4-Hydroxyphenylboronic acid pinacol ester CAS: 269409-70-3
Catalog Number | XD93454 |
Product Name | 4-Hydroxyphenylboronic acid pinacol ester |
CAS | 269409-70-3 |
Molecular Formula | C12H17BO3 |
Molecular Weight | 220.07 |
Storage Details | Ambient |
Product Specification
Appearance | White powder |
Assay | 99% min |
4-Hydroxyphenylboronic acid pinacol ester, also known as HBP ester, is a chemical compound that finds applications in various fields due to its unique properties as a boronic ester. Its chemical structure consists of a boron atom attached to a phenolic group via an ester linkage, making it a valuable building block for organic synthesis.In organic synthesis, 4-Hydroxyphenylboronic acid pinacol ester is commonly used as a reagent for the Suzuki-Miyaura cross-coupling reaction. This reaction involves the formation of a carbon-carbon bond between an aryl or vinyl boronic acid and an aryl or vinyl halide or triflate. As a boronic ester, HBP ester acts as a precursor to the corresponding boronic acid, which can undergo the cross-coupling reaction with various electrophiles, leading to the formation of complex organic molecules. This reaction has significant applications in medicinal chemistry, agrochemical synthesis, material science, and many other areas of organic synthesis.The versatility of HBP ester lies in its ability to undergo functional group transformations, such as oxidation or reduction, to introduce additional functionality into the molecule. For example, the hydroxyl group of the phenolic moiety can be protected and later deprotected, allowing for selective modification and diversification of the compound. This property makes HBP ester a valuable tool in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals.Furthermore, HBP ester is often used in the construction of molecular sensors and probes. Due to the boron atom in its structure, it can form reversible complexes with diols or polyols, such as sugars or carbohydrates. This property enables the development of boronate-based sensors for the detection of glucose, as well as other biologically relevant molecules. HBP ester can be incorporated into various sensing platforms, including fluorescent or colorimetric probes, providing a means to detect specific analytes in biological or environmental samples.Apart from its use in organic synthesis and sensing applications, 4-Hydroxyphenylboronic acid pinacol ester has also been investigated for its potential role in drug delivery systems. The boron atom can participate in interactions with biomolecules, such as nucleic acids or proteins, and has been explored for targeted drug delivery, enhanced cellular uptake, or controlled release of therapeutic agents.In summary, 4-Hydroxyphenylboronic acid pinacol ester is a versatile compound used in organic synthesis, sensing applications, and drug delivery systems. Its boronic ester functionality enables it to participate in the Suzuki-Miyaura cross-coupling reaction and undergo functional group transformations, expanding its synthetic utility. Additionally, HBP ester can form reversible complexes with diols, making it valuable for the development of molecular sensors. Its potential in drug delivery systems further underscores its importance as a versatile compound in various scientific and technological fields.