6-Chloropyridine-3-boronic acid

6-Chloropyridine-3-boronic acid has unique chemical properties. This substance is a white to light yellow solid and plays an extraordinary role in the field of organic synthesis.
From the structural point of view, the boron atom is connected to the pyridine ring, giving it a variety of reactivity. In common reactions, it has typical properties of boric acid compounds. In case of base, it can form borate, which is often used to regulate the pH of the reaction system and affect the reaction process.
It can participate in the coupling reaction of Suzuki-Miyaura, which is a key reaction in organic synthesis. In this reaction, 6-chloropyridine-3-boronic acid and halogenated aromatics or olefins can form carbon-carbon bonds under the action of palladium catalyst and base, thereby constructing complex organic molecular structures, which is of great significance in the fields of drug development and materials science.
6-chloropyridine-3-boronic acid also exhibits certain electrophilicity and can react with nucleophiles. Due to the presence of chlorine atoms on the pyridine ring, it can enhance the electrophilicity of molecules and make nucleophilic substitution reactions more likely to occur. Chlorine atoms can be replaced by various nucleophiles to achieve group modification on the pyridine ring.
However, its stability requires specific conditions. In a humid environment, boric acid groups may hydrolyze, affecting their reactivity and purity, so they usually need to be stored dry.
In short, 6-chloropyridine-3-boronic acid has become an important intermediate in organic synthesis chemistry due to its diverse chemical properties, providing an effective way for the creation of new organic compounds.

6-Chloropyridine-3-boronic acid is widely used in the field of organic synthesis. First, it is often used as an arylation reagent. In the coupling reaction of Suzuki-Miyaura, this compound can form a carbon-carbon bond with halogenated aromatics or olefins under palladium catalysis. Due to the characteristics of boron atoms and chlorine atoms, it has specific reactivity, which can accurately construct complex aromatic systems. In the fields of medicinal chemistry and materials science, it can help create novel compound structures, such as synthesizing drug molecules with specific pharmacological activities, or preparing materials with special photoelectric properties.
Furthermore, in the field of heterocyclic compound synthesis, 6-chloropyridine-3-boronic acid is also a key intermediate. The existence of the pyridine ring endows it with unique electronic properties. By reacting with other reagents containing active functional groups, various thickened heterocyclic or polysubstituted pyridine derivatives can be constructed. This is of great significance in the creation of agricultural chemicals, and can develop high-efficiency and low-toxicity pesticide varieties.
Repeated, it is also used in surface modification of materials. By introducing 6-chloropyridine-3-boric acid into the surface of the material through appropriate chemical reactions, the chemical and physical properties of the material surface can be changed, such as improving the hydrophobicity and biocompatibility of the material. In the field of biomedical materials, it may enhance the interaction between materials and biological tissues, promote cell adhesion and proliferation, and provide a way for the improvement of tissue engineering materials.

The synthesis of 6-chloropyridine-3-boronic acid is an important topic in the field of organic synthesis. The synthesis path is described in detail in the following ancient Chinese style.
Usually, 6-chloropyridine-3-halide can be used. In this halide, the halogen atom can be bromine or iodine, and its activity is high, which is convenient for subsequent reactions. First, it is reacted with magnesium chips in an inert organic solvent such as anhydrous ether or tetrahydrofuran at an appropriate temperature. This process requires nitrogen protection to prevent air interference. The reaction of the two can generate Grignard reagents, namely 6-chloropyridine-3-magnesium halide. This Grignard reagent is extremely active and reacts violently in contact with water, so the operation process must be kept in an anhydrous environment.
Then, the generated Grignard reagent and borate esters, such as trimethyl borate or triethyl borate, are slowly added dropwise and mixed at low temperature. After the dropwise addition is completed, gradually heat up to an appropriate temperature to fully react. The borate and Grignard reagent undergo nucleophilic substitution reaction, and then 6-chloropyridine-3-borate intermediates are formed.
After the reaction is completed, the reaction system needs to be treated. An appropriate amount of dilute acid solution, such as dilute hydrochloric acid or dilute sulfuric acid, can be added to hydrolyze the borate ester intermediate to obtain the target product 6-chloropyridine-3-boronic acid.
Another synthetic idea can be achieved by coupling reaction catalyzed by transition metals. Using 6-chloropyridine-3-halide and pinacol biborate as raw materials, under the catalysis of palladium catalyst, such as tetra (triphenylphosphine) palladium, an appropriate amount of base, such as potassium carbonate, sodium carbonate, etc., is added to heat the reaction in an organic solvent. In this reaction, the palladium catalyst plays a key role in promoting the coupling between the halide and the pinacol ester of biborate to form the intermediate of 6-chloropyridine-3-borate pinacol ester. The subsequent hydrolysis step also uses an appropriate amount of acid to obtain 6-chloropyridine-3-boronic acid.
The above two methods have their own advantages and disadvantages. The raw materials of the Grignard reagent method are relatively common, but the operation requires strict anhydrous and oxygen-free; the conditions for the catalytic coupling reaction of transition metals are relatively mild, but the catalyst cost is relatively high. In actual synthesis, the appropriate method needs to be selected according to the specific needs and conditions.

