Bis(3,5-dimethylphenyl)phosphine
[CAS# 71360-06-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: Bis(3,5-dimethylphenyl)phosphine
• Molecular Formula: C₁₆H₁₉P
• Molecular Weight: 242.30
• CAS Registry Number: 71360-06-0
• EC Number: 636-109-0
• SMILES: CC1=CC(=CC(=C1)PC2=CC(=CC(=C2)C)C)C

Properties

• Boiling Point: 368.8±42.0 °C (760 mmHg), Calc.^*
• Flash Point: 176.9±27.9 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Skin sensitization	Skin Sens.	1B	H317
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Pyrophoric liquids	Pyr. Liq.	1	H250

Discovery and Applications

Bis(3,5-dimethylphenyl)phosphine is a significant chemical compound known for its unique properties and applications in various fields of chemistry. This compound, featuring two 3,5-dimethylphenyl groups attached to a central phosphorus atom, is part of the phosphine family, which is recognized for its utility in coordination chemistry and catalysis.

The discovery of Bis(3,5-dimethylphenyl)phosphine can be attributed to ongoing research into phosphine ligands, which are critical in many chemical reactions due to their ability to stabilize transition metals and influence reaction pathways. The synthesis of this compound involves the reaction of 3,5-dimethylphenylchloride with a suitable phosphorus reagent, resulting in the formation of the bis-phosphine compound. This process typically requires careful handling and specific conditions to ensure the correct formation of the desired product.

One of the primary applications of Bis(3,5-dimethylphenyl)phosphine is in the field of homogeneous catalysis. The compound acts as a ligand that coordinates with transition metals to form metal-phosphine complexes. These complexes are valuable in a variety of catalytic processes, including hydrogenation, carbon-carbon coupling reactions, and other transformations. The steric and electronic properties of the 3,5-dimethylphenyl groups influence the reactivity and selectivity of the metal complexes, making Bis(3,5-dimethylphenyl)phosphine an important tool in organic synthesis.

In addition to its role in catalysis, Bis(3,5-dimethylphenyl)phosphine is used in the development of new materials. The compound’s ability to form stable metal complexes makes it useful in the design of materials with specific electronic or optical properties. For example, metal-phosphine complexes featuring Bis(3,5-dimethylphenyl)phosphine can be employed in the creation of organic light-emitting diodes (OLEDs) or other electronic devices where precise control over the metal-ligand interactions is crucial.

The compound’s application extends to medicinal chemistry as well. In some cases, Bis(3,5-dimethylphenyl)phosphine and its metal complexes have been investigated for their potential biological activities. For instance, they may be used as part of drug delivery systems or as agents in medicinal chemistry research to explore new therapeutic options.

The unique characteristics of Bis(3,5-dimethylphenyl)phosphine, including the bulkiness and electronic effects of the 3,5-dimethylphenyl groups, provide significant advantages in its applications. The steric hindrance introduced by these groups can affect the coordination environment of the central phosphorus atom, influencing the behavior of the resulting metal complexes. This makes the compound particularly valuable for reactions where control over steric and electronic factors is important.

In summary, Bis(3,5-dimethylphenyl)phosphine is a notable compound in the field of chemistry due to its role as a versatile ligand in catalysis and materials science. Its ability to form stable complexes with transition metals and its unique steric and electronic properties make it a valuable tool in various chemical applications. Ongoing research continues to explore its potential in new areas, highlighting its importance in both fundamental and applied chemistry.

References

2012. Organocatalytic Chemoselective Reduction of Phosphine Oxides to Phosphines. Synfacts, 2012(12).
DOI: 10.1055/s-0032-1317901

2006. Dramatic Ligand Effect in Catalytic Asymmetric Reductive Aldol Reaction of Allenic Esters to Ketones. Journal of the American Chemical Society, 128(43).
DOI: 10.1021/ja0652565