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Key Documents

422177

Sigma-Aldrich

Ethyl vinyl ether

contains 0.1% KOH as stabilizer, 99%

Sinônimo(s):

Ethoxyethylene

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About This Item

Fórmula linear:
C2H5OCH=CH2
Número CAS:
Peso molecular:
72.11
Beilstein:
605351
Número CE:
Número MDL:
Código UNSPSC:
12162002
eCl@ss:
39021025
ID de substância PubChem:
NACRES:
NA.23

Ensaio

99%

forma

liquid

contém

0.1% KOH as stabilizer
0.1% potassium hydroxide as stabilizer

índice de refração

n20/D 1.376 (lit.)

pb

33 °C (lit.)

pf

−116 °C (lit.)

densidade

0.753 g/mL at 25 °C (lit.)

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

CCOC=C

InChI

1S/C4H8O/c1-3-5-4-2/h3H,1,4H2,2H3

chave InChI

FJKIXWOMBXYWOQ-UHFFFAOYSA-N

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Descrição geral

Ethyl vinyl ether, also known as ethoxy ethane is highly reactive due to the presence of the vinyl group and the ether functionality. It can polymerize via different methods like radical polymerization, cationic polymerization, oroxidative polymerization, yielding poly(ethyl vinyl ether) or PVE. It is widely used as a monomer to synthesize copolymers and block polymers with thermal stability and flexibility for various applications such as the synthesis of silicone hydrogel for contact lenses, tissue engineering, 3D bioprinting, drug delivery, and Li-ion batteries.

Aplicação

Ethyl vinyl ether can be used as:


  • A monomer to synthesize amphiphilic block copolymers to fabricate protein-repelling polymersomes to produce spherical nanoparticles. These nanoparticles can be used as drug carriers.
  • A precursor to synthesize polymer electrolytes and cathode materials for solid-state lithium-ion batteries via UV photopolymerizations.
  • A monomer to synthesize poly(vinyl ether)s with controlled molecular weight and narrow dispersity via photoinduced free radical-promoted cationic reversible addition–fragmentation chain transfer (RAFT) polymerization. These polymers are used to fabricate 3D objects with different thicknesses by employing stereolithography-based 3D printing.

  • H-bonded Reusable Template Assisted para-Selective Ketonisation: This study discusses the use of ethyl vinyl ether in catalytic processes involving palladium and hexafluoroisopropanol to achieve para-selectivity in ketonisation, relevant for synthesizing complex organic compounds used in pharmaceuticals and materials science (A Maji, A Dahiya, G Lu, T Bhattacharya, 2018).

  • Mechanistic Insight into Photocontrolled Cationic Polymerization: Explores the photocontrolled polymerization of ethyl vinyl ether, providing valuable knowledge for the development of light-responsive materials, which could have applications in drug delivery and smart material systems (Q Michaudel, T Chauviré, V Kottisch, 2017).

Pictogramas

FlameExclamation mark

Palavra indicadora

Danger

Frases de perigo

Declarações de precaução

Classificações de perigo

Aquatic Chronic 3 - Flam. Liq. 2 - STOT SE 3

Órgãos-alvo

Central nervous system

Código de classe de armazenamento

3 - Flammable liquids

Classe de risco de água (WGK)

WGK 1

Ponto de fulgor (°F)

-49.0 °F

Ponto de fulgor (°C)

-45 °C

Equipamento de proteção individual

Eyeshields, Faceshields, Gloves


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O Schalk et al.
The journal of physical chemistry. A, 119(45), 11105-11112 (2015-10-23)
A series of different alkyl vinyl ethers is investigated to decipher the possible reaction channels upon photoexcitation to the π3s-Rydberg and the ππ*-valence state at 200 nm using time-resolved photoelectron spectroscopy and on-the-fly time-dependent density functional theory dynamics simulations. The
Laurance G Beauvais et al.
Journal of the American Chemical Society, 127(20), 7370-7378 (2005-05-19)
Soluble methane monooxygenase (sMMO) isolated from Methylococcus capsulatus (Bath) utilizes a carboxylate-bridged diiron center and dioxygen to catalyze the conversion of methane to methanol. Previous studies revealed that a di(mu-oxo)diiron(IV) intermediate termed Q is responsible for the catalytic activity with
Eden Tesfu et al.
Journal of the American Chemical Society, 128(1), 70-71 (2006-01-05)
A Pd(II) reagent has been generated at preselected sites on an electrochemically addressable chip and used to effect the oxidation of the neighboring alcohols on the polymer coating the chip's surface. The resulting carbonyls were then used to accomplish site-selective
Guotao Li et al.
Journal of the American Chemical Society, 130(22), 6944-6945 (2008-05-10)
An efficient Au(I)-catalyzed synthesis of highly strained and functionalized bicyclo[3.2.0]heptanes is developed. Subsequent couplings with various nucleophiles offer additional structural features/complexity. These one-pot, three-component reactions are proposed to proceed via a key 1,3-dipolar cycloaddition between a Au carbenoid-containing carbonyl ylide
Natalia Chernyak et al.
Journal of the American Chemical Society, 134(30), 12466-12469 (2012-07-21)
Anilines and ethyl vinyl ether can be used as precursors for a process that is the synthetic equivalent of the α-arylation of acetaldehyde enolate. The reaction manifests a high level of functional group compatibility, allowing the ready preparation of a

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