2-Aminopyridine-5-boronic acid pinacol ester

2-Aminopyridine-5-boronic acid pinacol ester, which is an important reagent in organic synthesis. Its chemical properties are unique and have a variety of characteristics.
Looking at its structure, it contains boron ester groups and aminopyridine structures. The boron ester part has relatively stable properties, but under specific conditions, it can exhibit active reactivity. In the case of nucleophiles, the boron ester bond can be broken, and then participate in many reactions, such as Suzuki coupling reaction. In this reaction, boron esters can react with halogenated aromatics or halogenated alkenes, and under the action of palladium catalysts and bases, realize the construction of carbon-carbon bonds, providing a key path for the synthesis of many types of complex organic molecules.
Aminopyridine moiety, the amino group is basic and can react with acids to form salts. And the amino group, as a power supply group, can affect the electron cloud density distribution of the pyridine ring, making the specific position on the pyridine ring more prone to electrophilic substitution reaction. For example, under suitable reaction conditions, halogenated reagents can selectively attack the position on the pyridine ring affected by the amino group to form halogenated products.
Furthermore, the physical properties of the compound also affect its chemical behavior. It has a certain solubility in organic solvents, which is conducive to participating in various organic reactions in solution systems.
In conclusion, 2-aminopyridine-5-boronic acid pinacol ester plays a key role in the field of organic synthesis due to its unique chemical structure. Through the clever use of its various chemical properties, it can realize the efficient synthesis of various complex organic compounds.

2-Aminopyridine-5-boronic acid pinacol ester has a wide range of uses. It is often used as a key intermediate in the field of organic synthesis. In the construction of complex organic molecular structures, it can effectively form carbon-carbon bonds through the coupling reaction of borate esters with many electrophilic reagents, such as Suzuki coupling reaction, which can effectively realize the formation of carbon-carbon bonds and help to synthesize pyridine derivatives with diverse structures. Such derivatives are of great significance in the process of pharmaceutical and pesticide creation. < Br >
In the field of pharmaceutical research and development, because the structure of pyridine is widely present in many active drug molecules, 2-aminopyridine-5-borate pinacol esters can be modified to introduce various pharmacoactive groups to develop drugs with novel mechanisms of action. For example, it may be used to synthesize inhibitors targeting specific disease targets, opening up new avenues for disease treatment.
In the field of materials science, materials with special photoelectric properties can be prepared by means of the reactions they participate in. By rationally designing the reaction path and integrating it into the polymer material or functional organic small molecule structure, it is expected to endow the material with unique optical and electrical properties, which can be applied to the preparation of organic Light Emitting Diodes, solar cells and other optoelectronic devices to improve device performance.

There are several methods for the synthesis of 2-aminopyridine-5-boronic acid pinacol ester as follows.
First, 2-amino-5-bromopyridine is used as the starting material. This compound reacts with pinacol borane in a suitable solvent under the action of palladium catalyst. The palladium catalyst used is usually tetrakis (triphenylphosphine) palladium (0), etc. The solvent can be selected from toluene, dioxane and the like. During the reaction, it needs to be heated to a certain temperature in an inert gas protective atmosphere, such as nitrogen or argon, usually between 80 and 110 degrees Celsius, and the reaction takes several hours to make the reaction fully proceed. After this step, the target product 2-aminopyridine-5-boronic acid pinacol ester can be generated.
Second, start from 2-nitro-5-bromopyridine. First, 2-nitro-5-bromopyridine is reacted with pinacol borane under a palladium-catalyzed system similar to the above to generate 2-nitropyridine-5-boronic acid pinacol ester, and then the nitro group is reduced. The reduction process can be used to react hydrogen in the presence of palladium-carbon catalyst in alcohol solvents, or to use chemical reduction systems such as iron powder and hydrochloric acid to convert nitro groups into amino groups to obtain 2-aminopyridine-5-boronic acid pinacol ester.
Furthermore, 2-aminopyridine is used as the starting material. The amino group is first protected to prevent it from interfering in the subsequent reaction, and suitable protective groups such as tert-butoxycarbonyl (Boc) can be selected. After protection, 2 - (Boc-amino) pyridine, under the action of strong bases such as butyl lithium, is lithium at a low temperature such as -78 ℃, and then added with borate pinacol ester reagent, nucleophilic substitution reaction occurs to generate protected 2-aminopyridine-5-borate pinacol ester, and finally the protective group is removed to obtain the target product 2-aminopyridine-5-borate pinacol ester.

When storing and transporting 2-aminopyridine-5-boronic acid pinacol ester, many matters need to be paid attention to. This is a crucial intermediate in organic synthesis. Due to its chemical properties, extreme caution should be used when storing and transporting.
Let's talk about storage first. First, it must be stored in a dry place. Because of its borate ester structure, it is easy to hydrolyze in contact with water, which in turn destroys the molecular structure and makes it ineffective. Therefore, it needs to be stored in a humidity-controlled environment. The relative humidity should be maintained at a low level, such as 40% or less. A well-sealed container, such as a glass bottle or a plastic bottle with a sealing gasket, should be used to prevent the intrusion of external water vapor. Second, temperature is also crucial. It should be stored in a cool environment, usually the temperature is preferably controlled at 2-8 ° C. If the temperature is too high, it may cause chemical reactions and reduce stability; if the temperature is too low, although the effect on its chemical properties is relatively small, it may change the state of the material and cause inconvenience to access. Third, keep away from oxidants and acids. The structure of amino and borate esters of 2-aminopyridine-5-boronic acid pinacol esters is easy to react with oxidants and acids, causing danger or causing product deterioration. When storing, it should be separated from such substances and kept at a certain distance.
Then transport. During transportation, the packaging must be stable. Shockproof and anti-collision materials need to be properly wrapped to prevent damage to the container during bumps and collisions, resulting in product leakage. If transported by road, avoid driving during high temperature periods to prevent excessive temperature in the compartment. If it is a long-distance transportation, environmental factors such as temperature and humidity should be monitored and regulated during the journey. In addition, transportation personnel also need to understand the basic characteristics of the substance and emergency treatment methods. In the event of unexpected situations such as leakage, they can be disposed of quickly and correctly to avoid serious consequences.

I am looking at the market price of 2 - Aminopyridine - 5 - boronic acid pinacol ester. This compound is a commonly used reagent in organic synthesis, and its price varies due to a variety of factors.
First, purity is the key element. For high purity, the preparation is difficult and the process is complicated, so the price is high. If the purity reaches more than 98%, the price is often expensive; and if the purity is slightly lower, such as about 95%, the price may decrease.
Second, the purchase volume has a great impact. If you buy in bulk, the supplier may give discounts due to economies of scale. If you buy several grams, the unit price may be high; if you buy several kilograms or more, the price per gram may be greatly reduced.
Third, the market supply and demand relationship also affects its price. If the demand is strong during a certain period and the supply is limited, the price will rise; conversely, if the supply exceeds the demand, the price may stabilize or fall.
Fourth, supplier differences also lead to different prices. Well-known and reputable suppliers, product quality is guaranteed, but the price may be high; some emerging or smaller scale, in order to compete for the market, the price may be more affordable.
According to past market conditions, small purchases (several grams), with a purity of 98%, may range from tens to hundreds of yuan per gram; if bulk purchases (kilogram level), each gram may be reduced to within tens of yuan. However, this is only a rough estimate. The actual price depends on the current supplier and depends on real-time market conditions.