Pentyltriphenylphosphonium bromide
[CAS# 21406-61-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: Pentyltriphenylphosphonium bromide
• Molecular Formula: C₂₃H₂₆P.Br
• Molecular Weight: 413.33
• CAS Registry Number: 21406-61-1
• EC Number: 244-374-5
• SMILES: CCCCC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]

Properties

• Melting point: 165 °C

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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Pentyltriphenylphosphonium bromide is an important chemical compound within the field of organophosphorus chemistry, noted for its applications in various synthetic and catalytic processes. This compound consists of a triphenylphosphonium cation with a pentyl group and a bromide anion. Its distinctive structure contributes to its effectiveness and versatility in several chemical applications.

The discovery of pentyltriphenylphosphonium bromide can be traced back to research focusing on the development of new phosphonium salts and their applications in organic synthesis. The synthesis of this compound typically involves the reaction of triphenylphosphine with pentyl bromide, resulting in the formation of the pentyltriphenylphosphonium cation paired with a bromide anion. This reaction yields a phosphonium salt with a long alkyl chain that imparts unique properties to the compound.

One of the key applications of pentyltriphenylphosphonium bromide is in phase-transfer catalysis. In this role, the compound functions as a phase-transfer catalyst, facilitating the transfer of reactants between immiscible phases, such as organic and aqueous phases. This property is particularly useful in reactions where one reactant is insoluble in the other phase. The phosphonium cation of pentyltriphenylphosphonium bromide can efficiently mediate the transfer of ions and molecules, thereby accelerating the reaction and improving yield.

Pentyltriphenylphosphonium bromide is also utilized in the synthesis of various organic compounds. It acts as a reagent in several chemical transformations, including nucleophilic substitutions and additions. Its ability to stabilize intermediates and enhance reaction rates makes it a valuable tool in organic synthesis, contributing to the development of new materials and pharmaceuticals.

In addition to its role in catalysis and synthesis, pentyltriphenylphosphonium bromide is employed in research to explore the behavior of phosphonium salts and their interactions with different substrates. The compound's unique properties and reactivity provide insights into the mechanisms of phase-transfer catalysis and the design of new catalytic systems.

Overall, pentyltriphenylphosphonium bromide is a versatile and valuable compound in organophosphorus chemistry. Its applications in phase-transfer catalysis and organic synthesis highlight its significance in advancing chemical processes and developing new materials.

References

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