2,4,6-Tris[3-(diphenylphosphinyl)phenyl]-1,3,5-triazine
[CAS# 1646906-26-4]

Identification

• Classification: Pharmaceutical intermediate >> OLED material intermediate
• Name: 2,4,6-Tris[3-(diphenylphosphinyl)phenyl]-1,3,5-triazine
• Synonyms: PO-T2T
• Molecular Formula: C₅₇H₄₂N₃O₃P₃
• Molecular Weight: 909.88
• CAS Registry Number: 1646906-26-4
• EC Number: 891-419-5
• SMILES: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)C3=CC=CC(=C3)C4=NC(=NC(=N4)C5=CC(=CC=C5)P(=O)(C6=CC=CC=C6)C7=CC=CC=C7)C8=CC(=CC=C8)P(=O)(C9=CC=CC=C9)C1=CC=CC=C1

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.713, Calc.^*

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

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
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

2,4,6-Tris[3-(diphenylphosphinyl)phenyl]-1,3,5-triazine is a compound that has attracted attention due to its unique structure and potential applications in various fields, particularly in the area of catalysis and organic electronics. This molecule consists of a central 1,3,5-triazine ring with three 3-(diphenylphosphinyl)phenyl groups attached at the 2, 4, and 6 positions. The presence of the diphenylphosphinyl groups, which are known for their strong electron-withdrawing nature, plays a significant role in the compound's reactivity and its ability to interact with metal centers in catalytic processes.

The discovery of 2,4,6-Tris[3-(diphenylphosphinyl)phenyl]-1,3,5-triazine is part of ongoing research into triazine-based ligands, which have shown promise in coordination chemistry and catalysis. Triazine derivatives are highly regarded in the development of catalysts due to their ability to stabilize metal ions and promote reactions. The diphenylphosphinyl groups in the molecule enhance its coordination ability, making it a strong candidate for use in metal-catalyzed reactions, such as cross-coupling reactions and hydrogenation.

One of the key applications of 2,4,6-Tris[3-(diphenylphosphinyl)phenyl]-1,3,5-triazine is in catalysis, particularly in the development of efficient and selective catalysts for organic transformations. The phosphine groups act as ligands, coordinating with transition metals like palladium or platinum to facilitate various chemical reactions. These reactions are crucial for the synthesis of complex organic molecules, such as pharmaceuticals and agrochemicals. The ability of this compound to form stable complexes with metal ions makes it an essential building block for catalytic systems that require high stability and reactivity.

In addition to its catalytic applications, 2,4,6-Tris[3-(diphenylphosphinyl)phenyl]-1,3,5-triazine has shown potential for use in organic electronics. The electron-rich nature of the diphenylphosphinyl groups and the structural stability provided by the triazine core allow this compound to function as an efficient electron transporter in organic semiconductors. It could be applied in organic light-emitting diodes (OLEDs) or organic field-effect transistors (OFETs), where materials that can efficiently transport charge are critical for device performance.

The synthesis of 2,4,6-Tris[3-(diphenylphosphinyl)phenyl]-1,3,5-triazine typically involves the reaction of a suitable triazine derivative with diphenylphosphine oxide or its precursor, followed by selective functionalization to introduce the diphenylphosphinyl groups at the desired positions on the aromatic rings. The synthesis process requires careful control of reaction conditions to ensure the formation of the desired product and to optimize its performance in catalytic or electronic applications.

In conclusion, 2,4,6-Tris[3-(diphenylphosphinyl)phenyl]-1,3,5-triazine is a promising compound with significant applications in catalysis and organic electronics. Its unique structure, which combines a stable triazine core with electron-withdrawing phosphine groups, makes it an excellent candidate for metal-catalyzed reactions and organic semiconductor devices. Future research will likely focus on exploring its potential in other catalytic processes and optimizing its properties for use in electronic devices.

References

2024. Microsecond-response perovskite light-emitting diodes for active-matrix displays. Nature Electronics, 7(6), 458-467.
DOI: 10.1038/s41928-024-01181-5

2024. Enhancing crystal integrity and structural rigidity of CsPbBr3 nanoplatelets to achieve a narrow color-saturated blue emission. Light: Science & Applications, 13(1), 111.
DOI: 10.1038/s41377-024-01441-1

2021. High-performance quasi-2D perovskite light-emitting diodes: from materials to devices. Light: Science & Applications, 10(1), 61.
DOI: 10.1038/s41377-021-00501-0