5-Hydroxypyridine-2-Boronic Acid Pinacol Ester

5-Hydroxypyridine-2-boronic acid pinacol ester is an important intermediate in organic synthesis. It has unique chemical properties and plays a key role in many organic reactions.
Looking at its structure, it contains a pyridine ring, a hydroxyl group and a boric acid pinacol ester group. This structure endows the compound with various reactivity. Pyridine ring, as an electron-rich aromatic ring, can participate in electrophilic substitution reactions. Hydroxyl groups are nucleophilic and can participate in esterification, etherification and other reactions. Boric acid pinacol ester groups are often used as organic boron reagents in organic synthesis, participating in Suzuki-Miyaura coupling and other reactions to construct carbon-carbon bonds.
In the coupling reaction of Suzuki-Miyaura, 5-hydroxypyridine-2-boronic acid pinacol ester and halogenated aromatics or olefins can efficiently form biaryl or alkenyl products under the action of palladium catalyst and base. The reaction conditions are mild and the selectivity is good, which is widely used in drug synthesis, material science and other fields.
Furthermore, the hydroxyl group can be modified. By reacting with acid chloride or acid anhydride, it can be converted into ester group, which can change the physical and chemical properties of the compound. Pyridine-2-boronic acid pinacol ester can also be formed by dehydration reaction, expanding its application in organic synthesis. 5-Hydroxypyridine-2-boronic acid pinacol ester exhibits rich chemical reactivity due to the synergistic action of various groups in its structure, providing many possibilities for organic synthesis chemists and playing an indispensable role in the construction of complex organic molecular structures.

The common synthesis methods of 5-hydroxypyridine-2-boronic acid pinacol ester are as follows:
First, 5-bromo-2-hydroxypyridine is used as the starting material. First, 5-bromo-2-hydroxypyridine and pinacol borane are reacted in organic solvents (such as toluene, dioxane, etc.) in the presence of palladium catalysts (such as tetra (triphenylphosphine) palladium, etc.), bases (such as potassium carbonate, etc.) and suitable ligands. This reaction follows the similar mechanism of Suzuki-Miyaura coupling reaction. The palladium catalyst activates pinacol borane, which makes the boron atom easily substituted with the bromine atom on 5-bromo-2-hydroxypyridine to form a carbon-boron bond, and then obtains the target product 5-hydroxypyridine-2-boronic acid pinacol ester. The reaction needs to be carried out under the protection of inert gas (such as nitrogen, argon) to avoid the oxidation of palladium catalysts and other catalysts, which affects the reaction process.
Second, 2-chloro-5-methoxypyridine is used as the raw material. First, it is reacted with magnesium chips to make Grignard reagent, and then Grignard reagent reacts with borate ester (such as trimethyl borate) to introduce boron atoms. Then, through demethylation reaction, it is treated with suitable reagents (such as boron tribromide, etc.) to convert the methoxyl group into a hydroxyl group, thereby obtaining 5-hydroxypyridine-2-boronic acid pinacol ester. The preparation of Grignard reagent in this route requires an anhydrous and oxygen-free environment to prevent side reactions of Grignard reagent with water and oxygen.
Third, 5-hydroxypyridine-2-formic acid is used as the starting material. First, it is esterified and converted into the corresponding ester. Then through a reduction reaction, such as the use of reducing agents such as lithium aluminum hydride, the ester group is reduced to an alcohol. Then the alcohol is converted into a suitable leaving group (such as a halogen atom, etc.), and finally reacts with pinacol borane under appropriate conditions to construct a boron ester structure and obtain the target product. Pay attention to the control of reaction conditions in each step to ensure high yield and selectivity.

5-Hydroxypyridine-2-boronic acid pinacol ester is an organoboron compound with a wide range of uses in the field of organic synthesis. In the field of medicinal chemistry, it is often used as a key intermediate to assist in the construction of many drug molecules. For example, when developing new antibacterial drugs, it can be used to participate in specific reactions, introduce key structural fragments, and optimize drug activity and selectivity.
In the field of materials science, it also has important applications. For example, the preparation of materials with special photoelectric properties can be used as functional structural units to endow materials with unique optical or electrical properties, which can be used in organic Light Emitting Diodes (OLEDs), solar cells and other devices. < Br >
In the field of catalytic chemistry, it can act as a ligand and cooperate with metal catalysts to promote the efficient progress of various chemical reactions. For example, in some coupling reactions, the reaction efficiency and selectivity are improved, and the reaction conditions are milder, which contributes to the development of organic synthetic chemistry.
With its unique chemical structure, this compound has shown important application value in many fields, promoting the progress and innovation of related technologies in various fields.

The market price of 5-hydroxypyridine-2-boronic acid pinacol ester varies for a variety of reasons. This is an important organic synthesis intermediate in the field of fine chemicals, and its price often fluctuates with factors such as market supply and demand, difficulty in preparation process, and raw material cost.
Looking at the market situation in the past, when the market demand is strong and supply is limited, its price often tends to rise. Because the preparation of this compound may require complicated synthesis steps and specific reaction conditions, and the cost of raw materials should not be underestimated. If the price of raw materials fluctuates, the price of 5-hydroxypyridine-2-boronic acid pinacol ester also fluctuates.
In addition, the price of products of different quality and purity is also very different. For high purity, the price is higher due to the need for more refined purification process and increased cost; while for lower purity, although it can meet some application scenarios that do not require strict purity, the price is relatively low.
Furthermore, the uniqueness of suppliers also makes the price difference. Well-known large manufacturers, due to their perfect production system and quality control, have stable product quality, and their prices may be slightly higher; while some small manufacturers compete for market share or at lower prices.
Overall, in order to determine the exact market price of 5-hydroxypyridine-2-boronic acid pinacol ester, it is necessary to check the chemical product trading platform in real time, or negotiate with relevant suppliers to obtain accurate price information.

5-Hydroxypyridine-2-boronic acid pinacol ester, this material should be stored in a dry, cool and well-ventilated place. Because it is quite sensitive to air and moisture, it is necessary to ensure tight isolation when storing.
When storing this product, choose a place away from fire and heat sources. Do not store it in a place with oxidants, acids, alkalis, etc., to prevent adverse reactions.
Storage containers should also be selected appropriately, strong and well sealed to avoid contact with outside air and moisture. Generally speaking, it is recommended to place it in an inert gas environment, such as nitrogen atmosphere, which can effectively reduce the risk of moisture and oxidation.
If it is stored for a long time, it should also be checked regularly to see if there are any signs of deterioration. Once any abnormalities are detected, such as color changes, precipitation, etc., it must not be reused, so as not to affect the subsequent use effect or even cause danger.
In short, proper storage of 5-hydroxypyridine-2-boronic acid pinacol ester requires attention from various aspects such as environment, container, and isolation, so as to ensure its quality is stable and ready for emergencies.