726-61-4

Basic information

• Product Name: diethyl 4-vinylbenzylphosphonate
• Synonyms: Phosphonic acid, [(4-ethenylphenyl)methyl]-, diethyl ester;4-Vinylbenzylphosphonic acid diethyl ester;diethyl 4-vinylbenzylphosphonate
• CAS NO: 726-61-4
• Molecular Formula: C₁₃H₁₉O₃P
• Molecular Weight: 254.261921
• EINECS: -0
• Product Categories: Chloromethy styrene
• Mol File: 726-61-4.mol

Chemical Properties

• Boiling Point: 120 °C(Press: 0.2 Torr)
• Appearance: /
• Density: 1.083±0.06 g/cm3(Predicted)
• CAS DataBase Reference: diethyl 4-vinylbenzylphosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl 4-vinylbenzylphosphonate(726-61-4)
• EPA Substance Registry System: diethyl 4-vinylbenzylphosphonate(726-61-4)

Safety Data

• Hazardous Substances Data: 726-61-4(Hazardous Substances Data)

Usage

Uses

Used in Flame-Retardant Materials:
Diethyl 4-vinylbenzylphosphonate is used as a monomer for the production of flame-retardant materials, providing enhanced fire safety properties to various products.
Used in Specialty Coatings and Adhesives:
Diethyl 4-vinylbenzylphosphonate is used as a chemical intermediate in the development of specialty coatings and adhesives, contributing to their unique properties and performance.
Used in Chemical Synthesis:
Diethyl 4-vinylbenzylphosphonate is utilized as a chemical intermediate in the synthesis of other organic compounds, enabling the creation of a wide range of products across different industries.

Upstream product

• 1592-20-7 4-Vinylbenzyl chloride 
• 2303-76-6 sodium diethyl phosphite 
• 74-85-1 ethene 
• 38186-51-5 diethyl (4-bromobenzyl)phosphonate 
• 762-04-9 phosphonic acid diethyl ester 
• 45817-37-6 4-vinylbenzyl iodide 
• 122-52-1 triethyl phosphite 

Downstream Products

• 670274-19-8 4-(4'-(methylthio)styryl)styrene 
• 134060-87-0 diphenyl-{4-[2-(4-vinyl-phenyl)-vinyl]-phenyl}-amine 

Relevant articles and documents

Synthesis and solid-state NMR studies of P-vinylbenzylphosphonic acid

P-Vinylbenzylphosphonic acid (2) was synthesized and crystallized in two phases A and B. The latter phase was easily converted into the former. Both phases were investigated by IR and solid-state 31P and 1H NMR spectroscopy, and X-ra

Oxidative Dephosphorylation of Benzylic Phosphonates with Dioxygen Generating Symmetrical trans-Stilbenes

Under a dioxygen atmosphere, benzylphosphonates and related phosphoryl compounds can readily produce the corresponding trans-stilbenes in high yields with high selectivity upon treatment with bases. Various functional groups were tolerable under the reaction conditions.

Preparation and Photophysical Properties of All-trans Acceptor-π-Donor (Acceptor) Compounds Possessing Obvious Solvatochromic Effects

A series of all-trans acceptor-π-donor (acceptor) compounds (BAQ, SFQ, BLQ, and XJQ) were conveniently synthesised and characterised by infrared, nuclear magnetic resonance, mass spectrometry, and elemental analysis. Their photophysical properties, including linear absorption, one-photon excited fluorescence, two-photon absorption, and two-photon excited fluorescence, were systematically investigated. All the compounds show obvious solvatochromic effects, such as significant bathochromic shifts of the emission spectra and larger Stokes shifts in more polar solvents. Under excitation from a femtosecond Ti:sapphire laser with a pulse width of 140 fs, they all exhibit strong two-photon excited fluorescence, and the two-photon absorption cross-sections in THF are 851 (BAQ), 216 (SFQ), 561 (BLQ), and 447 (XJQ) GM respectively. A combination of density functional theory (DFT) and time-dependent density functional theory (TDDFT) approaches was used to investigate the relationships between the structures and the photophysical properties of these compounds. The results show that they may have a potential application as polarity-sensitive two-photon fluorescent probes.

Polyfluorenylacetylene for near-infrared laser protection: Polymer synthesis, optical limiting mechanism and relationship between molecular structure and properties

A series of functional polyacetylenes bearing the fluorene moiety with different conjugated lengths and terminal substituents, poly[2-ethynyl-7-(4-nitrostyryl)-9,9-dioctyl-9H-fluorene] (P1), poly[2-ethynyl-7-(4-(4-nitrostyryl)styryl)-9,9-dioctyl-9H-fluorene] (P2), poly[2-ethynyl-7-(4-(4-methoxystyryl)styryl)-9,9-dioctyl-9H-fluorene] (P3), poly[2-ethynyl-7-(4-(4-methylstyryl)styryl)-9,9-dioctyl-9H-fluorene] (P4), and poly[2-ethynyl-7-(4-(4-methylstyryl)styryl)-9,9-didodecyl-9H-fluorene] (P5), were designed and prepared using [Rh(nbd)Cl]2 as the catalyst. Their structures and properties were characterized and evaluated by FTIR, NMR, UV, FL, GPC and TGA analyses. The optical limiting properties were investigated using 450 fs laser pulses at 780 nm. These results show that the incorporation of styryl/stilbene functionalized polyfluorenylacetylenes has endowed resultant polyacetylenes with novel near-infrared laser protection properties and enhanced thermal stability. The optical limiting mechanism for laser protection was studied. It was found that the optical limiting properties mainly originated from two-photon absorption (TPA) of molecules in the resulting polyacetylenes. Additionally, it was also found that the functionalized polyacetylene with a longer fluorene-based conjugated chromophore and a stronger terminal electron acceptor group exhibits better optical limiting properties because of the larger π-electron delocalization and dipolar effect.

