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What is the chemistry of 4-Methylthiophene-3-boronic acid?
4-Methylthiophene-3-boronic acid is an important reagent in the field of organic synthesis. Looking at its chemical properties, this compound contains a boric acid group (-B (OH) -2), which has unique reactivity.
The boric acid group is Lewis acidic and can coordinate with molecules or ions with lone-pair electrons. In many organic reactions, it can interact with groups containing lone-pair electrons such as hydroxyl groups and amino groups, thereby promoting the reaction.
It plays a significant role in Suzuki coupling reactions. In such reactions, 4-methylthiophene-3-boronic acid can be coupled with halogenated aromatics or olefins in the presence of palladium catalysts and bases to form carbon-carbon bonds, thereby effectively constructing complex organic molecular structures, which are widely used in drug synthesis, materials science and other fields. The methyl group on the thiophene ring also affects its chemical properties. Methyl groups are electron-supplying groups, which can increase the electron cloud density of the thiophene ring and make the thiophene ring more prone to electrophilic substitution reactions.
At the same time, the physical properties of 4-methylthiophene-3-boronic acid, such as solubility in common organic solvents, also affect its application in reactions. It has a certain solubility in some polar organic solvents such as dichloromethane, N, N-dimethylformamide, which facilitates the operation of related reactions.
Due to its active chemical properties and unique structure, 4-methylthiophene-3-boronic acid plays a key role in the stage of organic synthesis, assisting researchers in creating various novel and valuable organic compounds.
What are the synthetic methods of 4-Methylthiophene-3-boronic acid?
There are several methods for synthesizing 4-methylthiophene-3-boronic acid as follows.
First, 4-methylthiophene is used as the starting material. First, 4-methylthiophene is reacted with butyllithium at low temperature. Butyllithium is strongly basic and can capture hydrogen atoms at specific positions on the thiophene ring to form carbon negative ions. This carbon negative ion has high activity and then reacts with borate esters, such as trimethyl borate. After the reaction is completed, the borate ester is hydrolyzed to form the target product 4-methylthiophene-3-boronic acid through a hydrolysis step. In this process, the low temperature reaction conditions are extremely critical, which can ensure the regioselectivity of the reaction, so that the lithium reaction can occur at the desired position.
Second, halogenated 4-methylthiophene can also be used as a raw material. For example, bromo4-methylthiophene is used as a coupling reaction with diphenacol borate in the presence of a palladium catalyst. The palladium catalyst can activate the carbon-halogen bond and promote its binding to the borate ester. In the reaction system, a suitable base needs to be added to promote the reaction. The base can neutralize the hydrogen halide generated by the reaction and push the reaction equilibrium to move towards the product direction. After the reaction is completed, pure 4-methylthiophene-3-boronic acid can be obtained through separation and purification.
Third, the method of metal-organic chemical vapor deposition (MOCVD) is used. The organometallic compound containing 4-methylthiophene structure and the gaseous precursor containing boron react chemically on the surface of the substrate at a specific temperature, pressure and carrier gas environment. The gaseous precursor adsorbs and reacts on the surface of the substrate to gradually form 4-methylthiophene-3-boronic acid. This method can precisely control the growth and deposition of the product, and is suitable for synthesis under specific needs.
Where is 4-Methylthiophene-3-boronic acid used?
4-Methylthiophene-3-boronic acid, a key reagent in organic synthesis, is useful in many fields.
In the field of medicinal chemistry, it plays a pivotal role. The synthesis of many drug molecules often relies on this reagent. The structure of Geiinthiophene and boric acid gives it unique reactivity and selectivity. Through specific chemical reactions, such as Suzuki-Miyaura coupling reaction, it can be cleverly combined with substrates such as halogenated aromatics to build a complex drug molecular skeleton. For example, when synthesizing some anti-tumor drugs, 4-methylthiophene-3-boronic acid can be used as a key building block to help build biologically active core structures, thus opening up new paths for drug research and development.
