Diethyl vinylphosphonate

Base Information

• Chemical Name: Diethyl vinylphosphonate
• CAS No.: 682-30-4
• Molecular Formula: C6H13O3P
• Molecular Weight: 164.141
• Hs Code.: 29319090
• European Community (EC) Number: 211-663-2
• UNII: 8Y4RR2U2KA
• DSSTox Substance ID: DTXSID70218372
• Nikkaji Number: J205.987H
• Wikidata: Q83095244
• Mol file: 682-30-4.mol

Synonyms:Diethyl vinylphosphonate;682-30-4;Vinylphosphonic acid diethyl ester;Diethyl vinylphosphate;Diethoxyphosphinylethene;Phosphonic acid, vinyl-, diethyl ester;Diethylvinylphosphonate;diethyl ethenylphosphonate;Phosphonic acid, ethenyl-, diethyl ester;1-[ethenyl(ethoxy)phosphoryl]oxyethane;C6H13O3P;EINECS 211-663-2;MFCD00009079;BRN 0507596;8Y4RR2U2KA;Diethyl(vinyl)phosphonate;UNII-8Y4RR2U2KA;SCHEMBL282682;Diethyl vinylphosphonate, 97%;DTXSID70218372;vinyl-phosphonic acid diethyl ester;CS-D0588;Ethenephosphonic acid, diethyl ester;AKOS015915767;SY009918;LS-106815;D3728;FT-0632793;EN300-107820;F0001-1789

Chemical Property of Diethyl vinylphosphonate

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid
• Vapor Pressure: 0.474mmHg at 25°C
• Refractive Index: n20/D 1.429(lit.)
• Boiling Point: 199.8 °C at 760 mmHg
• Flash Point: 88.9 °C
• PSA: 45.34000
• Density: 1.028 g/cm³
• LogP: 2.39600
• Storage Temp.: 2-8°C
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 164.06023127
• Heavy Atom Count: 10
• Complexity: 134

Purity/Quality:

98%,99%, ^*data from raw suppliers

Diethyl Vinylphosphonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(C=C)OCC
• General Description: Diethyl vinylphosphonate is a reactive organophosphorus compound used in the synthesis of biologically active derivatives through nucleophilic addition reactions, such as with imidazole, where it forms β-imidazolyl-substituted phosphonates. These products exhibit potential biological activity and utility as complexing agents or extractants.

Technology Process of Diethyl vinylphosphonate

There total 36 articles about Diethyl vinylphosphonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

diethyl (α-methylselenenylethyl)phosphonate (80436-45-9) → Diethyl vinylphosphonate (682-30-4)

Guidance literature:

With pyridine; dihydrogen peroxide; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2004.10.026

Reference yield: 95.0%

Diethyl phosphonate (762-04-9,123-22-8) → Diethyl vinylphosphonate (682-30-4)

Guidance literature:

tetrakis(triphenylphosphine)palladium ⁽⁰⁾;

Reference yield: 91.0%

diethyl 2-bromoethylphosphonate (5324-30-1) → Diethyl vinylphosphonate (682-30-4)

Guidance literature:

With triethylamine; In benzene; for 1h; Reflux;

DOI:10.1002/pola.27990

upstream raw materials:

ethanol

vinyldichlorophosphine oxide

diethyl 2-chloroethylphosphonate

diethyl 2-bromoethylphosphonate

Downstream raw materials:

ethyl 2-phenylthioethylphosphonate

dimethyldiethylethane-1,2-diylphosphonate

diethyl (2-ethoxyethyl)phosphonate

diethyl 2-(N,N-dimethylamino)ethylphosphonate

Refernces

Reactions of allenyl- and vinylphosphonates with imidazole

10.1134/S107042800711019X

The research investigates the reactions of dialkyl allenyl- and vinylphosphonates with imidazole to synthesize new potential biologically active derivatives. The study aims to explore the synthesis and properties of alkenyl- and alkylphosphonates with nitrogen-containing heterocyclic substituents in the β-position, which have been underexplored. The key chemicals used include diethyl 3-methylbuta-1,2-dien-1-ylphosphonate, diisopropyl 3-methylbuta-1,2-dien-1-ylphosphonate, diethyl vinylphosphonate, and dibutyl vinylphosphonate. The findings indicate that imidazole adds to the β-carbon atom of the unsaturated fragment, yielding β-imidazolylalkenyl- and -alkylphosphonates. The study concludes that nucleophilic addition of imidazole to these phosphonates occurs at the β-carbon atom, and the resulting compounds have potential biological activity and could be used as complexing agents and extractants.

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