2-Chlorothiophene-3-boronic acid

2-Chlorothiophene-3-boronic acid (2-Chlorothiophene-3-boronic acid) is a crucial reagent in the field of organic synthesis and has critical uses in many chemical reactions and product preparation.
First, this reagent is often used in Suzuki-Miyaura coupling reaction. This reaction is an extremely effective method for building carbon-carbon bonds and is widely used in many fields such as pharmaceutical chemistry and materials science. In drug development, with the help of Suzuki-Miyaura coupling reaction, 2-chlorothiophene-3-boronic acid can be coupled with substrates such as halogenated aromatics or olefins to synthesize compounds with complex structures and specific biological activities. In the synthesis of many new anticancer drugs and antibacterial drugs, this reaction is used to build a key molecular skeleton and endow the drug with unique pharmacological activity.
Second, in the field of materials science, this reagent also plays an important role. For example, in the preparation of organic optoelectronic materials, through the Suzuki-Miyaura coupling reaction, 2-chlorothiophene-3-boronic acid can be coupled with other aryl boronic acids or halogenated aromatics to synthesize conjugated polymers with specific optoelectronic properties. These conjugated polymers can be applied to optoelectronic devices such as organic Light Emitting Diode (OLED) and organic solar cells to improve the performance of devices, such as improving the luminous efficiency of OLEDs, prolonging the service life, and enhancing the photoelectric conversion efficiency of organic solar cells.
Third, 2-chlorothiophene-3-boronic acid can also be used to synthesize thiophene derivatives. Thiophene compounds are important intermediates in organic synthesis chemistry because of their unique electronic structure and aromaticity. Through a series of chemical reactions on 2-chlorothiophene-3-boronic acid, such as reacting with nucleophiles and participating in cyclization reactions, various functional thiophene derivatives can be prepared, which are widely used in pesticides, fragrances, dyes and other fields. In the field of pesticides, some thiophene derivatives show good insecticidal and bactericidal activities; in the field of fragrances, some thiophene derivatives have unique aromas and can be used to prepare flavors; in the field of dyes, thiophene derivatives can be used as synthetic raw materials for new dyes, endowing dyes with excellent dyeing properties and stability.

2-Chlorothiophene-3-boronic acid is an important reagent in organic synthesis. It has many physical properties. Looking at its appearance, it is usually a white to off-white solid powder, which is crucial for material identification and preliminary judgment.
In terms of solubility, 2-chlorothiophene-3-boronic acid exhibits specific solubility in common organic solvents. In polar organic solvents such as dichloromethane, N, N-dimethylformamide (DMF), it has a certain solubility, which provides the basis for the selection of reaction solvents in the organic synthesis process. However, in water, its solubility is relatively poor, and this difference is due to the characteristics of functional groups contained in its molecular structure.
In terms of melting point, the melting point of this substance is in a specific range, usually between 120 and 130 ° C. As one of the important physical constants of a substance, the melting point is of great significance for identifying its purity and controlling the reaction process. The higher the purity, the closer the melting point is to the theoretical value, and the narrower the melting range.
Its stability cannot be ignored. Under normal storage conditions, in a dry and cool place, 2-chlorothiophene-3-boronic acid can remain relatively stable. However, it should be noted that it is more sensitive to humidity and air. Exposure to humid air for a long time may cause reactions such as hydrolysis, which may affect its chemical properties and performance.
In summary, the physical properties of 2-chlorothiophene-3-boronic acid, such as appearance, solubility, melting point, and stability, play a decisive role in its application in the field of organic synthesis. Synthesizers need to choose the reaction conditions and storage methods based on these properties to ensure the smooth development of the experiment.