In the field of materials science, it also has value that cannot be ignored. In the preparation of optoelectronic materials, this reagent can participate in the construction of conjugated polymers or small molecules. The conjugation properties of thiophene groups and the structure formed after the reaction with boric acid can optimize the photoelectric properties of materials. Such as the synthesis of organic Light Emitting Diode (OLED) materials, 4-methylthiophene-3-boronic acid can be synthesized through a precise chemical synthesis path to regulate the key parameters such as the luminous wavelength and efficiency of the material, and contribute to the development of high-performance display materials.
Furthermore, in the field of pesticide chemistry, it is also useful. When synthesizing new pesticide molecules, the special structure of 4-methylthiophene-3-boronic acid can be used to enhance the affinity and activity of pesticides to target organisms. Through rational molecular design and synthesis, integrating it into the molecular structure of pesticides may improve the insecticidal and bactericidal effects of pesticides, while reducing the adverse effects on the environment, and promoting the research and development process of green pesticides.
What is the market price of 4-Methylthiophene-3-boronic acid?
I look at this question and ask about the market price of 4 - Methylthiophene - 3 - boronic acid. However, the market price of this compound is difficult to sum up.
The price of this compound often changes due to many factors. The first to bear the brunt is the production process. If the process is advanced and mature, it can increase the output and reduce the cost, and the price may become easier. On the contrary, the process is complicated and inefficient, the cost will be high, and the price will also be high.
Furthermore, the supply and price of raw materials are also key. If the raw materials are easily available and cheap, the price of the product may be close to the people; if the raw materials are scarce, or the price fluctuates due to external factors, the price of this compound will also be difficult to stabilize.
Market demand also affects its price. If the demand is strong and the supply is limited, the price will rise; if the demand is weak, the merchant will sell it for promotion or reduce its price.
In addition, the manufacturer's brand, Quality Standards, etc. are also affected. Well-known manufacturers, high-standard products, the price may be higher than the average.
Judging from past market conditions, the price of this compound may range from tens to hundreds of yuan per gram. However, this is only a rough number. To know the exact price, you should consult the chemical raw material supplier in detail, or refer to the real-time quotation of the chemical product trading platform to clarify.
What are the storage conditions for 4-Methylthiophene-3-boronic acid?
4-Methylthiophene-3-boronic acid is an important reagent commonly used in organic synthesis. Its chemical properties are active, and it is easy to react with moisture and oxygen in the air, which in turn affects its purity and activity. Therefore, proper preservation of this compound is extremely critical.
Preservation of 4-methylthiophene-3-boronic acid should pay attention to the drying of the environment. Because of its hygroscopicity, it is easy to hydrolyze in contact with water, resulting in structural changes and reduced activity. It should be placed in a dryer. The desiccant can be anhydrous calcium chloride, phosphorus pentoxide, etc., to maintain the drying of the storage environment.
Second, temperature is also an important factor. This compound is more sensitive to temperature, and high temperature is easy to cause it to decompose. Generally speaking, it should be stored in a low temperature environment, preferably 2-8 ° C, such as in a refrigerated refrigerator. Low temperature can slow down its chemical reaction rate and prolong the shelf life.
Furthermore, it is essential to avoid contact with oxygen. 4-Methylthiophene-3-boronic acid can oxidize with oxygen and cause it to deteriorate. Therefore, when storing, it can be filled with inert gases, such as nitrogen, argon, etc., to isolate oxygen.
In addition, the choice of storage containers is also particular. It is advisable to use a sealed container made of glass, because it is chemically stable and does not easily react with compounds. And the sealed container can effectively prevent the intrusion of moisture and oxygen.
In short, in order to properly preserve 4-methylthiophene-3-boronic acid, it is necessary to choose a suitable container in a dry, low temperature and oxygen-isolated environment, so as to ensure its purity and activity, so as to prepare for organic synthesis and other experiments.