3',5'-Bis(trifluoromethyl)acetophenone
[CAS# 30071-93-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic acid
• Name: 3',5'-Bis(trifluoromethyl)acetophenone
• Synonyms: 1-[3,5-bis(trifluoromethyl)phenyl]ethanone
• Molecular Formula: C₁₀H₆F₆O
• Molecular Weight: 256.15
• CAS Registry Number: 30071-93-3
• EC Number: 250-023-7
• SMILES: CC(=O)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*,1.42 g/mL (Expl.)
• Index of Refraction: 1.407, Calc.^*, 1.4221 (Expl.)
• Boiling Point: 162.7±35.0 °C (760 mmHg), Calc.^*, 95-98 °C (15 mmHg) (Expl.)
• Flash Point: 82.2±0.0 °C, Calc.^*, 82 °C (Expl.)

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

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

Discovery and Applications

3',5'-Bis(trifluoromethyl)acetophenone, a chemical compound with the molecular formula C9H7F6O, is a substituted acetophenone derivative characterized by the presence of two trifluoromethyl groups at the para positions of the phenyl ring. This compound is part of a class of fluorinated organic compounds that have garnered significant attention due to their unique chemical properties, including enhanced lipophilicity and chemical stability. The trifluoromethyl group is a well-known electron-withdrawing group that imparts increased polarity and alters the reactivity of aromatic compounds, making them valuable intermediates in various chemical syntheses.

The discovery of 3',5'-bis(trifluoromethyl)acetophenone is attributed to ongoing efforts in fluorine chemistry, where scientists have explored the synthesis and reactivity of fluorinated organic compounds. The compound itself is likely derived from more general studies into the functionalization of acetophenone derivatives with electron-withdrawing groups to fine-tune their reactivity for specific synthetic applications. Its synthesis typically involves the introduction of trifluoromethyl groups into acetophenone through methods such as electrophilic aromatic substitution reactions, a common approach for incorporating highly reactive trifluoromethyl groups into aromatic systems.

One of the primary applications of 3',5'-bis(trifluoromethyl)acetophenone is in the synthesis of pharmaceuticals and agrochemicals. The trifluoromethyl groups increase the compound’s lipophilicity and metabolic stability, making it a useful building block for creating drug candidates with improved bioavailability. Fluorine atoms, particularly in the trifluoromethyl configuration, often modify the pharmacokinetic properties of organic molecules, including their ability to cross cell membranes and their metabolic stability. As a result, 3',5'-bis(trifluoromethyl)acetophenone has been investigated for its potential in designing compounds with enhanced activity and reduced degradation in biological systems.

In addition to pharmaceutical applications, this compound has also been studied in materials science, particularly in the development of new functional materials. The introduction of fluorine atoms, especially in the form of the trifluoromethyl group, often results in compounds with unique electronic properties, such as increased hydrophobicity and enhanced thermal stability. These characteristics are desirable in the design of advanced materials for applications in electronics, coatings, and even sensors. The compound’s increased chemical stability and reactivity also make it a useful intermediate in the synthesis of other complex fluorinated organic molecules that may have applications in advanced technologies.

Moreover, 3',5'-bis(trifluoromethyl)acetophenone has been explored in the context of agrochemical research, where fluorinated compounds are often introduced to modify the properties of active ingredients in pesticides, herbicides, and fungicides. The enhanced chemical stability and selectivity of fluorinated compounds can lead to more effective and environmentally friendly agrochemicals. The trifluoromethyl group in this acetophenone derivative could potentially improve the potency and durability of agrochemical agents, making them more efficient in agricultural applications while minimizing the environmental impact.

The compound also has potential in organic electronics, particularly in the development of organic light-emitting diodes (OLEDs) and organic photovoltaic devices. Fluorinated organic compounds like 3',5'-bis(trifluoromethyl)acetophenone have been investigated for their role in improving the efficiency, stability, and performance of such devices. The introduction of trifluoromethyl groups can enhance charge transport and electronic properties, making these materials suitable for use in high-performance optoelectronic applications.

In conclusion, 3',5'-bis(trifluoromethyl)acetophenone is a versatile and valuable chemical compound with applications spanning pharmaceuticals, agrochemicals, materials science, and organic electronics. The trifluoromethyl groups in its structure contribute to its enhanced stability, reactivity, and potential for use in various advanced technologies. Its discovery and continued exploration in synthetic chemistry offer a wealth of possibilities for developing new compounds with unique properties and applications across multiple fields.

References

2003. An Improved Preparation of 3,5-Bis(trifluoromethyl)acetophenone and Safety Considerations in the Preparation of 3,5-Bis(trifluoromethyl)phenyl Grignard Reagent. The Journal of Organic Chemistry, 68(10), 4120-4122.
DOI: 10.1021/jo026903n

2018. Development of an Efficient and Cost-Effective Enzymatic Process for Production of (R)-[3,5-bis(trifluoromethyl)phenyl] Ethanol Using Carbonyl Reductase Derived from Leifsonia sp. S749. Applied Biochemistry and Biotechnology, 187(3), 836-849.
DOI: 10.1007/s12010-018-2904-2

2019. BioTransformer: a comprehensive computational tool for small molecule metabolism prediction and metabolite identification. Journal of Cheminformatics, 11(2), 1-25.
DOI: 10.1186/s13321-018-0324-5