Bis[(-)pinanediolato]diboron
[CAS# 230299-05-5]

Identification

• Classification: Organic raw materials >> Organoboron compounds
• Name: Bis[(-)pinanediolato]diboron
• Synonyms: Bis[(1R,2R,3S,5R)-pinanediolato]diboron
• Molecular Formula: C₂₀H₃₂B₂O₄
• Molecular Weight: 358.09
• CAS Registry Number: 230299-05-5
• EC Number: 673-659-0
• SMILES: B1(O[C@@H]2C[C@@H]3C[C@H]([C@@]2(O1)C)C3(C)C)B4O[C@@H]5C[C@@H]6C[C@H]([C@@]5(O4)C)C6(C)C

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 147-151 °C
• alpha: -66 ° (c=6.5, toluene)
• Index of Refraction: 1.517, Calc.^*
• Boiling Point: 360.6±9.0 °C (760 mmHg), Calc.^*
• Flash Point: 171.9±18.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

Bis[(-)-pinanediolato]diboron is a notable chemical compound with unique structural and functional characteristics that have led to its application in various fields of chemistry and materials science. This compound is distinguished by its use of (-)-pinanediol as a ligand in a diboron complex, providing distinctive properties that enhance its utility in chemical reactions and material synthesis.

The discovery of bis[(-)-pinanediolato]diboron can be attributed to ongoing research in the development of boron-based reagents and catalysts. The compound is synthesized through the reaction of diboron with (-)-pinanediol, resulting in the formation of a diboron complex where the pinanediol ligands are chelated to the boron atoms. This chelation is facilitated by the coordination of the diol groups to the boron centers, stabilizing the complex and imparting specific reactivity profiles.

One of the primary applications of bis[(-)-pinanediolato]diboron is in organic synthesis, particularly in the field of cross-coupling reactions. The compound serves as a boron source in Suzuki-Miyaura coupling reactions, where it acts as a reagent to facilitate the formation of carbon-carbon bonds. Its effectiveness in these reactions is due to the stability and reactivity of the boron complex, which enables efficient coupling with various organic substrates. The use of this compound in such reactions allows for the synthesis of complex organic molecules, which is valuable in the development of pharmaceuticals and advanced materials.

In materials science, bis[(-)-pinanediolato]diboron is utilized in the preparation of boron-containing polymers and materials. The compound's ability to act as a cross-linking agent or as a precursor for the incorporation of boron into polymer matrices makes it useful in developing materials with enhanced properties, such as increased thermal stability or improved mechanical strength. Its role in polymer chemistry contributes to advancements in material design, particularly in the creation of high-performance materials for industrial and technological applications.

Furthermore, the compound has potential applications in medicinal chemistry and catalysis. Its boron-containing structure can influence the biological activity of compounds when used as a building block in drug design. Additionally, the unique properties of the pinanediolato ligands may offer new catalytic pathways or improved selectivity in chemical reactions.

Overall, bis[(-)-pinanediolato]diboron is a versatile compound with significant applications in organic synthesis, materials science, and potentially medicinal chemistry. Its distinctive structural features and reactivity make it a valuable tool for advancing various fields of chemical research and industrial applications.

References

2020. Synthesis of Taniborbactam. Synfacts, 16(03).
DOI: 10.1055/s-0039-1691689

2018. Recent Developments and Applications of the Chiral Brønsted Acid Catalyzed Allylboration of Carbonyl Compounds. Synthesis, 50(08).
DOI: 10.1055/s-0036-1589532