Potassium trifluoro((5-fluoro-2-methoxybenzamido)methyl)borate
[CAS# 2089246-64-8]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: Potassium trifluoro((5-fluoro-2-methoxybenzamido)methyl)borate
• Molecular Formula: C₉H₉BF₄KNO₂
• Molecular Weight: 289.08
• CAS Registry Number: 2089246-64-8
• SMILES: [B-](CNC(=O)C1=C(C=CC(=C1)F)OC)(F)(F)F.[K+]

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovery and Applications

Potassium trifluoro((5-fluoro-2-methoxybenzamido)methyl)borate belongs to a class of organoboron compounds known as potassium organotrifluoroborates. These compounds have attracted considerable interest in modern organic chemistry because of their stability, ease of handling, and usefulness as reagents in carbon–carbon and carbon–heteroatom bond forming reactions. The development of organotrifluoroborates represented an important advance in boron chemistry, providing stable alternatives to many traditional organoboron reagents that were often sensitive to air and moisture. Research into organoboron chemistry dates back to the early twentieth century, but the major expansion of the field occurred after the development of new methods for forming carbon–boron bonds and their application in cross-coupling reactions. Organoboronic acids and esters became widely used intermediates because they could participate in metal-catalyzed coupling reactions to form carbon–carbon bonds. However, many of these compounds exhibited limited stability during storage and handling. To address these limitations, chemists developed organotrifluoroborate salts, which contain a tetrahedral boron center bound to three fluorine atoms and an organic substituent. These salts are generally crystalline, stable under ambient conditions, and often more convenient to use than the corresponding boronic acids. Potassium trifluoro((5-fluoro-2-methoxybenzamido)methyl)borate represents a specialized derivative within this family. In this compound, the boron atom is bonded to a substituted benzamido methyl group that contains both fluorine and methoxy substituents on the aromatic ring. Such structural features are commonly introduced to influence electronic properties and reactivity during synthetic transformations. The presence of the amide functionality in the substituent also allows participation in hydrogen bonding and coordination interactions, which can affect the behavior of the molecule in chemical reactions. Compounds of this type are typically prepared through conversion of corresponding boronic acids or boronate esters into the trifluoroborate form using fluoride sources in the presence of potassium ions. The resulting potassium organotrifluoroborate salts are usually isolated as stable solids that can be stored for extended periods without significant decomposition. Their improved stability compared with many boronic acids has made them attractive reagents for use in laboratory and industrial synthetic processes. One of the most important applications of organotrifluoroborates is their use in transition-metal-catalyzed cross-coupling reactions. In these reactions, the carbon group attached to boron can be transferred to another molecule under the influence of a metal catalyst. This transformation allows chemists to construct new carbon–carbon bonds with high selectivity and efficiency. Organotrifluoroborates can serve as effective coupling partners in these reactions, often showing improved tolerance to moisture and air compared with other boron reagents. Because of these properties, they have become widely used intermediates in the synthesis of complex organic molecules. Another area in which such compounds have been used is medicinal chemistry. Many pharmaceutical research programs rely on efficient synthetic methods to construct aromatic and heteroaromatic frameworks containing specific substituents. Organotrifluoroborates that incorporate functional groups such as amides, halogens, or methoxy substituents can serve as building blocks for preparing molecules with desired structural features. The ability to incorporate substituted aromatic groups through cross-coupling reactions has made these reagents valuable tools in the preparation of compounds for biological testing. In addition to their use in carbon–carbon bond formation, organotrifluoroborates have also been applied in reactions that create carbon–heteroatom bonds. These transformations enable the introduction of nitrogen, oxygen, or other heteroatoms into organic frameworks. The versatility of the boron–carbon bond in these reagents has therefore contributed to the development of a wide range of synthetic methodologies used in research laboratories. The combination of stability, reactivity, and functional group compatibility has made potassium organotrifluoroborates important intermediates in contemporary synthetic chemistry. Potassium trifluoro((5-fluoro-2-methoxybenzamido)methyl)borate represents one example of a functionalized member of this class. Through participation in cross-coupling and related reactions, compounds of this type support the efficient construction of complex molecules used in chemical research, pharmaceutical development, and other areas of applied organic chemistry.

References

2025. Pirtobrutinib. Pharmaceutical Substances.