116130
Diethyl vinylphosphonate
97%
Synonym(s):
Vinylphosphonic acid diethyl ester
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About This Item
Linear Formula:
CH2=CHPO(OCH2CH3)2
CAS Number:
Molecular Weight:
164.14
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
211-663-2
Beilstein/REAXYS Number:
507596
MDL number:
Assay:
97%
InChI key
DREPONDJUKIQLX-UHFFFAOYSA-N
InChI
1S/C6H13O3P/c1-4-8-10(7,6-3)9-5-2/h6H,3-5H2,1-2H3
SMILES string
CCOP(=O)(OCC)C=C
assay
97%
Quality Level
bp
202 °C (lit.)
density
1.068 g/mL at 25 °C (lit.)
functional group
phosphonate
storage temp.
2-8°C
Related Categories
Application
Diethyl vinylphosphonate (DEVP) can be used as a precursor for the synthesis of:
It can be also employed as a monomer unit for the preparation of high-molecular-weight polymer, poly(diethyl vinylphosphonate) using lanthanide complexes.{18)
- α, β-unsaturated phosphonates by reacting with arylboronic acids via Pd-catalyzed Mizoroki−Heck reaction.
- 2-(arylamino)ethyl phosphonates by condensing with primary and secondary amines via the aza-Michael addition reaction.
It can be also employed as a monomer unit for the preparation of high-molecular-weight polymer, poly(diethyl vinylphosphonate) using lanthanide complexes.{18)
Diethyl vinylphosphonate has been used in the preparation of diethyl N-alkyl-2-aminoethylphosphonate.
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
230.0 °F - closed cup
flash_point_c
110 °C - closed cup
ppe
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
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Synthesis of 2-(arylamino) ethyl phosphonic acids via the aza-Michael addition on diethyl vinylphosphonate
Orm Nadine B, et al.
Tetrahedron, 69(1), 115-121 (2013)
Convenient synthesis of α, β-unsaturated phosphonates via a Mizoroki-Heck reaction of arylboronic acids with diethyl vinylphosphonate
Kabalka GW, et al.
Tetrahedron Letters, 45(24), 4685-4687 (2004)
Poly (vinylphosphonate) s synthesized by trivalent cyclopentadienyl lanthanide-induced group transfer polymerization
Salzinger S, et al.
Macromolecules, 44(15), 5920-5927 (2011)
Joachim E Klee et al.
Beilstein journal of organic chemistry, 5, 72-72 (2009-01-01)
Novel N-alkyl-N-(phosphonoethyl) substituted mono-, bis- and tris(meth)acrylamides 3 were synthesized by two different three-step reactions and characterized by IR, (1)H NMR and (13)C NMR spectroscopy as well as refractive index and viscosity. The phosphonoethyl substituted (meth)acrylamide monomers show improved hydrolytic
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