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  Vitaly Gurylev,Chung-Yi Su,Tsong-Pyng Perng Phys. Chem. Chem. Phys., 2016,18, 16033-16038
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• Other Chemical Reagents Derivatization Reagents
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Introduction to 2-[4-(bromomethyl)-2-chlorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 1256360-55-0)

2-[4-(Bromomethyl)-2-chlorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 1256360-55-0) is a versatile compound that has gained significant attention in the field of organic synthesis and medicinal chemistry. This compound belongs to the class of boronic esters and is characterized by its unique structural features, including a bromomethyl group and a chlorophenyl moiety. These functionalities make it an attractive building block for various chemical transformations and drug discovery applications.

The bromomethyl group in this compound is particularly noteworthy due to its reactivity in cross-coupling reactions. It can be readily engaged in Suzuki-Miyaura coupling reactions, which are widely used in the synthesis of biologically active molecules. The presence of the chlorophenyl moiety further enhances the compound's utility by providing additional functional groups for further modification and optimization.

In recent years, the development of new synthetic methodologies has significantly expanded the applications of 2-[4-(bromomethyl)-2-chlorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. For instance, a study published in the Journal of Organic Chemistry demonstrated the use of this compound as a key intermediate in the synthesis of novel antiviral agents. The researchers utilized its bromomethyl and chlorophenyl functionalities to construct complex molecular architectures with high efficiency and selectivity.

Another important aspect of this compound is its stability and ease of handling. Unlike some other boronic esters that can be sensitive to air and moisture, 2-[4-(bromomethyl)-2-chlorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane exhibits good stability under standard laboratory conditions. This makes it an ideal choice for large-scale synthesis and industrial applications.

The tetramethyl substituents on the dioxaborolane ring contribute to the overall stability and reactivity of the compound. These substituents help to shield the boron center from unwanted side reactions, thereby enhancing the selectivity of desired transformations. This feature is particularly advantageous in multistep synthetic sequences where high purity and yield are crucial.

In addition to its synthetic applications, 2-[4-(bromomethyl)-2-chlorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane has shown promise in medicinal chemistry research. A recent study published in Bioorganic & Medicinal Chemistry Letters explored its potential as a scaffold for developing new anticancer agents. The researchers found that derivatives of this compound exhibited potent cytotoxic activity against various cancer cell lines. The bromomethyl and chlorophenyl groups were found to play a critical role in modulating the biological activity of these derivatives.

The versatility of 2-[4-(bromomethyl)-2-chlorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane extends beyond its use as a synthetic intermediate. It has also been utilized in polymer chemistry for the preparation of functionalized polymers with controlled architectures. A study published in Macromolecules demonstrated the use of this compound as a chain transfer agent in controlled radical polymerization techniques. The resulting polymers exhibited well-defined molecular weights and narrow polydispersity indices.

The environmental impact of chemical compounds is an increasingly important consideration in modern research and development. In this context, 2-[4-(bromomethyl)-2-chlorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane has been evaluated for its environmental safety. Studies have shown that it can be synthesized using green chemistry principles and that it does not pose significant environmental risks when used under controlled conditions.

In conclusion, 2-[4-(bromomethyl)-2-chlorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 1256360-55-0) is a highly valuable compound with a wide range of applications in organic synthesis, medicinal chemistry, and polymer science. Its unique structural features and excellent reactivity make it an indispensable tool for researchers working on the development of new materials and therapeutic agents.

• 138500-85-3(2-[4-(bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 502630-89-9(1,3,2-Dioxaborolane, 2-(3-chloro-5-methylphenyl)-4,4,5,5-tetramethyl-)
• 870195-94-1(2-(2-Chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 1485110-17-5(2-Chloro-4-hydroxymethylphenylboronic Acid Pinacol Ester)
• 1256781-74-4(2-(2-Chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 957034-64-9(2-Bromomethyl-4-chlorophenylboronic acid, pinacol ester)
• 945391-06-0(3-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile)
• 68716-50-7(2,4-Dichlorophenylboronic acid, pinacol ester)
• 904310-72-1(4-Carboxy-2-chlorophenylboronic acid pinacol ester)
• 1144097-12-0(2-(2-chloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)