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422177

Sigma-Aldrich

Ethyl vinyl ether

contains 0.1% KOH as stabilizer, 99%

Synonym(s):

Ethoxyethylene

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About This Item

Linear Formula:
C2H5OCH=CH2
CAS Number:
109-92-2
Molecular Weight:
72.11
Beilstein:
605351
EC Number:
203-718-4
MDL number:
MFCD00009248
UNSPSC Code:
12162002
eCl@ss:
39021025
PubChem Substance ID:
24866417
NACRES:
NA.23
Pricing and availability is not currently available.

Assay

99%

form

liquid

contains

0.1% KOH as stabilizer
0.1% potassium hydroxide as stabilizer

refractive index

n20/D 1.376 (lit.)

bp

33 °C (lit.)

mp

−116 °C (lit.)

density

0.753 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CCOC=C

InChI

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

InChI key

FJKIXWOMBXYWOQ-UHFFFAOYSA-N

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General description

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.

Application

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.[1]
  • A precursor to synthesize polymer electrolytes and cathode materials for solid-state lithium-ion batteries via UV photopolymerizations.[2]
  • 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).

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H336,H412

Hazard Classifications

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

Target Organs

Central nervous system

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

-49.0 °F

Flash Point(C)

-45 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB0534
STBL1303
STBK6710
STBK9357
STBK0546

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Polyglycidol-stabilized nanoparticles as a promising alternative to nanoparticle PEGylation: polymer synthesis and protein fouling considerations
Haiqin Du, et al.
Langmuir, 36, 1266-1278 (2020)
A PROXYL-Type Norbornene Polymer for High-Voltage Cathodes in Lithium Batteries
Hatakeyama-Sato, et al.
Macromolecular Rapid Communications, 42, 2100374-2100374 (2021)
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
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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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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