(Diphenylphosphine)borane
[CAS# 41593-58-2]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: (Diphenylphosphine)borane
• Synonyms: (Diphenylphosphine)trihydroboron; (T-4)-(Diphenylphosphine)trihydroboron
• Molecular Formula: C₁₂H₁₁P.BH₃
• Molecular Weight: 200.03
• CAS Registry Number: 41593-58-2
• EC Number: 627-404-5
• SMILES: [B].C1=CC=C(C=C1)PC2=CC=CC=C2

Properties

• Melting point: 42-47 °C

Safety Data

• Hazard Symbols: GHS02 Danger
• Risk Statements: H261
• Safety Statements: P231+P232-P280-P370+P378-P402+P404-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Substances or mixtures which in contact with water emit flammable gases	Water-react.	2	H261

Discovery and Applications

(Diphenylphosphine)borane, a compound characterized by the presence of a borane group attached to a diphenylphosphine moiety, represents an important class of organophosphorus compounds with distinctive properties and applications in chemistry. This substance combines the reactivity of phosphines with the unique features of borane groups, making it a valuable tool in various chemical processes.

The discovery of (diphenylphosphine)borane emerged from efforts to develop new phosphine-borane adducts with tailored electronic and steric properties. The synthesis of this compound involves the reaction between diphenylphosphine and borane (BH3), often facilitated by appropriate solvents and reaction conditions to achieve the desired product. The resulting adduct is typically characterized by techniques such as nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and mass spectrometry, which confirm its structure and purity.

The primary application of (diphenylphosphine)borane is in the field of organometallic chemistry, particularly as a ligand in various catalytic processes. The compound's ability to stabilize metal centers through coordination with the phosphorus atom enhances the performance of metal catalysts in a range of chemical reactions. This includes applications in hydrogenation, hydroformylation, and other metal-catalyzed transformations where the phosphine-borane adduct plays a crucial role in modulating the reactivity and selectivity of the metal center.

In addition to its use as a ligand, (diphenylphosphine)borane serves as a reducing agent in certain chemical reactions. The borane group is known for its strong reducing properties, which can be leveraged in reduction reactions involving various substrates. This application is particularly valuable in organic synthesis, where selective reduction of functional groups is often required.

The compound also finds application in the development of new materials. The unique electronic properties imparted by the borane group, combined with the steric effects of the diphenylphosphine moiety, make (diphenylphosphine)borane useful in creating materials with specific properties. These materials can be utilized in various fields, including catalysis, materials science, and electronics.

Handling and storage of (diphenylphosphine)borane require careful consideration due to the reactivity of both the phosphine and borane groups. The compound should be stored in an inert atmosphere to prevent decomposition or reaction with moisture and air. Additionally, proper safety precautions should be taken during its use in laboratory and industrial settings.

Future research on (diphenylphosphine)borane may focus on exploring new applications and optimizing its performance in various catalytic and synthetic processes. The development of new derivatives and modifications of the phosphine and borane groups could further enhance the utility of this compound in diverse chemical contexts.

References

2002. Parallel Catalytic Synthesis of Phosphines and Related Ligands. Principles and Methods for Accelerated Catalyst Design and Testing.
DOI: 10.1007/978-94-010-0554-8_14


2014. Recent Advances in Synthesis of P-BH3 Compounds. Topics in Current Chemistry, 360.
DOI: 10.1007/128_2014_565