Acetonylacetone
[CAS# 110-13-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty ketone (including enol)
• Name: Acetonylacetone
• Synonyms: 2,5-Hexanedione
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.14
• CAS Registry Number: 110-13-4
• EC Number: 203-738-3
• SMILES: CC(=O)CCC(=O)C

Properties

• Solubility: 1.791e+005 mg/L (25 ºC water)
• Density: 0.973 g/cm³
• Index of Refraction: 1.406, Calc.^*, 1.425-1.427
• Melting point: -17.32 ºC, -6 ºC
• Boiling Point: 188.8±13.0 ºC (760 mmHg), Calc.^*, 162.59 ºC, 185-193 ºC
• Flash Point: 78.9±0.0 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Hazard Statements: H315-H319-H373
• Precautionary Statements: P260-P264-P264+P265-P280-P302+P352-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute toxicity	Acute Tox.	4	H302
Reproductive toxicity	Repr.	2	H361
Acute toxicity	Acute Tox.	3	H331
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Reproductive toxicity	Repr.	2	H361f

Discovory and Applicatios

Acetonylacetone, also known as 2,4-Hexanedione, was first discovered in the late 19th century through organic synthesis methods. Acetonylacetone's unique structure, characterized by two ketone groups separated by a methylene bridge, intrigued researchers and sparked interest in exploring its chemical reactivity and potential applications.

Acetonylacetone serves as a valuable building block in organic synthesis, serving as a precursor for the preparation of various organic compounds, including pharmaceuticals, agrochemicals, and fine chemicals. Acetonylacetone exhibits chelating properties, allowing it to form stable complexes with metal ions such as copper, nickel, and iron. These metal complexes find applications in catalysis, metal extraction, and analytical chemistry, where they serve as catalysts, reagents, and analytical probes in various chemical reactions and processes.Acetonylacetone is utilized in the flavor and fragrance industry as a key ingredient in the synthesis of aroma compounds, flavor enhancers, and fragrance ingredients. Its pleasant odor and low volatility make it suitable for imparting fruity, floral, and sweet notes to perfumes, cosmetics, and food products. Acetonylacetone participates in polymerization reactions, particularly in the synthesis of polymers and copolymers with desirable properties for industrial applications. Its reactivity and functionality enable the formation of crosslinked networks. Acetonylacetone finds applications in the production of photographic chemicals, where it serves as a reagent for silver complexation and photographic emulsion sensitization. Its ability to form stable complexes with silver ions enhances the sensitivity and resolution of photographic films and papers. Acetonylacetone is employed as a reagent and indicator in various analytical methods, including spectrophotometry, chromatography, and titration. Acetonylacetone is used in art conservation and restoration as a cleaning agent for the removal of varnishes, coatings, and contaminants from paintings, sculptures, and artifacts. Its solvency and mildness make it suitable for delicate cleaning procedures, preserving the integrity and aesthetics of cultural heritage objects.

References

2024. Pyrrole adducts mediated mitochondrial dysfunction activates SARM1-dependent axon degeneration in 2,5-hexanedione-induced neuropathy. Environmental pollution (Barking, Essex : 1987), 360.
DOI: 10.1016/j.envpol.2024.124651

2024. Humin-sulfuric acid as a novel recoverable biocatalyst for pyrrole synthesis in water. BMC Chemistry, 18(1).
DOI: 10.1186/s13065-024-01269-1

2024. Elevating pyrrole derivative synthesis: a three-component revolution. Molecular Diversity, 28(5).
DOI: 10.1007/s11030-024-10884-y