There are several common methods for synthesizing 2-chlorothiophene-3-boronic acid.
First, 2-chlorothiophene is used as the starting material to lithium with butyl lithium. Butyl lithium is strongly basic and can capture hydrogen atoms at specific positions on the thiophene ring to form a lithium compound. This lithium compound reacts with borate esters, such as trimethyl borate or triisopropyl borate. The active carbon-lithium bond of the lithium compound attacks the boron atom of the borate ester nucleophilically, and then hydrolyzes to obtain 2-chlorothiophene-3-boronic acid. In this process, the lithification step needs to be carried out under the harsh conditions of low temperature, anhydrous and oxygen-free. Because butyl lithium is easily reacted with water and oxygen, the reaction yield and product purity are affected.
Second, the coupling reaction strategy catalyzed by transition metals is adopted. 2-chlorothiophene and suitable boron-containing reagents are reacted under the action of transition metal catalysts such as palladium and nickel. For example, using bis (pinacol) diboron as the boron source, the chlorine atom of 2-chlorothiophene is coupled with the boron atom of bis (pinacol) diboron in the presence of palladium catalyst and ligand. The ligand can adjust the electron cloud density and steric resistance of the transition metal catalyst to improve the reaction activity and selectivity. After the reaction, the target product 2-chlorothiophene-3-boronic acid can be separated and purified by appropriate post-treatment, such as column chromatography or recrystallization. This method has relatively mild conditions, slightly lower requirements for reaction equipment, and can better control the reaction selectivity, but the cost of catalysts and ligands is high, or it affects the economy of large-scale preparation.
Or, using thiophene-3-boronic acid as raw material, 2-chlorothiophene-3-boronic acid can be synthesized by chlorination reaction. Select suitable chlorination reagents, such as N-chlorosuccinimide (NCS) or dichlorosulfoxide, etc. Under specific reaction conditions, the chlorine atom of the chlorination reagent replaces the hydrogen atom at the 2-position of the thiophene ring to obtain the target product. The raw materials for this route are relatively easy to obtain, but the regioselectivity of the chlorination reaction needs to be carefully regulated, otherwise a variety of chlorination by-products may be generated, which increases the difficulty of separation and purification.

2-Chlorothiophene-3-boronic acid is an important chemical substance. When storing and transporting, many matters must be paid attention to.
First words storage, this substance should be placed in a cool, dry and well ventilated place. Cover because of its nature or affected by temperature and humidity, if it is placed in a warm and humid place, it may deteriorate. Temperature should be controlled within a specific range. Generally speaking, under normal temperature, it should be prevented from overheating, and it should be protected from direct sunlight. Due to light or chemical reactions.
Furthermore, the storage place should be kept away from fire and heat sources to prevent the risk of fire and explosion. Because of its flammability or easy to react with fire and heat contact. At the same time, it needs to be stored separately from oxidizing agents, acids, alkalis, etc., and cannot be mixed in storage and transportation. Due to its active chemical properties, it encounters with various substances, or reacts violently, damaging its quality, and even leading to safety accidents.
As for transportation, it is necessary to ensure that the packaging is complete and sealed. Packaging materials must have leak-proof and shock-proof effects to ensure that they are not damaged and leaked due to vibration or collision during transportation. During transportation, they should also follow the specified route to avoid densely populated areas and traffic arteries to prevent accidental leakage from endangering the safety of everyone. Transportation vehicles should also be equipped with corresponding fire-fighting equipment and leakage emergency treatment equipment to prepare for emergencies.

The market price of 2-chlorothiophene-3-boronic acid is difficult to determine. This is due to the fickle market conditions, and its price often varies due to many factors.
The first to bear the brunt is the price of raw materials. If the raw materials required for its preparation are scarce or the price is high, the price of 2-chlorothiophene-3-boronic acid will also rise. If the supply of raw materials for preparation is suddenly reduced due to disasters in the place of origin or market monopoly, the price will rise.
Furthermore, the preparation process and cost are also key. Those with complicated processes, huge energy consumption or special equipment and technology will have high costs and high selling prices. If a new process with high efficiency and low cost is developed, the price may drop.
The market supply and demand relationship also affects the price. If the market demand for 2-chlorothiophene-3-boronic acid increases sharply at a certain time, and the supply is limited, the price will rise; on the contrary, if the demand is low and the supply is excessive, the price will decline.
In addition, regional differences also have an impact. Different places have different prices due to different transportation costs, tax policies, and market competition. In prosperous cities or places with concentrated chemical industries, the price may be relatively easy due to intense competition; in remote places, the price may be higher due to the superposition of transportation costs.
According to past market conditions and price trends of similar chemicals, the price of 2-chlorothiophene-3-boronic acid per gram may range from tens to hundreds of yuan. However, this is only a rough estimate. The actual price still needs to be consulted with chemical product suppliers, chemical raw material trading platforms or relevant market practitioners to obtain accurate prices.