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

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Identification
ClassificationOrganic raw materials >> Organic phosphine compound
NameBis(1,1-dimethylethyl)(methyl)phosphine tetrafluoroborate
SynonymsDi-tert-butyl(methyl)phosphonium tetrafluoroborate
Molecular StructureCAS # 479094-62-7, Bis(1,1-dimethylethyl)(methyl)phosphine tetrafluoroborate
Molecular FormulaC9H21P.BF4.H
Molecular Weight248.05
CAS Registry Number479094-62-7
EC Number808-098-4
SMILES[B-](F)(F)(F)F.CC(C)(C)[PH+](C)C(C)(C)C
Properties
Melting point>230 °C
Safety Data
Hazard Symbolssymbol symbol   GHS05;GHS07 Danger  Details
Risk StatementsH314-H315-H319-H335  Details
Safety StatementsP260-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  Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Skin irritationSkin Irrit.2H315
Eye irritationEye Irrit.2H319
Specific target organ toxicity - single exposureSTOT SE3H335
Skin corrosionSkin Corr.1CH314
Serious eye damageEye Dam.1H318
Acute toxicityAcute Tox.4H302
SDSAvailable
up Discovery and Applications
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

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