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Merck
CN

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:
682-30-4
Molecular Weight:
164.14
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24847265
EC Number:
211-663-2
Beilstein/REAXYS Number:
507596
MDL number:
MFCD00009079

Key Documents

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Product Name

Diethyl vinylphosphonate, 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%

refractive index

n20/D 1.429 (lit.)

bp

202 °C (lit.)

density

1.068 g/mL at 25 °C (lit.)

functional group

phosphonate

storage temp.

2-8°C

Quality Level

100

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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.

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCV1865
MKCQ6449
MKCJ4345
MKCC1463
MKBW6440V

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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)
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)
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
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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