Isoquinoline-5-boronic acid

Isoquinoline-5-boronic acid is an important reagent in organic synthesis. Its chemical properties are unique and have the typical characteristics of boric acid.
In this compound, the outer electronic structure of the boron atom makes it electronically deficient, so it has electrophilicity. Under suitable conditions, it can react with many nucleophiles. For example, under the catalysis of transition metals, it can be coupled with halogenated aromatics, halogenated olefins, etc., which is the classic Suzuki-Miyaura coupling reaction. Through such reactions, carbon-carbon bonds can be easily constructed, resulting in the synthesis of many complex organic molecules, which are widely used in pharmaceutical chemistry, materials science and other fields.
Furthermore, the isoquinoline ring part of isoquinoline-5-boronic acid confers a certain aromaticity and conjugate system. This conjugate structure not only affects the electron cloud distribution of the molecule, but also affects its physical and chemical properties. For example, the conjugate system enhances the stability of the molecule, and at the same time produces a specific absorption peak in the UV-visible spectral region, which facilitates its analysis and detection.
In addition, boric acid groups can be protonated or deprotonated under different pH environments. Under basic conditions, boric acid is easily deprotonated to form borate anions, enhancing its nucleophilicity; under acidic conditions, boric acid is protonated and its nucleophilicity is weakened. This acid-base response property makes isoquinoline-5-boronic acid potentially useful in some pH-sensitive reactions or material systems.

The common synthesis methods of isoquinoline-5-boronic acid are important in the field of organic synthesis. There are many methods, which are described in detail below.
First, halogenated isoquinoline is used as the starting material. Halogenated isoquinoline reacts with organometallic reagents, such as n-butyllithium, at low temperature and protected by inert gas, to form a lithiated intermediate. This intermediate has high activity and then reacts with borate esters, such as trimethyl borate, etc. After the reaction is completed, after hydrolysis treatment, isoquinoline-5-boronic acid can be obtained. This process requires fine control of reaction temperature, time and reagent dosage to obtain ideal yield and purity. < Br >
Second, the coupling reaction catalyzed by transition metals. With isoquinoline derivatives containing suitable substituents and boron sources, such as diphenylphosphine naloxyl borate, etc., in the presence of transition metal catalysts, such as palladium catalysts (such as tetra (triphenylphosphine) palladium, etc.) and ligands (such as tri-tert-butylphosphine, etc.), the reaction is heated in a suitable solvent. The reaction conditions are relatively mild and the selectivity is good, so the cost of the catalyst may be a consideration factor. In addition, the pH of the reaction system, the amount and type of catalyst have a significant impact on the reaction process and product yield.
Furthermore, there is a method for constructing boric acid groups through multi-step reactions starting from the isoquinoline matrix. The specific functionalization of isoquinoline is first carried out, and a substituent that can be converted into a boric acid group is introduced, and then a series of conversion reactions are carried out to finally produce isoquinoline-5-boronic acid. Although this path is a little complicated, the reaction strategy can be flexibly adjusted according to different needs to meet the expected product structure and purity requirements.
There are various methods for synthesizing isoquinoline-5-boronic acid, each with advantages and disadvantages. In practical applications, the appropriate synthesis path should be carefully selected according to factors such as raw material availability, cost, target product purity and yield.

Isoquinoline-5-boronic acid is useful in many fields. In the field of pharmaceutical creation, it is a key building block for the synthesis of novel drug molecules. With its unique structure, it can interact with specific targets in organisms, or it can help develop new drugs for the treatment of cancer, infection and nervous system diseases. Because organic boric acids often have good biological activity and low toxicity, isoquinoline-5-boronic acid is no exception.
In the field of materials science, it is also useful. Or it can participate in the preparation of functional materials, such as materials with special optical and electrical properties. By reacting with other compounds, unique molecular structures can be constructed to meet the needs of different material properties.
Furthermore, in the field of organic synthesis chemistry, isoquinoline-5-boronic acid, as an important organic synthesis reagent, can be used for the Suzuki-Miyaura coupling reaction and so on. Such reactions are an effective means to construct carbon-carbon bonds. Isoquinoline-5-boronic acid can react with substrates such as halogenated aromatics or olefins, and efficiently synthesize organic compounds with complex structures, providing powerful tools for the total synthesis of natural products and the preparation of new organic materials.
In addition, in the field of chemical analysis, its properties may be used to detect specific substances. Due to the fact that boric acid groups can form reversible binding with some hydroxyl-containing compounds, it is possible to design chemical sensors for specific analytes to achieve high selectivity and high sensitivity detection of targets.

The market price of Isoquinoline-5-boronic acid, that is, isoquinoline-5-boronic acid, often fluctuates due to various factors.
The first to bear the brunt is the purity of the product. If the purity is extremely high and almost flawless, the price will be high; if impurities are mixed in slightly, the purity will decrease slightly, and the price will also decrease accordingly. For example, those with a purity of more than 99% may be several percent higher than those with a purity of 95%.
Furthermore, the scale of production also affects the price. When the market demand exceeds the supply, the production scale will be difficult to expand for a while, and the price will rise like an arrow from the string; if the supply exceeds the demand, the manufacturer will have to reduce the price in order to seek sales.
In addition, the cost of raw materials is also the key. If the raw materials required for the synthesis of this acid are scarce and difficult to find, or the price rises for various reasons, the cost of isoquinoline-5-boronic acid will rise, and the price will also rise.
Brands and supply channels should not be underestimated. Well-known brands have strict quality control and a strong reputation, and their product prices are often higher than ordinary brands. And stable and high-quality supply channels may reduce intermediate links, making prices more competitive.
According to past market conditions, the price fluctuates between tens of yuan and hundreds of yuan per gram. However, the market is changing, and it is difficult to give a conclusive price. To know the current accurate price, it is advisable to consult chemical product suppliers or explore chemical product trading platforms to obtain the latest and accurate price information.

For isoquinoline-5-boronic acid, the preservation is essential, which is related to the stability of its quality and the constancy of its properties, and cannot be ignored. This product should be stored in a dry and cool place, away from direct sunlight. Cover the intensity of sunlight, or cause its chemical change, damage its pure quality.
And must be kept away from fire sources and oxidants. Due to its nature or contact with oxidized substances, it will cause danger. The storage place should be well ventilated to keep the air smooth and reduce the danger of gas accumulation.
And it should be stored when sealed. If exposed to air, water vapor may enter, causing deliquescence, damaging its structure, and changing its properties. As for the temperature, it is usually two to eight degrees. Low temperature can slow down the movement of its molecules, keep the quality normal, and prevent decomposition changes.
If in the laboratory, it is advisable to put special cabinets, classify and store them, and mark them for identification, so that they can be used, and prevent mistaken mixing, resulting in impurity or life risk. In this way, isoquinoline-5-boronic acid can be stored stably for a long time, and it is safe to use.