3',5'-Dichloro-2,2,2-trifluoroacetophenone
[CAS# 130336-16-2]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: 3',5'-Dichloro-2,2,2-trifluoroacetophenone
• Synonyms: 1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethanone; 1-(3',5'-Dichlorophenyl)-2,2,2-trifluoroethanone; 1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethanone
• Molecular Formula: C₈H₃Cl₂F₃O
• Molecular Weight: 243.01
• CAS Registry Number: 130336-16-2
• EC Number: 675-511-0
• SMILES: C1=C(C=C(C=C1Cl)Cl)C(=O)C(F)(F)F

Properties

• Density: 1.506±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.489, Calc.^*
• Boiling Point: 265.0±40.0 °C (760 mmHg), Calc.^*, 91-94 °C (12 mmHg) (Expl.)
• Flash Point: 114.0±27.3 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H302-H315-H319-H335-H411-H413
• Safety Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

3',5'-Dichloro-2,2,2-trifluoroacetophenone is an important chemical compound widely studied for its unique structure and potential applications in various fields. It belongs to the class of halogenated acetophenones, which are often investigated due to their chemical reactivity and biological activity. The compound features both chloro and trifluoro groups attached to the aromatic ring, which contribute to its distinctive chemical properties and its potential as a versatile building block in organic synthesis.

The discovery of 3',5'-Dichloro-2,2,2-trifluoroacetophenone is rooted in the continued exploration of halogenated aromatic compounds for their applications in pharmaceuticals, agrochemicals, and materials science. The combination of chlorine and fluorine atoms in the molecule enhances its electrophilic character, making it a valuable intermediate in the synthesis of more complex compounds. The trifluoromethyl group, in particular, is known for its ability to influence the biological activity of molecules by affecting their electronic properties and interaction with various biological targets.

One of the most significant applications of 3',5'-Dichloro-2,2,2-trifluoroacetophenone is in medicinal chemistry. The compound serves as a key intermediate in the synthesis of various bioactive molecules, including potential drugs targeting cancer, inflammation, and infectious diseases. The presence of halogen atoms in the structure increases the compound's lipophilicity, which can improve its ability to cross biological membranes and interact with cellular targets. Additionally, the compound has been explored for its ability to inhibit specific enzymes and modulate receptor activity, making it a candidate for the development of novel therapeutic agents.

Beyond pharmaceuticals, 3',5'-Dichloro-2,2,2-trifluoroacetophenone also finds use in agrochemical research, where it may be employed in the development of new pesticides and herbicides. The stability imparted by the trifluoroacetophenone backbone, combined with the electron-withdrawing effects of the chlorine and fluorine atoms, makes it a suitable candidate for designing compounds with enhanced activity and selectivity in agricultural applications.

The compound’s chemical structure and reactivity also make it a valuable tool in materials science. It has been explored as a precursor in the synthesis of polymeric materials with enhanced thermal stability and chemical resistance. The trifluoromethyl and chloro groups can impart specific properties to polymers, such as improved flame retardancy or resistance to environmental degradation.

Research into the synthesis and application of 3',5'-Dichloro-2,2,2-trifluoroacetophenone continues to grow, with an emphasis on fine-tuning its chemical properties to suit specific industrial and pharmaceutical needs. Further studies into its mechanism of action, particularly in biological systems, are expected to expand its range of applications and improve its therapeutic potential.

References

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