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116130

Sigma-Aldrich

Diethyl vinylphosphonate

97%

Sinônimo(s):

Vinylphosphonic acid diethyl ester

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About This Item

Fórmula linear:
CH2=CHPO(OCH2CH3)2
Número CAS:
682-30-4
Peso molecular:
164.14
Beilstein:
507596
Número CE:
211-663-2
Número MDL:
MFCD00009079
Código UNSPSC:
12352100
ID de substância PubChem:
24847265
NACRES:
NA.22

Ensaio

97%

índice de refração

n20/D 1.429 (lit.)

pb

202 °C (lit.)

densidade

1.068 g/mL at 25 °C (lit.)

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

CCOP(=O)(OCC)C=C

InChI

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

chave InChI

DREPONDJUKIQLX-UHFFFAOYSA-N

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Aplicação

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.

Código de classe de armazenamento

10 - Combustible liquids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

230.0 °F - closed cup

Ponto de fulgor (°C)

110 °C - closed cup

Equipamento de proteção individual

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

Certificados de análise (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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