Ethyl Vinyl Ether|CAS: 109-92-2

Ethyl Vinyl Ether (CAS: 109-92-2)

Basic Information:

- Chemical Name: Ethyl vinyl ether (EVE)

- Synonyms: Ethoxyethene, Vinyl ethyl ether

- CAS Number: 109-92-2

- Molecular Formula: C₄H₈O

- Molar Mass: 72.11 g/mol

- ASSAY:99%

- PH:7.0-8.0

Structure:

CH2=CH–O–CH₂CH₃ 

(An enol ether with a vinyl group attached to an ethoxy group)

Key Properties:

- Appearance: Colorless, highly volatile liquid

- Odor: Sweet, ether-like

- Boiling Point: ~35–36°C

- Flash Point: Below −30°C (highly flammable)

- Density: ~0.75 g/mL at 25°C

- Solubility: Slightly soluble in water, miscible with most organic solvents

Chemical Behavior:

- Highly flammable and forms explosive peroxides upon prolonged storage (requires inhibitor like KOH or BHT and testing before use).

- Reactivity: Undergoes typical electrophilic addition reactions due to the electron-rich double bond. 

- Hydrolysis: Readily cleaved by dilute acids to give acetaldehyde and ethanol. 

- Cycloadditions: Useful in [4+2] and [2+2] cycloadditions. 

- Protecting group: In organic synthesis, temporarily protects alcohols as vinyl ethers, which can be removed under mild acidic conditions.

- Polymerization: Can polymerize under acidic or radical conditions.

Main Applications:

1. Organic Synthesis: 

- Protecting group for alcohols and diols (acid-labile). 

- Precursor in the synthesis of other vinyl ethers and monomers. 

- Used in heterocyclic and natural product synthesis.

2. Industrial: 

- Monomer for specialty polymers/adhesives. 

- Intermediate for pharmaceuticals, fragrances, and dyes.

3. Former Use: Anesthetic (historically), but now largely replaced due to flammability risks.

Handling & Safety:

- Storage: Store under inert atmosphere (N₂/Ar) at 2–8°C, with added stabilizer. 

- Safety Notes: 

- Extremely flammable—keep away from ignition sources. 

- Peroxide formation risk—test before distillation or concentration. 

- Irritant to eyes, skin, and respiratory tract. 

- Use in well-ventilated areas or under a fume hood.

- Regulatory Status: Classified as flammable liquid (hazard class 3).

Key Takeaway: 

Ethyl vinyl ether is a versatile but hazardous enol ether, primarily used as a protecting group reagent and synthetic building block in organic chemistry, valued for its lability under mild acidic conditions.

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