5,5,5-Trifluoro-4-hydroxy-4-(trifluoromethyl)-2-pentanone
[CAS# 10487-10-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Ketones
• Name: 5,5,5-Trifluoro-4-hydroxy-4-(trifluoromethyl)-2-pentanone
• Synonyms: 1,1,1-Trifluoro-2-hydroxy-2-(trifluoromethyl)pentan-4-one
• Molecular Formula: C₆H₆F₆O₂
• Molecular Weight: 224.10
• CAS Registry Number: 10487-10-2
• SMILES: CC(=O)CC(C(F)(F)F)(C(F)(F)F)O

Properties

• Density: 1.445
• Boiling point: 195 ºC
• Refractive index: 1.3430
• Flash point: 71 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H320-H335
• Precautionary Statements: P264-P270-P301+P312-P330

Discovory and Applicatios

5,5,5-Trifluoro-4-hydroxy-4-(trifluoromethyl)-2-pentanone is a synthetic compound with a unique structure containing multiple trifluoromethyl groups and one hydroxyl group on the pentanone backbone. It is a colorless to pale yellow liquid or crystalline solid that is *soluble in common organic solvents such as acetone, methanol, and dichloromethane. It combines the electron-withdrawing effect of the trifluoromethyl group with the reactivity of the hydroxyl and keto groups. It exhibits high chemical stability and unique reactivity due to the presence of the fluorine atom.

The synthesis of fluorinated ketones such as 5,5,5-trifluoro-4-hydroxy-4-(trifluoromethyl)-2-pentanone is part of an ongoing effort to explore the role of fluorine in organic chemistry. Since the mid-20th century, fluorinated compounds have attracted much attention for their enhanced chemical properties. The specific synthesis of this compound was developed in the late 20th century as part of research in organofluorine chemistry to exploit the unique reactivity and stability imparted by fluorine.

5,5,5-Trifluoro-4-hydroxy-4-(trifluoromethyl)-2-pentanone serves as a versatile building block for the synthesis of more complex fluorinated molecules. Its structure allows for a variety of chemical transformations that facilitate the introduction of trifluoromethyl groups into organic molecules, a common strategy to enhance the biological activity, lipophilicity, and metabolic stability of compounds.

5,5,5-Trifluoro-4-hydroxy-4-(trifluoromethyl)-2-pentanone is used in the design of new pharmaceutical agents. The presence of fluorine improves the properties of the drug, such as potency, selectivity, and bioavailability. The framework of this compound can be adjusted to create novel therapeutics with enhanced activity against biological targets. 5,5,5-Trifluoro-4-hydroxy-4-(trifluoromethyl)-2-pentanone can enhance the metabolic stability of potential drug candidates. The trifluoromethyl group can prevent enzymatic degradation, extending the half-life and efficacy of the drug.

5,5,5-Trifluoro-4-hydroxy-4-(trifluoromethyl)-2-pentanone is used in the development of fluorinated polymers and materials. These materials have unique properties, such as high thermal stability, chemical resistance, and low surface energy, making them suitable for advanced coatings and specialty plastics. 5,5,5-Trifluoro-4-hydroxy-4-(trifluoromethyl)-2-pentanone facilitates the synthesis of high-performance materials for electronics, optics, and other cutting-edge technologies, where stability and resistance to environmental factors are critical.

5,5,5-Trifluoro-4-hydroxy-4-(trifluoromethyl)-2-pentanone serves as a model compound when studying the reactivity and properties of fluorinated ketones. Studying its behavior helps understand the broad effects of fluorination in organic molecules and guides the design of new functional materials and drugs. 5,5,5-Trifluoro-4-hydroxy-4-(trifluoromethyl)-2-pentanone is used for mechanistic studies of organic reactions, providing insights into how fluorine substitution affects reaction pathways and product formation.

5,5,5-Trifluoro-4-hydroxy-4-(trifluoromethyl)-2-pentanone is used to explore the development of fluorinated agrochemicals, including herbicides and pesticides. Fluorination enhances the activity and selectivity of these compounds, thereby improving their effectiveness and environmental profile.