide and borate are reacted in a basic environment under the catalysis of palladium catalyst. The commonly used palladium catalyst is tetrakis (triphenylphosphine) palladium (0), and the base can be selected as potassium carbonate, sodium carbonate, etc. This reaction needs to be carried out in a suitable organic solvent, such as dioxane, toluene, etc. During the reaction, the coupling reaction between the halide and the borate ester occurs under the synergistic action of the catalyst and the base, and the pyridine-3-boronic acid is directly generated. This method has relatively mild conditions and high selectivity. However, the catalyst may be expensive, and the reaction equipment and operation requirements are also strict.
Furthermore, pyridine is used as the starting material, and lithium atoms are introduced into the 3-position of pyridine through a lithification reaction. This lithification reaction usually treats pyridine with a strong base such as n-butyl lithium at low temperature, so that the hydrogen of the 3-position of pyridine is replaced by lithium. Subsequently, the lithiated pyridine is reacted with borate ester to form boron-containing intermediate, and then hydrolyzed to obtain pyridine-3-boronic acid. Although this path is a little complicated, it requires relatively wide selectivity of raw materials, and it is also an effective synthesis strategy under certain circumstances.

For pyridine-3-boronic acid, be sure to pay attention to many matters during storage and transportation.
First, storage, because of its lively nature, should be placed in a cool and dry place. Avoid high temperatures, cover high temperatures can easily cause chemical reactions and damage its quality. And it must be kept away from fire sources and oxidants. Pyridine-3-boronic acid encounters oxidants, it may react violently and even cause danger. Furthermore, the storage place should be well ventilated to prevent the accumulation of harmful gases. Packaging should also be tight to avoid contact with air and moisture. Because it is easy to react with water and will deteriorate if it is damp, the packaging needs to be moisture-proof.
As for transportation, the same cannot be slack. The transport container must be sturdy and can withstand a certain pressure and vibration to prevent it from being damaged and leaking. And the appropriate temperature should be maintained during transportation, and it should not be too high or too low. Too high will increase the risk of reaction, and too low will cause its physical state to change. When handling, it is necessary to handle it with care to avoid violent collisions. Furthermore, the transporter should be familiar with its characteristics and emergency treatment methods, and in case of leakage and other conditions, it can be disposed of quickly and properly. In short, the storage and transportation of pyridine-3-boronic acid requires careful treatment of all aspects to ensure its safety and quality.

The price of pyridine-3-boronic acid varies for many reasons in the market. First, it is related to purity. For those with high purity, the preparation process is complicated and difficult, expensive, and the price is high; for those with low purity, the process is slightly simpler, the cost is saved, and the price is also low. Second, the scale of production is different. Large-scale producers, with the benefit of scale, the cost may be reduced, and the market price may be close to the people; small-scale producers, the cost is high, and the price is also higher. Third, the supply and demand of the city are also the main reasons. If there are many people who want it, the supply is small, and the price will rise; if the supply exceeds the demand, the price may fall.
Looking at the market conditions of the past, the price per gram of a product with a purity of about 97% may be between tens of yuan and 100 yuan. However, in the chemical industry market, the price of raw materials, changes in processes, and regulations of politics can all cause fluctuations in its price. And the market in various places varies in price due to logistics, taxes, etc. Therefore, in order to know the real-time price, it is advisable to consult the suppliers, traders, or trading platforms of chemical raw materials to obtain accurate information.