1,1'-(1,4-Butanediyl)bis[1,1-dicyclohexylphosphine] tetrafluoroborate(1-) (1:2)
[CAS# 1389309-54-9]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: 1,1'-(1,4-Butanediyl)bis[1,1-dicyclohexylphosphine] tetrafluoroborate(1-) (1:2)
• Synonyms: 1,4-Bis(dicyclohexylphosphonium)butane bis(tetrafluoroborate)
• Molecular Formula: C₂₈H₅₂P₂.2(BF₄).₂H
• Molecular Weight: 626.29
• CAS Registry Number: 1389309-54-9
• EC Number: 842-251-6
• SMILES: [B-](F)(F)(F)F.[B-](F)(F)(F)F.C1CCC(CC1)[PH+](CCCC[PH+](C2CCCCC2)C3CCCCC3)C4CCCCC4

Properties

• Melting point: 236-238 °C

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H314-H318
• Safety Statements: P260-P264-P264+P265-P270-P280-P301+P317-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P330-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1C	H314

Discovery and Applications

1,1'-(1,4-Butanediyl)bis[1,1-dicyclohexylphosphine] tetrafluoroborate(1-) (1:2) is a specialized chemical compound that serves as an effective ligand in various organometallic applications. Known for its unique structure and functional properties, this substance is notable for its use in enhancing catalytic processes.

The discovery of 1,1'-(1,4-Butanediyl)bis[1,1-dicyclohexylphosphine] tetrafluoroborate(1-) can be traced back to the need for highly efficient ligands in metal-catalyzed reactions. The compound features a backbone consisting of a butanediyl bridge linking two 1,1-dicyclohexylphosphine groups, with tetrafluoroborate as the counterion. This specific arrangement imparts significant steric and electronic properties to the ligand, which are advantageous for various chemical processes.

In terms of its application, this ligand is particularly useful in the field of catalytic chemistry. The presence of two 1,1-dicyclohexylphosphine groups provides robust donor properties that enhance the stability of metal complexes. This stability is crucial in facilitating and controlling catalytic reactions, such as cross-coupling reactions, hydrogenations, and other transition metal-catalyzed transformations.

One prominent application of this ligand is in palladium-catalyzed cross-coupling reactions, such as Suzuki-Miyaura or Heck reactions. In these processes, the ligand stabilizes the palladium catalyst, thereby improving its activity and selectivity. The ligand's ability to form strong and stable complexes with palladium makes it an effective choice for achieving high yields and efficient conversions in these reactions.

Additionally, the tetrafluoroborate anion in the compound contributes to its solubility and stability in various solvents, which is beneficial for optimizing reaction conditions. The ligand's electronic properties, influenced by the dicyclohexylphosphine groups and the tetrafluoroborate counterion, help to fine-tune the reactivity of the metal center, making it suitable for a wide range of catalytic applications.

Moreover, the ligand's structure allows for flexibility in its coordination environment, which can be advantageous in developing new catalytic systems and methodologies. Its use extends beyond traditional cross-coupling reactions to include other catalytic processes where enhanced stability and activity of the metal catalyst are required.

In summary, 1,1'-(1,4-Butanediyl)bis[1,1-dicyclohexylphosphine] tetrafluoroborate(1-) represents a valuable tool in organometallic chemistry. Its discovery and subsequent applications highlight its role in improving the efficiency and selectivity of various catalytic reactions. The compound's unique structural features and properties make it a significant ligand for advancing catalytic methodologies and developing new chemical processes.

References

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