A new series of two-photon blue/violet fluorescent trans-alkenes: Green synthesis and optical properties

A new series of trans-alkenes (3a-3e) containing different electron-donating groups were synthesized by the solvent-free Horner-Wadsworth-Emmons reaction, and characterized by infrared, hydrogen nuclear magnetic resonance, mass spectrometry and elemental analysis. Their UV-visible absorption, one-photon excited fluorescence, two-photon absorption, and two-photon excited fluorescence were systematically investigated in different solvents. Experimental results show different trends in linear and nonlinear optical properties with different donor units. 3a with triphenylamine donor exhibits the best optical properties. It emits strong blue up-converted fluorescence, and the two-photon absorption cross-section can be as large as 218 GM in DCM.

Synthesis, optical characterization, and solvatochromism study of new two-photon absorption compounds

The new donor-π-acceptor/acceptor-π-acceptor compounds (FQQ, KZQ, JYQ, and LVQ) were facilely synthesized and characterized by infrared, proton nuclear magnetic resonance, mass spectrometry, and elemental analysis. Their UV-visible absorption, one-photon excited fluorescence, two-photon absorption, and two-photon excited fluorescence were systematically investigated in different solvents. The experiment results indicate that all these compounds exhibit relatively strong up-converted fluorescence and obvious solvatochromic effects. KZQ shows the largest σ value of 707 GM in THF upon 830 nm excitation. Its excellent optical properties provide a promising alternative as a polarity-sensitive two-photon fluorescent probe. Aided with the quantum chemical density functional theory calculations, the relationships between the structures and the properties were studied.

Phosphonate-functionalized polystyrene microspheres with controlled zeta potential for efficient uranium sorption

It is significant to develop new methods to capture uranium from aqueous solution for environment and human health benefits. We report here phosphonate-functionalized polystyrene microspheres with controlled zeta potentials for efficient sorption of uranium(vi) from aqueous solution. The microspheres are prepared by emulsion polymerization with diethyl-(4-vinylbenzyl) phosphonate as a comonomer and emulsifier, and the zeta potentials can be controlled with different kinds of initiators. The sorbents with high positive zeta potentials show faster rate and higher selectivity than the negative ones. The process follows a second-order kinetics model, and can reach equilibrium with a capacity of 83.4 mg U g-1 in a single-element solution of uranium (200 ppm) within 200 min at pH 8.0 and 298.15 K. There are relatively larger capacities for sorbents with a high zeta potential than the neutral ones. Furthermore, the sorbents can be efficiently regenerated and reused well after five cycles. This work may provide a new approach for highly efficient sorption of uranium(vi) from aqueous solution.

Preparation of benzylphosphonates via a palladium(0)-catalyzed cross-coupling of H-phosphonate diesters with benzyl halides. Synthetic and mechanistic studies

We have developed a new, efficient method for the synthesis of benzylphosphonate and benzylphosphonothioate diesters via a palladium(0)- catalyzed cross-coupling reaction between benzyl halides and H-phosphonate or H-phosphonothioate diesters, using Pd2(dba)3(CHCl 3) as a palladium source and Xantphos as a supporting ligand. Some mechanistic aspects of these reactions were investigated using 31P NMR spectroscopy.

HOLE TRANSPORT POLYMER FOR USE IN ELECTRONIC DEVICES

Organic light emitting diode (OLED) devices are one of the most promising alternatives to liquid crystal displays (LCDs) for flat panel display (FPD) applications. The OLED technique is based on organic semiconductors used either as hole- or electron tran

Synthesis of ferrocenethiols containing oligo(phenylenevinylene) bridges and their characterization on gold electrodes

Ferrocene-terminated oligo(phenylenevinylene) (OPV) methyl thiols have been prepared by orthogonal coupling of phenylene monomers. Ethoxy substituents on the phenyl rings improve the solubility of OPV, enabling the synthesis of longer oligomers. Self-assembled monolayers containing a mixture of a ferrocene OPV methyl thiol and a diluent alkanethiol were deposited on gold. A cyclic voltammetric study of monolayers containing oligomers of the same length with and without ethoxy solubilizing groups reveals that both solubilized and unsolubilized oligomers form well-packed self-assembled monolayers. Changing the position of the solubilizing groups on an oligomer chain does not preclude packing of the oligomer in the monolayer. Conventional chronoamperometry, which can be used to measure rate constants up to ～104 S-1, is too slow to measure the electron-transfer rate through these oligomers over distances up to 35 A. OPV bridges are expected to be highly conjugated unlike oligo(phenyleneethynylene) bridges, which may be only partially conjugated because of rotation of the phenyl rings about the ethynylene bonds. Because of its high conjugation, OPV may prove useful as a molecular wire.