Bis(pinacolato)diboron, with the CAS number 73183-34-3, is a significant organoboron compound. It has a molecular formula of C12H24B2O4 and a molecular weight of approximately 253.94 g/mol. The compound appears as a white to off - white crystalline powder. It is known for its high purity when obtained from reliable factory supplies. Its melting point ranges from 135 - 140 °C, which is an important parameter for handling and storage. The solubility of bis(pinacolato)diboron is notable in common organic solvents such as toluene, dichloromethane, and tetrahydrofuran (THF), but it is insoluble in water. This solubility property makes it convenient for various chemical reactions carried out in organic media.
Bis(pinacolato)diboron finds extensive applications in the field of organic synthesis. One of its primary uses is in the Suzuki - Miyaura cross - coupling reaction. In this reaction, it serves as a boron source to introduce boron moieties into organic molecules. This is crucial for the construction of carbon - carbon bonds, which are fundamental in the synthesis of complex organic compounds, such as pharmaceuticals, agrochemicals, and advanced materials. For example, in the pharmaceutical industry, it can be used to synthesize new drug candidates with specific structures and functions. Additionally, it is used in the preparation of boron - containing polymers, which have unique properties such as good thermal stability and electrical conductivity. These polymers can be applied in the fields of electronics and materials science.
When using bis(pinacolato)diboron, it is essential to handle it under appropriate laboratory conditions. First, ensure that all equipment is clean and dry to prevent side reactions caused by moisture. Since it is sensitive to air and moisture, it should be stored in a sealed container under an inert atmosphere, such as nitrogen or argon. In a typical reaction, an appropriate amount of bis(pinacolato)diboron is weighed and added to the reaction mixture. The choice of solvent depends on the specific reaction requirements. For example, in a Suzuki - Miyaura coupling reaction, THF or toluene is often used. The reaction usually requires a catalyst, such as a palladium - based catalyst, and a base. The reaction temperature and time also need to be carefully controlled according to the reaction mechanism and the nature of the reactants. After the reaction is completed, the product can be purified by standard purification methods, such as column chromatography or recrystallization.
Case 1: Pharmaceutical Synthesis
A research group was working on the synthesis of a new anti - cancer drug. They used bis(pinacolato)diboron in a Suzuki - Miyaura cross - coupling reaction. The starting aryl halide was reacted with bis(pinacolato)diboron in the presence of a palladium catalyst and a base in THF. By carefully controlling the reaction conditions, they were able to obtain a boron - containing intermediate with high yield. This intermediate was then further transformed into the final anti - cancer drug. The use of bis(pinacolato)diboron in this process simplified the synthesis route and improved the overall efficiency of the drug synthesis.
Case 2: Material Science
In the development of new conductive polymers, bis(pinacolato)diboron was used to introduce boron units into the polymer backbone. The reaction was carried out in a toluene solution with a specific catalyst system. The resulting boron - containing polymer showed improved electrical conductivity compared to traditional polymers. This new polymer has potential applications in the manufacturing of flexible electronic devices, such as organic light - emitting diodes (OLEDs) and solar cells.
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