Tris(4-methoxyphenyl)phosphine
[CAS# 855-38-9]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Tris(4-methoxyphenyl)phosphine
• Synonyms: trianisylphosphine
• Molecular Formula: C₂₁H₂₁O₃P
• Molecular Weight: 352.36
• CAS Registry Number: 855-38-9
• EC Number: 212-723-0
• SMILES: COC1=CC=C(C=C1)P(C2=CC=C(C=C2)OC)C3=CC=C(C=C3)OC

Properties

• Melting point: 133 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-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
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

Tris(4-methoxyphenyl)phosphine is a notable chemical substance that has garnered attention for its unique properties and diverse applications in organic synthesis and catalysis. This compound belongs to a class of organophosphorus compounds characterized by the presence of a phosphine center bonded to three 4-methoxyphenyl groups. Its synthesis and application highlight its significance in advancing various chemical processes.

The discovery of Tris(4-methoxyphenyl)phosphine is rooted in the broader study of phosphine ligands and their role in coordination chemistry. The synthesis of this compound typically involves the reaction of 4-methoxyphenyl lithium with a phosphorus trichloride precursor. This reaction forms the tris(4-methoxyphenyl)phosphine compound through a substitution process where the phosphine group replaces chlorine atoms on the phosphorus center.

The distinctive feature of Tris(4-methoxyphenyl)phosphine is its electronic and steric properties, which are imparted by the three 4-methoxyphenyl groups attached to the phosphine center. The methoxy groups enhance the electron-donating ability of the phosphine, which in turn influences its coordination behavior and reactivity. This makes it an effective ligand for various metal complexes, particularly in catalysis.

One of the primary applications of Tris(4-methoxyphenyl)phosphine is in the field of homogeneous catalysis. The compound is often used as a ligand in the formation of metal complexes, where it plays a crucial role in stabilizing metal centers and facilitating catalytic reactions. For example, metal complexes with Tris(4-methoxyphenyl)phosphine have been employed in a range of reactions, including cross-coupling reactions and olefin metathesis.

In cross-coupling reactions, Tris(4-methoxyphenyl)phosphine complexes serve as efficient catalysts for the formation of carbon-carbon bonds. The electronic properties of the phosphine ligand enhance the reactivity of the metal center, enabling the efficient coupling of various organic substrates. This application is particularly valuable in the synthesis of complex organic molecules and pharmaceuticals.

Another significant application of Tris(4-methoxyphenyl)phosphine is in olefin metathesis, a process used to rearrange carbon-carbon double bonds in olefins. The phosphine ligand stabilizes the metal center in metathesis catalysts, improving their efficiency and selectivity. This reaction is important in the synthesis of fine chemicals and polymers.

In addition to its catalytic applications, Tris(4-methoxyphenyl)phosphine is also used in the development of new materials. The compound's ability to form stable metal complexes makes it useful in creating materials with specific properties. These materials can be used in various industries, including electronics and materials science.

The versatility of Tris(4-methoxyphenyl)phosphine as a ligand and catalyst underscores its importance in both academic research and industrial applications. Its unique combination of electronic and steric effects makes it a valuable tool for chemists seeking to develop new reactions and materials.

References

2023. Poly(ether)s derived from oxa-Michael polymerization: a comprehensive review. Monatshefte für Chemie - Chemical Monthly, 154(3-4).
DOI: 10.1007/s00706-023-03049-4

2023. Novel Five-Coordinated Bis-Dioxolene Cobalt Complexes with Methoxy-Substituted Triarylphosphine. Russian Journal of General Chemistry, 93(12).
DOI: 10.1134/s1070363223160107

2019. Recent Advances in First-Row Transition Metal/Chiral Phosphoric Acid Combined Catalysis. Topics in Current Chemistry, 377(5).
DOI: 10.1007/s41061-019-0249-0