1,3-Bis(dicyclohexylphosphonium)propane bis(tetrafluoroborate)
[CAS# 1002345-50-7]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: 1,3-Bis(dicyclohexylphosphonium)propane bis(tetrafluoroborate)
• Molecular Formula: C₂₇H₅₀P₂.2(BF₄).₂H
• Molecular Weight: 612.26
• CAS Registry Number: 1002345-50-7
• EC Number: 635-571-0
• SMILES: [B-](F)(F)(F)F.[B-](F)(F)(F)F.C1CCC(CC1)[PH+](CCC[PH+](C2CCCCC2)C3CCCCC3)C4CCCCC4

Properties

• Melting point: 154-155 °C^*

^* Martinelli, Joeseph R.

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
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Skin corrosion	Skin Corr.	1C	H314
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

1,3-Bis(dicyclohexylphosphonium)propane bis(tetrafluoroborate) is a noteworthy compound in the realm of organic chemistry and catalysis. This compound, also known as a dicationic phosphonium salt, has garnered attention for its role in various catalytic processes, particularly in transition metal-catalyzed reactions. Its discovery and subsequent applications have provided chemists with a versatile tool for enhancing reaction efficiency and selectivity.

The compound consists of a propane backbone with two dicyclohexylphosphonium groups attached at the 1 and 3 positions. These positively charged phosphonium groups are balanced by two tetrafluoroborate anions, resulting in a stable salt. The presence of the bulky dicyclohexyl groups imparts significant steric hindrance, which can influence the reactivity and selectivity of the catalytic processes in which it is employed.

The discovery of 1,3-Bis(dicyclohexylphosphonium)propane bis(tetrafluoroborate) was driven by the need for highly effective and selective catalysts in organic synthesis. Researchers exploring new avenues in organophosphorus chemistry identified the potential of dicationic phosphonium salts to serve as ligands and stabilizers in various catalytic systems. This led to the synthesis and subsequent investigation of the compound's properties and applications.

One of the most significant applications of 1,3-Bis(dicyclohexylphosphonium)propane bis(tetrafluoroborate) is in transition metal-catalyzed cross-coupling reactions. These reactions, essential for forming carbon-carbon and carbon-heteroatom bonds, are foundational in the synthesis of pharmaceuticals, agrochemicals, and complex organic molecules. The compound's ability to stabilize reactive intermediates and enhance the activity of transition metal catalysts has made it a valuable additive in these processes.

Additionally, the compound has been employed in the development of novel catalytic systems for olefin metathesis and polymerization reactions. Its unique steric and electronic properties can modulate the behavior of metal catalysts, leading to improved yields and selectivities in these reactions. As a result, it has become an important tool in both academic research and industrial applications.

Beyond its use in catalysis, 1,3-Bis(dicyclohexylphosphonium)propane bis(tetrafluoroborate) has also been explored for its potential in materials science. Its ionic nature and the presence of bulky phosphonium groups make it a candidate for the design of ionic liquids and other functional materials with specialized properties, such as enhanced conductivity or thermal stability.

In summary, 1,3-Bis(dicyclohexylphosphonium)propane bis(tetrafluoroborate) is a compound of significant interest due to its role in catalysis and potential applications in materials science. Its discovery has enabled the development of more efficient and selective catalytic processes, contributing to advances in organic synthesis and beyond.

References

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