6-Bromopyridine-3-boronic acid

6-Bromopyridine-3-boronic acid is an important intermediate in organic synthesis and is widely used in many fields.
First, in the field of medicinal chemistry, this compound can be used as a key building block to build bioactive molecules. Due to its unique structure, it can participate in a variety of reactions and help synthesize drugs for the treatment of various diseases. For example, when developing anti-tumor drugs, it may be linked to other active fragments through specific reactions to build targeted anti-tumor compounds, which can inhibit tumor growth and spread by precisely acting on specific targets of tumor cells.
Second, in the field of materials science, 6-bromopyridine-3-boronic acid also plays an important role. It can be used to prepare functional materials, such as organic optoelectronic materials. The boron and bromine atoms in its structure endow the material with special electronic properties and reactivity, which can regulate the material's luminescence, conductivity and other properties. By rationally designing the reaction path and introducing it into the polymer skeleton, it is expected to prepare materials with excellent optoelectronic properties, which can be used in organic Light Emitting Diode (OLED), solar cells and other devices to improve the efficiency and stability of the device.
Furthermore, it can also be seen in the field of pesticide chemistry. As a key raw material for the synthesis of new pesticides, it can create high-efficiency, low-toxicity and environmentally friendly pesticide varieties. By reacting with other compounds containing nitrogen, oxygen and other functional groups, pesticides with unique mechanisms of action can be generated, which may interfere with the growth and development of pests, nervous system, etc., effectively control crop diseases and insect pests, and ensure the harvest of agricultural production.
In addition, in the basic research of organic synthetic chemistry, 6-bromopyridine-3-boronic acid is often used as a model compound to explore new reaction mechanisms and methods. Due to the difference in reactivity between bromine atoms and boric acid groups in its structure, it can provide chemists with rich reaction check points and research directions, help to develop novel organic synthesis strategies, and promote the development of organic synthetic chemistry.

The synthesis method of 6-bromopyridine-3-boronic acid has been explored by many parties throughout the ages. The following is a common method.
First, 6-bromopyridine is used as the starting material. First, 6-bromopyridine is reacted with n-butyllithium in an anhydrous ether or tetrahydrofuran in an inert solvent under a low temperature environment, such as -78 ° C. n-butyllithium is strongly basic and can capture the hydrogen atom of the bromine atom ortho-site on the pyridine ring to form the corresponding lithiated intermediate. This intermediate is highly active, and then borate esters, such as trimethyl borate or triisopropyl borate, are added. After the reaction, 6-bromopyridine-3-boronic acid can be obtained by hydrolysis with dilute acid, such as dilute hydrochloric acid or dilute sulfuric acid. In this process, the low temperature reaction conditions are extremely critical, which can effectively control the selectivity of the reaction and avoid the occurrence of side reactions.
Second, the method of transition metal catalysis is adopted. Using 6-bromopyridine and diphenylpyronacol borate as raw materials, under the action of palladium catalyst, such as tetra (triphenylphosphine) palladium (0), add an appropriate amount of base, such as potassium carbonate or potassium tert-butyl alcohol, and heat the reaction in an organic solvent, such as dioxane or toluene. Palladium catalysts can promote the coupling reaction of bromine atoms and borate ester groups to form the target product 6-bromopyridine-3-boronic acid. The conditions of this method are relatively mild and the yield is relatively impressive. However, attention should be paid to the dosage and recovery of palladium catalysts, because of its high cost.
Third, 6-bromopyridine-3-boronic acid is also prepared by bromination with pyridine-3-boronic acid as the starting material. Suitable brominating reagents, such as N-bromosuccinimide (NBS), can be used in the presence of initiators, such as benzoyl peroxide, in a suitable solvent, such as carbon tetrachloride. During the reaction, the amount of brominating reagent and the reaction temperature need to be controlled to prevent excessive bromination, so as to accurately obtain 6-bromopyridine-3-boronic acid.

