Cas no 91575-92-7 ((E,E)-2,4-Heptadienyldiphenylphosphine Oxide)

(E,E)-2,4-Heptadienyldiphenylphosphine Oxide is a phosphine oxide derivative characterized by its conjugated diene structure, which enhances its reactivity in organometallic and coordination chemistry applications. The compound’s (E,E)-configuration ensures stereochemical stability, making it valuable as a ligand precursor or intermediate in catalytic processes. Its diphenylphosphine oxide moiety contributes to electron-withdrawing properties, facilitating selective transformations in cross-coupling and polymerization reactions. The extended conjugation also offers potential utility in materials science, particularly in designing photoactive or optoelectronic systems. This compound is typically handled under inert conditions due to its sensitivity to air and moisture, ensuring optimal performance in synthetic applications.
(E,E)-2,4-Heptadienyldiphenylphosphine Oxide structure
91575-92-7 structure
Product Name:(E,E)-2,4-Heptadienyldiphenylphosphine Oxide
CAS No:91575-92-7
MF:C19H21OP
MW:296.343206167221
CID:799927
PubChem ID:6284934
Update Time:2025-05-24

(E,E)-2,4-Heptadienyldiphenylphosphine Oxide Chemical and Physical Properties

Names and Identifiers

    • (E,E)-2,4-Heptadienyldiphenylphosphine Oxide
    • Phosphine oxide,2,4-heptadienyldiphenyl-, (E,E)- (9CI)
    • ((2E,4E)-Hepta-2,4-dien-1-yl)diphenylphosphine oxide
    • 91575-92-7
    • [[(2E,4E)-hepta-2,4-dienyl]-phenylphosphoryl]benzene
    • DB-246816
    • (2E,4e)-2,4-heptadien-1-yl(diphenyl)phosphine oxide
    • Inchi: 1S/C19H21OP/c1-2-3-4-5-12-17-21(20,18-13-8-6-9-14-18)19-15-10-7-11-16-19/h3-16H,2,17H2,1H3/b4-3+,12-5+
    • InChI Key: VZPNYAAYIKMMRT-ZDHPXMGNSA-N
    • SMILES: P(C1C=CC=CC=1)(C1C=CC=CC=1)(C/C=C/C=C/CC)=O

Computed Properties

  • Exact Mass: 296.13300
  • Monoisotopic Mass: 296.133002287g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 21
  • Rotatable Bond Count: 6
  • Complexity: 362
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 2
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 4.4
  • Topological Polar Surface Area: 17.1?2

Experimental Properties

  • Melting Point: 101-103°C
  • PSA: 26.88000
  • LogP: 4.52290

(E,E)-2,4-Heptadienyldiphenylphosphine Oxide Pricemore >>

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SHENG KE LU SI SHENG WU JI SHU
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Additional information on (E,E)-2,4-Heptadienyldiphenylphosphine Oxide

(E,E)-2,4-Heptadienyldiphenylphosphine Oxide: A Comprehensive Overview

(E,E)-2,4-Heptadienyldiphenylphosphine Oxide, with the CAS registry number 91575-92-7, is a compound of significant interest in the fields of organic chemistry and materials science. This compound, also referred to as diphenyl (E,E)-2,4-heptadienylphosphine oxide, is a derivative of diphenylphosphine oxide with a conjugated diene system attached to the phosphorus atom. The presence of the conjugated diene system introduces unique electronic and structural properties, making it a valuable molecule for various applications.

The molecular formula of this compound is C19H18PO, and its molecular weight is approximately 306.36 g/mol. The structure consists of two phenyl groups attached to a phosphorus atom, which is further connected to a hepta-2,4-dienyl group. The (E,E) configuration of the double bonds in the hepta-2,4-dienyl group ensures a planar arrangement, enhancing the conjugation and stability of the molecule. This configuration also plays a crucial role in determining the compound's electronic properties and reactivity.

(E,E)-2,4-Heptadienyldiphenylphosphine Oxide is typically synthesized via the oxidation of its corresponding phosphine precursor. The synthesis involves controlled oxidation conditions to ensure the formation of the desired oxide without overoxidation or side reactions. The compound is stable under normal conditions but may undergo thermal decomposition at elevated temperatures.

In terms of physical properties, this compound is typically a pale yellow crystalline solid with a melting point around 85°C and a boiling point above 300°C under standard pressure. It is sparingly soluble in water but exhibits good solubility in organic solvents such as dichloromethane, chloroform, and ethyl acetate. These solubility characteristics make it suitable for use in various organic synthesis reactions where precise control over reactivity is essential.

The electronic structure of (E,E)-2,4-Heptadienyldiphenylphosphine Oxide has been extensively studied using computational chemistry methods such as density functional theory (DFT). These studies have revealed that the molecule exhibits significant conjugation across the diene system and the phosphorus atom, leading to unique electronic transitions that are relevant for applications in optoelectronics and sensing technologies.

One of the most promising applications of this compound lies in its use as a precursor for advanced materials such as phosphorus-containing polymers and low-dimensional nanomaterials. Recent research has demonstrated that this compound can serve as a building block for constructing functional polymers with tailored electronic properties. For instance, incorporating this compound into polymer backbones has been shown to enhance charge transport properties, making them suitable for use in organic photovoltaic devices.

In addition to its role in polymer synthesis, (E,E)-2,4-Heptadienyldiphenylphosphine Oxide has also found applications in catalytic systems. Its ability to act as a Lewis base makes it an effective ligand in transition metal-catalyzed reactions. Recent studies have highlighted its potential as a ligand in palladium-catalyzed cross-coupling reactions, where it enhances catalytic activity and selectivity by stabilizing key intermediates during the reaction process.

The optical properties of this compound have also been explored for potential applications in fluorescence sensing and imaging. Due to its extended conjugation system, it exhibits strong absorption and emission characteristics in the visible region of the spectrum. Researchers have investigated its use as a fluorescent probe for detecting specific analytes in complex biological systems, demonstrating high sensitivity and selectivity.

From an environmental standpoint, understanding the fate and behavior of (E,E)-2,4-Heptadienyldiphenylphosphine Oxide in natural systems is crucial for assessing its potential impact on ecosystems. Recent studies have focused on its biodegradation pathways under aerobic and anaerobic conditions. These studies suggest that while the compound is relatively stable under ambient conditions, it can undergo microbial degradation under specific environmental conditions.

In conclusion, (E,E)-2,4-Heptadienyldiphenylphosphine Oxide (CAS No: 91575-92-7) is a versatile compound with diverse applications across multiple disciplines. Its unique electronic structure and reactivity make it an invaluable tool for researchers working on advanced materials development and catalytic processes. As ongoing research continues to uncover new insights into its properties and applications, this compound is poised to play an increasingly important role in both academic research and industrial applications.

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