6-Chloropyridine-3-boronic acid is a commonly used reagent in organic synthesis. When storing, many aspects need to be paid attention to.
The first environment is dry. This compound is prone to react in contact with water, causing its deterioration and inactivation. Due to the hydrophilicity of the boric acid group, the presence of water or the hydrolysis reaction will damage its structure and activity. Therefore, it should be stored in a dry place, and a desiccant, such as anhydrous calcium chloride, silica gel, etc. can be placed in the storage container to keep the environment dry.
The second is temperature. It should be stored in a low temperature environment, usually - 20 ° C to 0 ° C. Low temperature can reduce its chemical reaction activity and reduce the possibility of adverse reactions such as decomposition and polymerization. High temperature or promote its decomposition, causing purity and quality to decline.
Furthermore, avoid oxygen and air. 6-chloropyridine-3-boronic acid may react slowly with oxygen in the air, causing oxidative deterioration. To prevent this, it can be stored in an inert gas environment, such as nitrogen or argon atmosphere, or in a sealed container to reduce contact with air.
In addition, the choice of storage container is also critical. It is advisable to use a sealed container made of glass or plastic. Glass is chemically stable and does not react with compounds; specific plastic materials also have good tolerance and sealing, which can effectively resist water and gas penetration.
At the same time, clear labels are indispensable. The compound name, purity, storage date and other information should be marked in a prominent place in the container for tracking and management, and to prevent misuse.
In short, when storing 6-chloropyridine-3-boronic acid, it is necessary to ensure that it is dry, low temperature, protected from oxygen and air, choose a suitable container and clearly identify it, so as to ensure its quality and performance, and play its due role in organic synthesis.

The market price of 6-chloropyridine-3-boronic acid is difficult to determine. In the past, the price of chemical materials often changed due to various reasons, just like the situation is fickle.
The first to bear the brunt is the trend of supply and demand. If the industry has a strong demand for 6-chloropyridine-3-boronic acid, and there are few producers, its price will rise; on the contrary, if the supply exceeds demand, the price will automatically decline. In the past, many chemicals were subject to fluctuations in price due to changes in market supply and demand.
Furthermore, the price of raw materials also has a great relationship. The production of this product requires specific raw materials. If the price of raw materials is high, in order to ensure its profit, the price of the finished product will also increase; if the price of raw materials falls, the price of the finished product may also decrease accordingly. In the past, there were chemicals, but due to the lack of raw materials or the change in price, their own prices fluctuated greatly.
The technique of production also affects the price. If a new technique comes out, its cost can be reduced, and the price may be reduced; if the technique of production is stagnant, the cost is difficult to reduce, and the price is also difficult to reduce.
The difference in region is also a factor. In different places, the price may vary due to differences in taxes, transportation costs, etc. In places with convenient transportation and light taxes, the price may be lower than elsewhere.
Therefore, in order to know the exact market price of 6-chloropyridine-3-boronic acid, it is necessary to carefully consider the supply and demand, raw materials, technology and geographical conditions in order to obtain a more accurate number.