Benzothiophene-3-boronic acid

Benzothiophene-3-boronic acid is an important reagent in the field of organic synthesis. It has many unique chemical properties, which have a profound impact on the process of organic synthesis and the formation of products.
From the structural point of view, this compound contains a benzothiophene ring and a boric acid group. The benzothiophene ring is a fused heterocyclic structure, which endows it with certain aromatics and stability, giving the molecule a unique electron cloud distribution and spatial configuration. In the boric acid group, the outer electron configuration of the boron atom is special and electron-deficient. This property allows the boric acid group to interact with electron-rich species as a Lewis acid, and then exhibit special chemical activity.
In terms of reactivity, benzothiophene-3-boric acid performs well in coupling reactions, such as the Suzuki coupling reaction. In such reactions, boric acid groups can react with organic halides or pseudo-halides under the action of transition metal catalysts (such as palladium catalysts) to form new carbon-carbon bonds. This reaction has mild conditions and high selectivity. It is widely used in the construction of complex organic molecular structures and is of great value in drug synthesis, materials science and other fields.
In addition, its acidity cannot be ignored. Boric acid groups can undergo proton dissociation under certain conditions. Although the acidity is relatively weak, in some specific acid-base environments or catalytic systems, this weak acidity can affect the reaction equilibrium and reaction path.
In terms of solubility, benzothiophene-3-boronic acid exhibits moderate solubility in common organic solvents (such as dichloromethane, toluene, etc.) and polar solvents (such as water, alcohols, etc.), which facilitates its application in different reaction systems.
In terms of thermal stability, benzothiophene-3-boronic acid can maintain structural stability within the general experimental operating temperature range, but when the temperature is too high, the chemical bonds in the molecule may break, causing structural changes and decomposition. Therefore, temperature conditions should be paid attention to when storing and using.
In summary, benzothiophene-3-boronic acid plays a key role in organic synthesis and other fields due to its unique chemical structure, promoting the development of related scientific research and industrial production.

There are three common methods for the synthesis of benzothiophene-3-boronic acid. First, the halogenated benzothiophene method. First, the halogenated benzothiophene is taken, and palladium is used as a catalyst to react with borate esters in an alkaline environment. For example, starting with bromobenzothiophene, it is stirred at a suitable temperature in a palladium-catalyzed and potassium carbonate basic system with biborate pinacol ester. After coupling reaction, the corresponding borate ester is formed, and then hydrolyzed to obtain benzothiophene-3-boronic acid. In this process, the activity of palladium catalyst is key, the alkalinity is moderate and heavy, and the temperature is precisely controlled to obtain high yield.
Second, the metal-organic reagent method. Benzothiophene is treated with lithium reagent or magnesium reagent to make a specific position metallized and then reacted with borate ester. For example, at low temperature, butyl lithium interacts with benzothiophene to form a lithium intermediate, and then reacts with trimethyl borate to obtain the target product by hydrolysis. Among them, the reaction temperature is harsh, the metal reagent activity is high, and the operation needs to be in an anhydrous and anaerobic environment to prevent side reactions.
Third, the guide group auxiliary method. Introduce a guide group into benzothiophene, and with the help of its positioning effect, make the boronation reaction accurate to 3 positions. The guide group coordinates with the boron reagent to guide the selective addition of boron atoms. After the reaction is completed, remove the guide group. Although this method is a little complicated, it has good regional selectivity and high product purity. Each method has its advantages and disadvantages, and the actual application is selected according to factors such as raw materials, equipment, and cost.

Benzothiophene-3-boronic acid is widely used in various fields. It can be a key synthetic building block in the field of pharmaceutical creation. Through coupling reaction, it can be connected with various organic halides to construct complex drug molecular structures. Taking the development of anti-cancer drugs as an example, it can help researchers build compounds with specific biological activities, or find new anti-cancer drugs, bringing good news to patients.
In the field of materials science, it also shows unique functions. In the preparation of organic optoelectronic materials, the addition of benzothiophene-3-boric acid can optimize the photoelectric properties of the materials. For example, the preparation of organic Light Emitting Diode (OLED) materials may improve the luminous efficiency and stability of the materials, resulting in a wider color gamut and better image quality for OLED displays.
And in the field of catalysis, this compound also plays a role. It can act as a ligand and cooperate with metal catalysts to catalyze many organic reactions. Because of its unique structure, it may endow the catalyst with higher activity and selectivity, making the reaction conditions milder and the yield improved, helping to make chemical production more efficient and greener.

Benzothiophene-3-boronic acid, the price of this product in the market is really difficult to determine. Due to its price, it often changes for many reasons.
The first to bear the brunt is its quality. Those with high quality will naturally have a high price; if the quality is slightly inferior, the price will be slightly lower. Cover good quality things, for users, the utility is better, and they are willing to pay a high price.
Furthermore, the amount of output is also the key. If the output of this product is quite abundant in the market, and the supply exceeds the demand, the price may decline; on the contrary, if the output is scarce, the supply is in short supply, and the price will rise. Just like what is rare is expensive, this is common sense.
In addition, changes in market conditions also affect its price. The rise and fall of the business market and the increase and decrease of demand all make its price fluctuate. If the demand for benzothiophene-3-boronic acid in a certain industry increases sharply at a certain time, but the supply does not follow, the price will rise; if the demand is weak and the supply is surplus, the price will easily fall.
And the cost of production also affects the price. The price of raw materials, production labor costs, transportation tariffs, etc. are all included in the cost. If the cost is high, the merchant wants to protect his profit, and the price must be high; if the cost drops, the price may also drop.
Looking at the past, at some point due to the scarcity of raw materials, the cost soared, and the price of benzothiophene-3-boronic acid also rose sharply. At another time, technological innovation, production increased greatly, and the price gradually declined.
Therefore, in order to know the current market price of benzothiophene-3-boronic acid, it is necessary to carefully observe the quality, production, market conditions, and cost factors, and pay attention to changes in market conditions in real time, in order to obtain a more accurate price.

Benzothiophene-3-boronic acid should be stored in a cool, dry and well-ventilated place. This is because of its active nature, easy to react with water, moisture, etc., causing deterioration and failure. Therefore, avoid moisture to prevent its hydrolysis and damage.
The temperature at the storage place should also be paid attention to, and it should be controlled at a moderate low temperature, usually not exceeding 25 ° C. Excessive temperature may cause its chemical reaction rate to increase and accelerate deterioration.
Furthermore, it should be stored in isolation from oxidants, acids, bases, etc. Benzothiophene-3-boronic acid is chemically active, and coexistence with them can easily trigger chemical reactions, or cause danger, or cause quality deterioration.
The packaging must be tight to prevent the intrusion of external environmental factors. After taking it, seal the package and never expose it to the air for a long time. Properly stored, the benzothiophene-3-boronic acid can maintain good quality and performance within a certain period of time for subsequent experiments and production.