4-Ethenylphenol acetate

Details:

4-Ethenylphenol acetate (also known as 4-vinylphenyl acetate or 4-acetoxystyrene) is an organic compound with the following structure and properties:

Chemical Structure & Nomenclature

• IUPAC Name: Acetic acid 4-ethenylphenyl ester

• Formula: C1010?H1010?O22?

• Structure: A benzene ring with:

  • A vinyl group (-CH=CH22?) at the para (4-) position.

  • An acetate ester (-OAc) replacing the hydroxyl group of phenol.

Key Characteristics

• Appearance: Typically a colorless to pale yellow liquid.

• Solubility: Likely soluble in organic solvents (e.g., ethanol, acetone) but poorly soluble in water.

• Reactivity:

  • The vinyl group enables polymerization (e.g., via free-radical or ionic mechanisms).

  • The acetate group acts as a protecting group for the phenolic hydroxyl, which can be deacetylated under acidic/basic conditions.

Applications

1. Polymer Chemistry:

   • Serves as a monomer for synthesizing functionalized polystyrene derivatives.

   • Used in specialty polymers for coatings, adhesives, or photoresists (e.g., in semiconductor manufacturing).

2. Organic Synthesis:

   • Intermediate for producing 4-vinylphenol (via hydrolysis of the acetate), which is used in resins and fragrances.

3. Flavor/Fragrance:

   • May contribute to aroma profiles in food or perfumes, as phenolic acetates are sometimes volatile odorants.

4. Biochemistry:

   • 4-Vinylphenol derivatives occur naturally in fermented products (e.g., wine, soy sauce) via decarboxylation of 4-hydroxycinnamic acid. The acetate form could act as a stabilized precursor.

Synthesis

• Common Route: Acetylation of 4-vinylphenol with acetic anhydride or acetyl chloride.

• Alternative: Functionalization of 4-hydroxystyrene (4-vinylphenol) with acetylating agents.

Safety & Handling

• Hazards:

  • May irritate skin/eyes.

  • Flammable due to the vinyl group.

• Storage: Keep in a cool, dry place away from oxidizers and ignition sources.

Regulatory & Commercial Status

• CAS Number: 2628-16-2 (for 4-acetoxystyrene).

• Industrial Use: Niche applications in polymer science; not widely commercialized for consumer products.

Key Notes

• Often confused with 4-hydroxystyrene (the deacetylated form, CAS 2628-17-3).

• The acetate group enhances stability during storage and handling compared to free phenolic compounds.

In summary, 4-ethenylphenol acetate is a specialized monomer and synthetic intermediate with applications in advanced materials and organic chemistry. Its utility stems from its dual functional groups (vinyl and acetate), enabling controlled polymerization and chemical modifications.