Dicyclohexylphosphine-borane
[CAS# 108756-88-3]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Dicyclohexylphosphine-borane
• Synonyms: (Dicyclohexylphosphine)trihydroboron
• Molecular Formula: C₁₂H₂₃P.BH₃
• Molecular Weight: 212.12
• CAS Registry Number: 108756-88-3
• SMILES: [B].C1CCC(CC1)PC2CCCCC2

Properties

• Melting point: 80-81 °C

Safety Data

• Hazard Symbols: GHS02 Danger

Discovery and Applications

Dicyclohexylphosphine-borane, a versatile chemical compound, plays a significant role in modern chemistry due to its unique properties and applications. This compound, with the chemical formula [(C₆H₁₁)₂PH]·BH₃, combines a dicyclohexylphosphine moiety with a borane group. The phosphine-borane complex is particularly noteworthy for its utility in organic synthesis and catalysis.

The discovery of dicyclohexylphosphine-borane emerged from efforts to create stable and effective phosphine-borane complexes. Phosphine-borane complexes are known for their ability to stabilize reactive intermediates and facilitate various chemical transformations. Dicyclohexylphosphine-borane, in particular, benefits from the steric and electronic properties imparted by the dicyclohexyl groups, which enhance its stability and reactivity.

One of the primary applications of dicyclohexylphosphine-borane is in the field of catalysis. In organic synthesis, this compound is used as a reducing agent and a ligand in transition metal-catalyzed reactions. The borane component is a strong reducing agent, making dicyclohexylphosphine-borane effective in reducing various functional groups, including carbonyls and imines. This reduction capability is valuable in the synthesis of a wide range of organic compounds, including pharmaceuticals and fine chemicals.

Dicyclohexylphosphine-borane is also employed as a stabilizing agent for reactive intermediates in catalytic processes. Its ability to stabilize transition states and reactive species allows for smoother and more controlled chemical reactions. In particular, it is used in hydroboration reactions, where it facilitates the addition of boron-hydrogen (B-H) bonds to alkenes and alkynes. This application is crucial in the formation of organoboron compounds, which are important in further synthetic transformations and material science.

Additionally, the compound serves as a precursor in the synthesis of other phosphine-borane complexes and organophosphorus compounds. Its stable nature and reactivity make it an ideal starting material for creating new ligands and catalysts. The versatility of dicyclohexylphosphine-borane in forming various derivatives expands its utility in both academic research and industrial applications.

Overall, dicyclohexylphosphine-borane is a valuable chemical substance with significant applications in synthesis and catalysis. Its discovery has provided chemists with an effective tool for reducing and stabilizing reactive intermediates, facilitating a wide range of chemical transformations. As research continues, the compound's role in advancing chemical synthesis and catalysis is expected to grow, further highlighting its importance in the field of chemistry.

References

2014. Recent Advances in Synthesis of P-BH3 Compounds. Topics in Current Chemistry.
DOI: 10.1007/128_2014_565

2009. Synthesis from Dialkylphosphides or Dialkylphosphines and Dialkylhalophosphines. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-042-00143