Bis(2,4-dimethylpentane-2,4-glycolato)diboron
[CAS# 230299-46-4]

Identification

• Classification: Organic raw materials >> Organoboron compounds
• Name: Bis(2,4-dimethylpentane-2,4-glycolato)diboron
• Synonyms: 4,4,6,6-tetramethyl-2-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-1,3,2-dioxaborinane
• Molecular Formula: C₁₄H₂₈B₂O₄
• Molecular Weight: 281.99
• CAS Registry Number: 230299-46-4
• SMILES: B1(OC(CC(O1)(C)C)(C)C)B2OC(CC(O2)(C)C)(C)C

Properties

• Melting point: 58-70 °C
• Boiling Point: 255 °C (760 mmHg)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

Bis(2,4-dimethylpentane-2,4-glycolato)diboron is a significant compound in the realm of organoboron chemistry, noted for its distinct structure and versatile applications. This compound features a central diboron unit coordinated by two 2,4-dimethylpentane-2,4-glycolate ligands. The resulting complex exhibits unique properties that make it valuable in various chemical processes.

The discovery of bis(2,4-dimethylpentane-2,4-glycolato)diboron stemmed from research focused on developing more effective boron-based reagents and catalysts. The synthesis of this compound involves reacting diboron with 2,4-dimethylpentane-2,4-diol, leading to the formation of a diboron complex where the glycolate ligands stabilize the boron centers. This configuration enhances the reactivity and stability of the compound, making it suitable for a range of applications.

In organic synthesis, bis(2,4-dimethylpentane-2,4-glycolato)diboron is particularly valuable in cross-coupling reactions, such as the Suzuki-Miyaura coupling. In this reaction, the compound acts as a boron source, facilitating the formation of carbon-carbon bonds between an organoboron compound and an organohalide. This ability significantly aids the synthesis of complex organic molecules, which is crucial for pharmaceutical development and the creation of advanced materials.

The compound also finds applications in materials science. Bis(2,4-dimethylpentane-2,4-glycolato)diboron can be used in the preparation of boron-containing polymers and materials. It functions as a cross-linking agent or a precursor for incorporating boron into polymer matrices, leading to the development of materials with enhanced properties such as improved thermal stability or increased mechanical strength. These advancements are valuable for various industrial and technological applications.

Moreover, bis(2,4-dimethylpentane-2,4-glycolato)diboron is explored for its catalytic properties. The unique characteristics of the 2,4-dimethylpentane-2,4-glycolate ligands can influence the catalytic behavior of the boron complex, offering new pathways or improving selectivity in chemical reactions. This aspect contributes to advancements in catalytic chemistry, facilitating more efficient and selective catalytic processes.

Overall, bis(2,4-dimethylpentane-2,4-glycolato)diboron is a versatile compound with important roles in organic synthesis, materials science, and catalytic chemistry. Its unique structural features and reactivity make it a valuable reagent and catalyst, driving progress in various fields of chemical research and industrial applications.

References

2020. ANIPE-Cu Catalyst Enables Highly Enantioselective Markovnikov Hydroboration of α-Olefins. Synlett, 31(18).
DOI: 10.1055/a-1288-2990

2018. Recent Advances in Copper-Catalyzed Asymmetric Hydroboration of Electron-Deficient Alkenes: Methodologies and Mechanism. Synthesis, 50(14).
DOI: 10.1055/s-0037-1609583

2019. Asymmetric Hydroboration. Science of Synthesis.
URL: SD-230-00250