Trimethylboroxin, uniquely identified by its Chemical Abstracts Service (CAS) number 823-96-1, stands as a highly versatile and increasingly vital compound within the realm of organic chemistry and beyond. This colorless liquid is recognized for its unique chemical structure, a six-membered ring comprising alternating oxygen and boron atoms, each bonded to a methyl group.

Key physical and chemical properties define Trimethylboroxin's utility. It possesses a molecular formula of C3H9B3O3 and a molecular weight of 125.535 g/mol. Characteristically, it has a low melting point of approximately -38 °C and a boiling point near 79 °C at standard atmospheric pressure. Its density is around 0.9 g/cm3, and it exhibits high purity, typically at 99% minimum, which is crucial for its precise applications in sensitive chemical processes. Furthermore, Trimethylboroxin demonstrates remarkable stability, facilitating long-term storage and consistent performance.

The applications of Trimethylboroxin are diverse and significant. Primarily, it functions as a critical organic intermediate in complex synthetic pathways. Its ability to act as a universal methylating reagent has made it indispensable in C-H methylation reactions, enabling chemists to introduce methyl groups into various organic molecules with high efficiency. This capability is vital for the synthesis of pharmaceuticals, agrochemicals, and specialty materials.

Beyond its role as a reagent, Trimethylboroxin also serves as an effective catalyst in selected chemical reactions, accelerating reaction rates and improving yields. Its electronic properties, particularly its robust electron-accepting nature, allow it to participate in electron transfer processes, making it valuable in both chemical and biochemical research settings. Recent research highlights its increasing importance in cutting-edge fields. For instance, it has shown considerable promise as an electrolyte additive for advanced lithium-ion batteries. Studies have indicated that incorporating Trimethylboroxin can significantly enhance the cyclic stability and high-voltage performance of critical cathode materials, such as lithium cobalt oxide and layered lithium nickel cobalt manganese oxide, paving the way for more durable and efficient energy storage solutions.

Additional specialized applications include its use in palladium-catalyzed nucleomethylation of alkynes for synthesizing methylated heteroaromatic compounds, and in rhodium/chiral diene-catalyzed asymmetric methylation of N-sulfonylarylimines. These sophisticated applications underscore the compound's precision and efficacy in advanced synthetic methodologies, broadening its appeal across various scientific disciplines.

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While Trimethylboroxin is an invaluable chemical, it is important to note its hazard classifications. It is identified as a highly flammable liquid and vapor, an irritant to skin, eyes, and the respiratory system, and may form explosive peroxides. Proper handling, storage in a designated flammables area, and the use of appropriate personal protective equipment are essential. Always refer to the Safety Data Sheet (SDS) for comprehensive safety guidelines.

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