Cas no 25361-69-7 (Phosphonium,(2-ethoxyethyl)triphenyl-, bromide (1:1))

Phosphonium, (2-ethoxyethyl)triphenyl-, bromide (1:1) is a quaternary phosphonium salt with applications in organic synthesis and phase-transfer catalysis. Its structure, featuring a 2-ethoxyethyl group and three phenyl rings attached to a central phosphorus atom, enhances solubility in polar organic solvents while maintaining stability under various reaction conditions. The bromide counterion further improves reactivity in nucleophilic substitution and alkylation reactions. This compound is particularly useful in Wittig reactions, where it serves as a precursor for stabilized ylides. Its balanced lipophilicity and ionic character make it effective in facilitating reactions between immiscible phases, offering consistent performance in synthetic workflows.
Phosphonium,(2-ethoxyethyl)triphenyl-, bromide (1:1) structure
25361-69-7 structure
Product Name:Phosphonium,(2-ethoxyethyl)triphenyl-, bromide (1:1)
CAS No:25361-69-7
MF:C22H24BrOP
MW:415.303126335144
MDL:MFCD27937860
CID:275237
PubChem ID:24189128
Update Time:2025-06-26

Phosphonium,(2-ethoxyethyl)triphenyl-, bromide (1:1) Chemical and Physical Properties

Names and Identifiers

    • Phosphonium,(2-ethoxyethyl)triphenyl-, bromide (1:1)
    • 2-ethoxyethyl(triphenyl)phosphanium,bromide
    • (2-ethoxyethyl)triphenylphosphonium bromide
    • 2-Ethoxyethyltriphenylphosphonium-Ion
    • NSC84061
    • 25361-69-7
    • AB86661
    • NSC-84061
    • (2-Ethoxyethyl)(triphenyl)phosphanium bromide
    • 2-ethoxyethyl(triphenyl)phosphanium;bromide
    • SXPXVPGJBRZVLW-UHFFFAOYSA-M
    • CS-0433445
    • DTXSID70637549
    • C78099
    • (2-Ethoxyethyl)triphenylphosphoniuMbroMide
    • SCHEMBL17511368
    • MDL: MFCD27937860
    • Inchi: 1S/C22H24OP.BrH/c1-2-23-18-19-24(20-12-6-3-7-13-20,21-14-8-4-9-15-21)22-16-10-5-11-17-22;/h3-17H,2,18-19H2,1H3;1H/q+1;/p-1
    • InChI Key: SXPXVPGJBRZVLW-UHFFFAOYSA-M
    • SMILES: [Br-].[P+](C1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)CCOCC

Computed Properties

  • Exact Mass: 335.15662
  • Monoisotopic Mass: 414.07481g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 25
  • Rotatable Bond Count: 7
  • Complexity: 292
  • Covalently-Bonded Unit Count: 2
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 9.2?2

Experimental Properties

  • PSA: 9.23
  • LogP: 1.02100

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Additional information on Phosphonium,(2-ethoxyethyl)triphenyl-, bromide (1:1)

Phosphonium,(2-ethoxyethyl)triphenyl-, bromide (1:1) - A Comprehensive Overview

The compound with CAS No 25361-69-7, commonly referred to as Phosphonium,(2-ethoxyethyl)triphenyl-, bromide (1:1), is a significant entity in the field of organic chemistry. This compound is a phosphonium salt, characterized by its unique structure and versatile applications. The phosphonium core of the molecule is a central phosphorus atom bonded to three phenyl groups and an ethoxyethyl group, making it a highly stable and reactive species. The bromide counterion plays a crucial role in maintaining the ionic balance of the compound.

Recent studies have highlighted the importance of phosphonium salts in various chemical reactions, particularly in organocatalysis and asymmetric synthesis. The (2-ethoxyethyl)triphenylphosphonium bromide has been found to act as an effective catalyst in enantioselective reactions, offering high yields and excellent stereocontrol. This has made it a valuable tool in the synthesis of complex organic molecules, including pharmaceutical intermediates and natural product analogs.

The synthesis of Phosphonium,(2-ethoxyethyl)triphenyl-, bromide (1:1) involves a multi-step process, typically starting with the reaction of triphenylphosphine with an alkyl halide. The ethoxyethyl group is introduced via an alkylation step, followed by protonation to form the phosphonium salt. The bromide ion is then incorporated as the counterion. This compound is highly soluble in polar solvents, making it suitable for use in various solution-phase reactions.

In terms of applications, Phosphonium,(2-ethoxyethyl)triphenyl-, bromide (1:1) has found extensive use in the pharmaceutical industry. Its ability to facilitate enantioselective reactions has led to its adoption in the synthesis of chiral drugs and biologically active compounds. Additionally, this compound has been employed in the development of novel materials, such as polymers and nanoparticles, due to its unique electronic properties.

Recent advancements in computational chemistry have provided deeper insights into the electronic structure and reactivity of phosphonium salts like Phosphonium,(2-ethoxyethyl)triphenyl-, bromide (1:1). Quantum mechanical calculations have revealed that the ethoxyethyl group significantly influences the electronic distribution around the phosphorus atom, enhancing its nucleophilicity and reactivity. These findings have paved the way for new strategies in catalytic asymmetric synthesis.

The stability and reactivity of Phosphonium,(2-ethoxyethyl)triphenyl-, bromide (1:1) make it an ideal candidate for use in industrial-scale chemical processes. Its ability to function as both a catalyst and a reagent in various transformations underscores its versatility. Furthermore, ongoing research into its application in sustainable chemistry has opened up new avenues for green chemical synthesis.

In conclusion, Phosphonium,(2-ethoxyethyl)triphenyl-, bromide (1:1) is a versatile and valuable compound with wide-ranging applications in organic chemistry. Its unique structure and reactivity continue to make it a focal point for researchers seeking innovative solutions in drug discovery, material science, and sustainable chemical processes.

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