2-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromide
[CAS# 69891-92-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: 2-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromide
• Molecular Formula: C₂₄H₂₆O₂P^.Br
• Molecular Weight: 457.34
• CAS Registry Number: 69891-92-5
• EC Number: 274-189-5
• SMILES: C1COC(OC1)CC[P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.[Br-]

Properties

• Melting point: 193-195 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
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

2-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromide is a notable compound in organophosphorus chemistry, characterized by its unique structure and various applications. The compound, with the chemical formula C22H23BrO2P, consists of a triphenylphosphonium cation and a 1,3-dioxane moiety attached through an ethyl bridge, combined with a bromide anion.

The discovery of 2-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromide can be traced back to the ongoing development of organophosphorus compounds in the mid-20th century. The synthesis of this compound involves the reaction of triphenylphosphine with 2-(1,3-dioxan-2-yl)ethyl bromide. This reaction produces the desired phosphonium salt along with bromide as a byproduct. This synthetic route highlights the compound's formation and its ability to stabilize various intermediates through its triphenylphosphonium cation.

One of the primary applications of 2-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromide is in the field of organic synthesis as a phase-transfer catalyst. The compound's ability to facilitate the transfer of reactants between different phases—such as between aqueous and organic phases—makes it valuable in various chemical reactions. For instance, it is used to enhance the efficiency of nucleophilic substitution reactions, where it helps in the effective transfer of nucleophiles to organic substrates, thereby increasing reaction rates and yields.

In addition to its role as a phase-transfer catalyst, 2-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromide is employed in the synthesis of complex organic molecules. Its ability to stabilize reactive intermediates through the phosphonium cation makes it useful in the construction of diverse organic frameworks. This application is particularly important in the development of pharmaceuticals and other fine chemicals, where precise control over reaction conditions is crucial.

The compound also finds use in the field of materials science. Its unique structure allows it to act as a precursor for the synthesis of various phosphonium-containing polymers and materials. These materials are used in a range of applications, including the development of ion-exchange resins and other advanced functional materials. The ability of 2-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromide to form stable ionic interactions makes it valuable in creating materials with specific properties, such as high ionic conductivity or selective ion exchange capabilities.

Moreover, 2-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromide is studied for its potential applications in catalysis and chemical transformation processes. Its stability and reactivity make it an attractive candidate for various catalytic processes, including those involving organophosphorus compounds. Research into its use in catalysis continues to expand, highlighting its versatility and potential for novel applications.

Safety and environmental considerations are important when handling 2-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromide. Proper precautions should be taken to avoid exposure and ensure safe handling procedures, given its chemical reactivity and potential impact.

Overall, 2-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromide is a valuable compound in both organic synthesis and materials science. Its role as a phase-transfer catalyst, its applications in the synthesis of complex molecules, and its use in materials science underscore its importance in various chemical processes.