1,1,1-Trifluoro-5-methylhexane-2,4-dione
[CAS# 30984-28-2]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: 1,1,1-Trifluoro-5-methylhexane-2,4-dione
• Synonyms: 5-Methyl-1,1,1-trifluoro-2,4-hexanedione
• Molecular Formula: C₇H₉F₃O₂
• Molecular Weight: 182.14
• CAS Registry Number: 30984-28-2
• EC Number: 250-415-8
• SMILES: CC(C)C(=O)CC(=O)C(F)(F)F

Properties

• Solubility: 3587 mg/L (25 ºC water)
• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.369, Calc.^*
• Melting point: -19.04 ºC
• Boiling Point: 160.9±35.0 ºC (760 mmHg), Calc.^*, 155.91 ºC
• Flash Point: 47.2±22.8 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS02;GHS07 Warning
• Hazard Statements: H226-H315-H319-H335
• Precautionary Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P271-P280-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Flammable liquids	Flam. Liq.	3	H226
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

1,1,1-Trifluoro-5-methylhexane-2,4-dione is a fluorinated β-diketone that has been studied as part of the broader development of organofluorine compounds for synthetic and analytical applications. The compound features a 1,1,1-trifluoromethyl group at the terminal carbon and keto groups at the 2- and 4-positions of a six-carbon chain, with a methyl substituent at the 5-position. The introduction of the trifluoromethyl group strongly influences the electronic properties of the molecule, enhancing the acidity of adjacent protons and stabilizing enolate intermediates. The β-diketone structure, combined with fluorination, makes the compound a versatile ligand for coordination chemistry and a useful intermediate in organic synthesis.

The discovery of 1,1,1-trifluoro-5-methylhexane-2,4-dione is associated with research into fluorinated diketones, which began in the mid-20th century as chemists explored the effects of fluorine on reactivity and stability. Fluorinated β-diketones were recognized for their ability to form stable chelates with metals, influencing catalytic activity, material properties, and biological interactions. The trifluoromethyl group not only increases the electron-withdrawing capacity of the molecule but also enhances its thermal and chemical stability compared with non-fluorinated analogues.

Applications of 1,1,1-trifluoro-5-methylhexane-2,4-dione are primarily in coordination chemistry and organic synthesis. The compound acts as a chelating ligand, forming complexes with transition metals such as copper, nickel, and lanthanides. These metal complexes have been studied for catalytic applications, including oxidation and polymerization reactions, where the electronic effects of the trifluoromethyl group can modulate activity and selectivity. Additionally, the β-diketone moiety allows for condensation reactions, enabling the synthesis of heterocyclic compounds such as pyrazoles, pyrimidines, and other nitrogen-containing rings. Such reactions are valuable in medicinal chemistry and material science for constructing functionalized heterocycles with fluorinated substituents.

In analytical chemistry, fluorinated β-diketones, including 1,1,1-trifluoro-5-methylhexane-2,4-dione, have been employed in metal ion extraction and separation. The formation of strong metal-chelate complexes allows for selective extraction of lanthanides and actinides in solvent systems, which has implications in nuclear chemistry and environmental analysis. The trifluoromethyl group enhances the lipophilicity of the resulting complexes, improving their solubility in organic solvents and facilitating efficient phase transfer.

The compound has also been explored as a precursor in the synthesis of fluorinated fine chemicals and specialty materials. The combination of β-diketone reactivity and trifluoromethyl stabilization allows for selective functionalization, including alkylation, acylation, and cyclization reactions. This makes it a useful intermediate in designing molecules with tailored electronic, steric, and solubility properties, which are important in pharmaceuticals, agrochemicals, and advanced materials.

The development and application of 1,1,1-trifluoro-5-methylhexane-2,4-dione highlight the broader role of fluorinated β-diketones in modern chemistry. By providing a stable, reactive platform for metal coordination and organic synthesis, this compound illustrates how the incorporation of trifluoromethyl groups can enhance chemical versatility, influence reactivity, and expand the toolkit available for researchers in synthetic, materials, and analytical chemistry.

References

2020. Upconversion Nanoparticles: Synthesis, Photoluminescence Properties, and Applications. Nanotechnologies in Russia, 15(6).
DOI: 10.1134/s1995078020060117

2004. Reaction with O-Methyluronium Salts. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-016-00527