6-Bromopyridine-3-boronic acid is an important reagent in the field of organic synthesis. In terms of its physical and chemical properties, they are described below.
Looking at its physical properties, under normal conditions, 6-bromopyridine-3-boronic acid is mostly white to off-white solid powder. This form is conducive to storage and access, and is easy to accurately weigh and feed in many organic reaction processes. Its melting point value is of great significance for identification and purity judgment. Generally speaking, the melting point is within a specific range. This range is roughly within a certain range due to slight differences in preparation methods and purity, so that the purity of the substance can be preliminarily determined. If the purity is high, the melting point range is relatively narrow and approaches the theoretical value; if it contains impurities, the melting point may decrease and the melting range becomes wider.
In terms of chemical properties, in 6-bromopyridine-3-boronic acid, boron atoms interact with pyridine rings and bromine atoms, resulting in unique chemical activities. Boric acid groups have typical Lewis acidity and can coordinate with compounds containing lone pair electrons, such as alcohols and amines. This property can be used as a guide group to guide the reaction when building complex organic structures. The activity of bromine atoms is also quite high. Under suitable conditions, it can participate in nucleophilic substitution reactions and react with many nucleophilic reagents, such as organometallic reagents, thiols, etc., so as to realize the functionalization of pyridine rings and provide an effective way for the synthesis of various pyridine derivatives.
In addition, 6-bromopyridine-3-boronic acid has a certain solubility in common organic solvents, such as dichloromethane, tetrahydrofuran, N, N-dimethylformamide, etc. This solubility provides convenience for its dispersion and reaction in organic synthesis reaction systems. According to specific reaction requirements, suitable solvents can be flexibly selected to optimize reaction conditions and improve reaction efficiency and product yield.

6-Bromopyridine-3-boronic acid is a commonly used reagent in organic synthesis. When storing and transporting, be sure to pay attention to many matters.
First word storage. This product should be stored in a dry, cool and well-ventilated place. Cover because of its certain chemical activity, wet environment is easy to cause reactions such as hydrolysis, which damages its quality. Temperature also needs to be controlled. Excessive temperature can promote decomposition or accelerate deterioration, so it is generally appropriate to refrigerate at low temperature, but it should also be careful not to freeze it, because freezing or causing changes in crystal structure will affect the use. Furthermore, it should be avoided to coexist with strong oxidants, strong bases and other substances to prevent violent chemical reactions from occurring and causing safety risks.
As for transportation, the packaging must be tight. Choose suitable packaging materials, which can effectively resist vibration and collision, and ensure a good seal to prevent leakage. During transportation, it is also necessary to maintain a stable environment, so as not to cause excessive temperature fluctuations. Transport personnel should be familiar with its chemical properties and emergency treatment methods. In case of leakage and other accidents, they can be properly disposed of in time to avoid causing greater harm. In short, when storing and transporting 6-bromopyridine-3-boronic acid, it is necessary to exercise caution and follow relevant norms to ensure its quality and safety.

6-Bromopyridine-3-boronic acid, a commonly used reagent in the field of organic synthesis, has important uses in many fields such as medicine, pesticides and materials science. Its market price range fluctuates due to a variety of factors.
Bear the brunt, the purity of the product has a significant impact on the price. For high-purity 6-bromopyridine-3-boronic acid, the preparation process is more complicated and requires fine purification steps, so the price is higher. Generally speaking, if the purity is above 98%, the price per gram may be in the hundreds of yuan. If the purity is about 95%, the price may be slightly reduced, or around 100 yuan per gram.
Furthermore, the market supply and demand relationship also affects its price. When the market demand for pharmaceuticals, pesticides and other related products is strong, the demand for 6-bromopyridine-3-boronic acid increases sharply, and the supply exceeds the demand, the price will rise. On the contrary, if the market demand is low and the supply is sufficient, the price may decline.
In addition, the manufacturer and the purchase quantity are also related to the price. Different manufacturers have different pricing due to differences in production processes and cost control. And the larger the purchase quantity, the manufacturer may give more discounts. If you buy in small quantities, such as only a few grams, the price may be relatively high; if you buy in bulk, such as kilograms, the price per gram may be much lower.
Overall, the market price range of 6-bromopyridine-3-boronic acid is relatively large. When purchased in small quantities and with high purity requirements, the price per gram may exceed 200 yuan; when purchased in bulk and with moderate purity requirements, the price per gram may be reduced to tens of yuan. The actual price still depends on the specific market conditions and trading conditions.