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Sigma-Aldrich

Diethyl vinylphosphonate

97%

Synonym(s):

Vinylphosphonic acid diethyl ester

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About This Item

Linear Formula:
CH2=CHPO(OCH2CH3)2
CAS Number:
682-30-4
Molecular Weight:
164.14
Beilstein/REAXYS Number:
507596
EC Number:
211-663-2
MDL number:
MFCD00009079
UNSPSC Code:
12352100
PubChem Substance ID:
24847265
NACRES:
NA.22

Quality Level

100

assay

97%

refractive index

n20/D 1.429 (lit.)

bp

202 °C (lit.)

density

1.068 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CCOP(=O)(OCC)C=C

InChI

1S/C6H13O3P/c1-4-8-10(7,6-3)9-5-2/h6H,3-5H2,1-2H3

InChI key

DREPONDJUKIQLX-UHFFFAOYSA-N

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Application

Diethyl vinylphosphonate (DEVP) can be used as a precursor for the synthesis of:
  • 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.

wgk_germany

WGK 3

flash_point_f

230.0 °F

flash_point_c

110 °C

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

Certificates of Analysis (COA)

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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
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)
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)

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