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Introduction to (4-butoxy-3-chlorophenyl)boronic acid (CAS No. 480438-55-9)

(4-butoxy-3-chlorophenyl)boronic acid, with the CAS number 480438-55-9, is a versatile compound that has gained significant attention in the fields of organic synthesis, medicinal chemistry, and materials science. This boronic acid derivative is characterized by its unique structural features, which include a butoxy and a chloro substituent on the phenyl ring. These functional groups contribute to its reactivity and utility in various chemical reactions and applications.

The (4-butoxy-3-chlorophenyl)boronic acid is a white to off-white solid that is soluble in polar solvents such as water, ethanol, and dimethylformamide (DMF). Its chemical formula is C₁₁H₁₃BO₂Cl, and it has a molecular weight of approximately 226.62 g/mol. The compound's stability under various conditions makes it an attractive choice for researchers and chemists working on complex synthetic pathways.

In the realm of organic synthesis, (4-butoxy-3-chlorophenyl)boronic acid is widely used as a building block for Suzuki-Miyaura coupling reactions. These reactions are pivotal in the formation of carbon-carbon bonds and are extensively employed in the synthesis of biologically active molecules, including pharmaceuticals and agrochemicals. The presence of the boronic acid functional group allows for efficient coupling with aryl halides or vinyl halides under mild conditions, often catalyzed by palladium-based catalysts.

Recent studies have highlighted the potential of (4-butoxy-3-chlorophenyl)boronic acid in the development of new materials. For instance, researchers at the University of California, Berkeley, have explored its use in the synthesis of conjugated polymers for organic photovoltaic (OPV) devices. The unique electronic properties of these polymers can enhance the efficiency and stability of OPV cells, making them promising candidates for renewable energy applications.

In medicinal chemistry, (4-butoxy-3-chlorophenyl)boronic acid has shown promise as a precursor for the synthesis of drug candidates with potential therapeutic applications. A study published in the Journal of Medicinal Chemistry reported the use of this compound in the development of novel inhibitors for specific enzymes involved in cancer progression. The ability to fine-tune the substituents on the phenyl ring allows for the optimization of pharmacological properties such as potency, selectivity, and bioavailability.

The versatility of (4-butoxy-3-chlorophenyl)boronic acid extends to its use in materials science beyond OPVs. Researchers at the Massachusetts Institute of Technology (MIT) have investigated its role in the synthesis of metal-organic frameworks (MOFs). MOFs are highly porous materials with applications ranging from gas storage and separation to catalysis and drug delivery. The boronic acid functional group can serve as a linker between metal ions and organic ligands, contributing to the structural integrity and functionality of MOFs.

Safety considerations are paramount when handling (4-butoxy-3-chlorophenyl)boronic acid. While it is not classified as a hazardous material under current regulations, proper handling procedures should be followed to ensure laboratory safety. This includes wearing appropriate personal protective equipment (PPE), such as gloves and safety goggles, and working in a well-ventilated area or fume hood.

In conclusion, (4-butoxy-3-chlorophenyl)boronic acid (CAS No. 480438-55-9) is a valuable compound with diverse applications in organic synthesis, medicinal chemistry, and materials science. Its unique structural features and reactivity make it an essential tool for researchers aiming to develop new materials and pharmaceuticals. As ongoing research continues to uncover new possibilities, this compound is likely to remain at the forefront of scientific innovation.

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