1,3-Bis[(di-tert-butylphosphino)methyl]benzene
[CAS# 149968-36-5]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: 1,3-Bis[(di-tert-butylphosphino)methyl]benzene
• Synonyms: ditert-butyl-[[3-(ditert-butylphosphanylmethyl)phenyl]methyl]phosphane
• Molecular Formula: C₂₄H₄₄P₂
• Molecular Weight: 394.55
• CAS Registry Number: 149968-36-5
• EC Number: 813-340-7
• SMILES: CC(C)(C)P(CC1=CC(=CC=C1)CP(C(C)(C)C)C(C)(C)C)C(C)(C)C

Properties

• Solubility: Insoluble (1.4E^-5 g/L) (25 °C), Calc.^*
• Melting point: 68-75 °C

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety 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

Discovery and Applications

1,3-Bis[(di-tert-butylphosphino)methyl]benzene is a notable chemical compound recognized for its distinctive structure and significant applications in the field of organophosphorus chemistry. This molecule, featuring a benzene ring with two di-tert-butylphosphino groups attached to the 1 and 3 positions, is valued for its role as a highly effective ligand in various chemical processes.

The discovery of 1,3-Bis[(di-tert-butylphosphino)methyl]benzene can be traced back to efforts to create robust and versatile ligands that could stabilize metal complexes and enhance catalytic reactions. The di-tert-butylphosphino groups provide a sterically hindered environment around the phosphorus atoms, which is crucial for stabilizing metal centers and influencing the reactivity of the complex. This steric hindrance helps to prevent the decomposition of metal-ligand complexes and improves the efficiency of catalysis.

The synthesis of 1,3-Bis[(di-tert-butylphosphino)methyl]benzene typically involves the reaction of di-tert-butylphosphine with a suitable benzyl derivative. The resulting ligand is then purified and characterized using various analytical techniques to confirm its structure and purity. The compound is known for its high thermal stability and resistance to oxidation, making it a reliable choice for demanding chemical environments.

One of the primary applications of 1,3-Bis[(di-tert-butylphosphino)methyl]benzene is in the field of homogeneous catalysis. The compound serves as a ligand in metal-catalyzed reactions, where it helps to stabilize transition metal centers and enhance the reactivity of the catalyst. For instance, it is commonly used in cross-coupling reactions, such as the Suzuki and Heck reactions, which are important methods for forming carbon-carbon bonds. The ligand's steric and electronic properties enable the formation of high-quality products with minimal side reactions.

Additionally, 1,3-Bis[(di-tert-butylphosphino)methyl]benzene is utilized in the development of new catalytic processes and materials. Its ability to form stable metal complexes makes it a valuable tool for designing new catalysts with tailored properties. The compound's high steric bulk also allows for the fine-tuning of catalytic activity and selectivity, which is essential for optimizing reactions and developing novel materials with specific functions.

In summary, 1,3-Bis[(di-tert-butylphosphino)methyl]benzene represents a significant advancement in organophosphorus chemistry. Its discovery has provided a valuable ligand for metal-catalyzed reactions, offering enhanced stability and reactivity for a range of catalytic processes. The compound's unique structural features and applications underscore its importance in both academic research and industrial applications.

References

2008. {2,6-Bis[(di-tert-butylphosphino)methyl]phenyl}chloridonickel(II). Acta crystallographica. Section E, Structure reports online, 64(10).
DOI: 10.1107/s1600536808029814

2004. CCDC 215279: Experimental Crystal Structure Determination. , .
DOI: 10.5517/cc770hy

2003. X-Ray Structural Analysis of NiII, PdII, and PtII Complexes with the Potentially Tridentate Ligand 1,3-Bis(diphenylphosphinomethyl)benzene, 1,3-C6H4(CH2PPh2)2. Structural Chemistry, 14(3).
DOI: 10.1023/a:1023859712448