Bis(hexylene glycolato)diboron
[CAS# 230299-21-5]

Identification

• Classification: Organic raw materials >> Organoboron compounds
• Name: Bis(hexylene glycolato)diboron
• Synonyms: Bis(diisopropyl-L-tartrate glycolato)diboron
• Molecular Formula: C₁₂H₂₄B₂O₄
• Molecular Weight: 253.94
• CAS Registry Number: 230299-21-5
• EC Number: 673-658-5
• SMILES: B1(OC(CC(O1)(C)C)C)B2OC(CC(O2)(C)C)C

Properties

• Melting point: 98-102 ºC
• Water solubility: Insoluble

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

Bis(hexylene glycolato)diboron is a notable chemical compound in the field of organoboron chemistry, distinguished by its structural configuration and diverse applications. This compound consists of a diboron core coordinated by two hexylene glycolate ligands, creating a stable and reactive complex with significant utility in various chemical processes.

The discovery of bis(hexylene glycolato)diboron emerged from research aimed at developing versatile boron-containing reagents and catalysts. The synthesis of this compound involves the reaction of diboron with hexylene glycol, resulting in a diboron complex where the hexylene glycolate ligands coordinate to the boron centers. This chelation stabilizes the boron atoms and imparts specific chemical properties to the compound, making it a valuable tool in synthetic chemistry.

One of the primary applications of bis(hexylene glycolato)diboron is in organic synthesis, particularly in cross-coupling reactions such as the Suzuki-Miyaura coupling. In this reaction, bis(hexylene glycolato)diboron serves as a boron reagent that facilitates the formation of carbon-carbon bonds between an organoboron compound and an organohalide. This capability enhances the synthesis of complex organic molecules, which is particularly useful in the pharmaceutical industry and in the development of new materials.

In addition to its role in organic synthesis, bis(hexylene glycolato)diboron is utilized in materials science. The compound can be employed in the preparation of boron-containing polymers and materials, where it acts as a cross-linking agent or a precursor for incorporating boron into polymer matrices. This incorporation can lead to the development of materials with improved properties, such as increased thermal stability or enhanced mechanical strength, making it useful for various industrial and technological applications.

Furthermore, bis(hexylene glycolato)diboron has potential applications in catalytic processes. The unique properties of the hexylene glycolate ligands can influence the catalytic behavior of the boron complex, providing new pathways or enhancing selectivity in chemical reactions. This aspect of the compound contributes to advancements in catalytic chemistry and the development of more efficient and selective catalytic systems.

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