1-[3-Chloro-5-trifluoromethylphenyl]-2,2,2-trifluoroethanone
[CAS# 1125812-58-9]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluorobenzaldehyde series
• Name: 1-[3-Chloro-5-trifluoromethylphenyl]-2,2,2-trifluoroethanone
• Molecular Formula: C₉H₃ClF₆O
• Molecular Weight: 276.56
• CAS Registry Number: 1125812-58-9
• EC Number: 808-269-3
• SMILES: C1=C(C=C(C=C1C(F)(F)F)Cl)C(=O)C(F)(F)F

Properties

• Density: 1.512±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.424, Calc.^*
• Boiling Point: 203.0±40.0 °C (760 mmHg), Calc.^*
• Flash Point: 76.5±27.3 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H314
• Safety Statements: P260-P264-P270-P280-P301+P317-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P330-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

1-[3-Chloro-5-trifluoromethylphenyl]-2,2,2-trifluoroethanone is a synthetic compound widely studied for its role in pharmaceuticals and agrochemicals. The compound's structure consists of a trifluoromethyl-substituted aromatic ring with a chloro group in the meta position and a trifluoroethanone moiety, making it highly electrophilic and reactive. This combination of functional groups enhances the molecule’s stability and biological activity, particularly in inhibiting specific enzymatic processes.

The discovery of this compound emerged during research into fluoroaromatic ketones for use as intermediates in medicinal chemistry. Researchers recognized that introducing trifluoromethyl groups into aromatic ketones could significantly alter the physicochemical properties, such as increasing lipophilicity and metabolic stability. These modifications enable the compound to interact effectively with biological targets, including enzymes and receptors, while resisting metabolic degradation. Early synthetic efforts focused on refining halogenation patterns on the aromatic ring to optimize these effects.

1-[3-Chloro-5-trifluoromethylphenyl]-2,2,2-trifluoroethanone has proven valuable in pharmaceutical research as a core structure for developing enzyme inhibitors. The electron-withdrawing trifluoromethyl groups enhance the compound's ability to participate in hydrogen bonding and other molecular interactions, making it effective in binding to active sites of target enzymes. Studies have shown its potential in developing anti-inflammatory and antimicrobial agents due to its inhibitory effects on cyclooxygenases and bacterial enzymes.

In agrochemical applications, this compound serves as an intermediate in the synthesis of herbicides and fungicides. The structural features allow for the formulation of derivatives that inhibit essential plant or fungal metabolic pathways. The trifluoromethyl groups contribute to increased environmental stability and efficacy in field conditions. Additionally, the presence of the chloro substituent helps fine-tune the biological activity, enabling the selective targeting of pests while minimizing harm to crops.

The compound's synthetic versatility also makes it a valuable building block in material sciences. Researchers have utilized it to develop advanced polymers and liquid crystals due to its electron-withdrawing properties, which influence the electrical and optical characteristics of these materials. Its ability to form stable derivatives through various chemical transformations broadens its applicability across different scientific disciplines.

Ongoing research continues to explore the full potential of 1-[3-chloro-5-trifluoromethylphenyl]-2,2,2-trifluoroethanone in both pharmaceutical and agricultural fields. Efforts to optimize its derivatives aim to enhance efficacy, selectivity, and environmental compatibility. The compound’s discovery highlights the importance of fluorine chemistry in modern synthetic applications and its role in driving innovation in chemical design.

References

2019. List of PFAS identified in REACH 2019.
DOI: 10.5281/zenodo.7426856