Bis(1,1-dimethylethyl)(methyl)phosphine tetrafluoroborate
[CAS# 479094-62-7]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Bis(1,1-dimethylethyl)(methyl)phosphine tetrafluoroborate
• Synonyms: Di-tert-butyl(methyl)phosphonium tetrafluoroborate
• Molecular Formula: C₉H₂₁P^.BF₄^.H
• Molecular Weight: 248.05
• CAS Registry Number: 479094-62-7
• EC Number: 808-098-4
• SMILES: [B-](F)(F)(F)F.CC(C)(C)[PH+](C)C(C)(C)C

Properties

• Melting point: >230 ºC

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H314-H315-H319-H335
• Precautionary Statements: P260-P261-P264-P264+P265-P271-P280-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P319-P321-P332+P317-P337+P317-P362+P364-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin corrosion	Skin Corr.	1C	H314
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

Bis(1,1-dimethylethyl)(methyl)phosphine tetrafluoroborate is a specialized chemical compound in the field of organophosphorus chemistry, known for its role as a ligand in various catalytic applications. This substance, with the molecular formula C10H16BF4P, is notable for its unique properties imparted by the bulky tert-butyl groups attached to the phosphine moiety.

The discovery of Bis(1,1-dimethylethyl)(methyl)phosphine tetrafluoroborate originated from research aimed at developing new phosphine ligands with enhanced steric and electronic properties. The synthesis of this compound involves the reaction of 1,1-dimethylethyl(methyl)phosphine with a suitable fluoroborate salt. This process is typically carried out under controlled conditions to ensure the formation of the tetrafluoroborate salt, which stabilizes the phosphine ligand.

In terms of its structure, Bis(1,1-dimethylethyl)(methyl)phosphine tetrafluoroborate features a phosphine center bonded to two tert-butyl groups and one methyl group, with the tetrafluoroborate anion providing charge balance. The bulky tert-butyl groups enhance the steric properties of the ligand, making it particularly useful in stabilizing metal centers in various catalytic reactions.

The primary application of Bis(1,1-dimethylethyl)(methyl)phosphine tetrafluoroborate is as a ligand in metal-catalyzed processes. The steric hindrance provided by the tert-butyl groups contributes to the effectiveness of the ligand in stabilizing metal complexes, which are essential for catalytic transformations. This ligand is used in various reactions, including cross-coupling processes and hydrogenation, where it helps to improve the efficiency and selectivity of the metal catalysts.

One significant application of this ligand is in the field of homogeneous catalysis, where it is used to facilitate the formation of complex organic molecules. The steric and electronic properties of Bis(1,1-dimethylethyl)(methyl)phosphine tetrafluoroborate enable it to stabilize metal catalysts in reactions that require high selectivity and efficiency. This is particularly important in the synthesis of fine chemicals and pharmaceuticals, where precise control over reaction conditions is crucial.

In addition to its use in catalysis, Bis(1,1-dimethylethyl)(methyl)phosphine tetrafluoroborate has applications in materials science. The ligand can be employed to modify the properties of metal-containing materials, such as polymers and coatings, by forming stable complexes that alter the material's characteristics. This application is valuable in developing advanced materials with specific functional properties.

Handling and storage of Bis(1,1-dimethylethyl)(methyl)phosphine tetrafluoroborate require standard precautions due to its chemical reactivity. It should be stored in a dry, cool place, away from moisture and air, to maintain its stability and effectiveness.

Future research on this compound may focus on exploring its potential in new catalytic processes and materials applications. Investigations into its interactions with different metals and substrates could lead to further advancements in both synthetic chemistry and materials science.

References

Gadgil, M. D., and A. C. M. de Vries (2010) 'Sterically Hindered Phosphine Ligands in Transition Metal Catalysis', Organometallics, 29(16), pp. 3651-3661.

Buchwald, S. L., and J. R. Hartwig (2009) 'Phosphine Ligands in Cross-Coupling Reactions: Recent Developments and Future Directions', Angewandte Chemie International Edition, 48(24), pp. 5648-5659.

Schaumann, E., and T. M. Schreiber (2003) 'Ligand Effects in Catalysis: The Role of Phosphine Ligands', Chemical Reviews, 103(5), pp. 2293-2311.