Bis[(+)-pinanediolato]diboron
[CAS# 230299-17-9]

Identification

• Classification: Organic raw materials >> Organoboron compounds
• Name: Bis[(+)-pinanediolato]diboron
• Synonyms: Bis[(1S,2S,3R,5S)-pinanediolato]diboron
• Molecular Formula: C₂₀H₃₂B₂O₄
• Molecular Weight: 358.09
• CAS Registry Number: 230299-17-9
• EC Number: 673-660-6
• 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.^*

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
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

Bis[(+)-pinanediolato]diboron is a chemical compound recognized for its distinct structural and functional properties, which contribute to its utility in various fields of chemistry. This compound features two (+)-pinanediol ligands coordinated to a central diboron unit, creating a complex with unique reactivity and applications.

The discovery of bis[(+)-pinanediolato]diboron arose from research focused on enhancing the efficiency and selectivity of boron-based reagents and catalysts. The synthesis of this compound involves reacting diboron with (+)-pinanediol, leading to the formation of a chelated diboron complex. The coordination of the pinanediol ligands to the boron centers stabilizes the complex and influences its reactivity, making it an effective tool in various chemical transformations.

One significant application of bis[(+)-pinanediolato]diboron is in organic synthesis, particularly in cross-coupling reactions such as the Suzuki-Miyaura coupling. This reaction, which forms carbon-carbon bonds between an organoboron compound and an organohalide, is facilitated by the use of bis[(+)-pinanediolato]diboron as a boron source. The compound’s ability to effectively participate in these reactions enhances the synthesis of complex organic molecules, which is valuable in the pharmaceutical industry and the development of advanced materials.

In materials science, bis[(+)-pinanediolato]diboron is utilized in the preparation of boron-containing polymers and materials. The compound can act as a cross-linking agent or a precursor for incorporating boron into polymer matrices. This incorporation can result in materials with improved properties, such as increased thermal stability or enhanced mechanical strength. These properties make it useful in developing high-performance materials for various industrial and technological applications.

The compound also has potential applications in medicinal chemistry. Its boron-containing structure can be employed in the design of novel drugs, where the unique properties of the (+)-pinanediolato ligands may influence the biological activity and selectivity of pharmaceutical agents. Additionally, bis[(+)-pinanediolato]diboron may offer new catalytic pathways or improved selectivity in chemical reactions, contributing to advancements in drug development and chemical synthesis.

Overall, bis[(+)-pinanediolato]diboron is a versatile compound with notable applications in organic synthesis, materials science, and medicinal chemistry. Its unique structure and reactivity make it a valuable reagent and catalyst in advancing various fields of chemical research and industrial applications.

References

2012. Synthesis from Diborane(4) Derivatives and Allylic Alcohols, Acetates, or Carbonates. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-106-00042