Acetylacetone
Acetylacetone
Blog Article
Acetylacetone (2,4-Pentanedione): Structure, Properties, and Applications
Acetylacetone, also known as 2,4-Pentanedione, is an organic compound with the chemical formula C₅H₈O₂. It is a key reagent in coordination chemistry, organic synthesis, and industrial applications. Acetylacetone exists in equilibrium between its keto and enol forms, making it a versatile compound in various chemical reactions.
Chemical Structure and Formula
- Molecular Formula: C₅H₈O₂
- IUPAC Name: 2,4-Pentanedione
- Structure: CH₃-CO-CH₂-CO-CH₃
- Molecular Weight: 100.12 g/mol
- Functional Groups: Keto and enol groups
Tautomerism: Keto-Enol Equilibrium
Acetylacetone exists in two tautomeric forms:
- Keto Form: CH₃-CO-CH₂-CO-CH₃ (dominates in non-polar solvents)
- Enol Form: CH₃-C(OH)=CH-CO-CH₃ (stabilized by intramolecular hydrogen bonding)
In solution, a dynamic equilibrium exists between these forms, with the enol form being more stable due to hydrogen bonding.
Physical Properties : Acetylacetone
- Appearance: Colorless to pale yellow liquid
- Odor: Mild, characteristic odor
- Boiling Point: ~140°C
- Density: 0.975 g/cm³
- Solubility: Miscible with water, ethanol, and most organic solvents
Chemical Properties : Acetylacetone
- Acidic Nature:
- The enol form has an acidic hydrogen, allowing acetylacetone to act as a weak acid.
- Chelation Ability:
- Forms stable metal chelates with transition metals like Fe³⁺, Co²⁺, and Cu²⁺.
- Reactivity in Organic Synthesis:
- Can undergo condensation reactions to form heterocycles.
- Used in Michael additions and aldol condensations.
Applications of Acetylacetone
- Metal Chelation:
- Used to synthesize metal-acetylacetonate complexes in catalysis and material science.
- Solvent and Intermediate:
- Used as a solvent and precursor in pharmaceuticals, agrochemicals, and coatings.
- Organic Synthesis:
- Used in the synthesis of heterocyclic compounds and bioactive molecules.
- Analytical Chemistry:
- Forms colored complexes for spectroscopic analysis of metal ions.
Safety and Handling : 2,4-Pentanedione
- Flammability: Highly flammable, handle with care.
- Toxicity: Can cause skin and eye irritation; should be handled with gloves and goggles.
- Storage: Store in a cool, dry place away from heat sources.
Conclusion
Acetylacetone is a versatile organic compound with significant applications in coordination chemistry, industrial manufacturing, and organic synthesis. Its unique tautomeric behavior and metal-chelating properties make it an essential reagent in scientific research and industrial processes.
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