2,2,2-Trifluoroethyl acetate
[CAS# 406-95-1]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: 2,2,2-Trifluoroethyl acetate
• Synonyms: Trifluoroethyl acetate
• Molecular Formula: C₄H₅F₃O₂
• Molecular Weight: 142.08
• CAS Registry Number: 406-95-1
• EC Number: 671-427-3
• SMILES: CC(=O)OCC(F)(F)F

Properties

• Solubility: Sparingly soluble (16 g/L) (25 ºC), Calc.^*
• Density: 1.32058 g/cm³ (16 ºC)^**
• Boiling point: 78 ºC^***
• Refractive index: 1.3273 (16 ºC)^**
• Flash point: -23.6±19.6 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

^** Swarts, Fred.; Compt. rend. 1933, V197, P1261-4.

^*** Henne, Albert L.; Journal of the American Chemical Society 1952, V74, P1426-8.

Safety Data

• Hazard Symbols: GHS02;GHS07 Danger
• Hazard Statements: H225-H315-H319
• Precautionary Statements: P210-P233-P240-P241-P242-P243-P264-P264+P265-P280-P302+P352-P303+P361+P353-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364-P370+P378-P403+P235-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	2	H225
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

2,2,2-Trifluoroethyl acetate (C₄HF₃O₂) is a fluorinated organic compound that features both an ester group and a trifluoroethyl group. It is primarily used as a chemical reagent and intermediate in various organic synthesis reactions. The presence of the trifluoroethyl group imparts unique reactivity and properties to this compound, making it valuable in several industrial applications.

The discovery and development of 2,2,2-trifluoroethyl acetate are linked to the growing interest in organofluorine chemistry. Organofluorine compounds are important in many industries, particularly pharmaceuticals, agrochemicals, and materials science, because the introduction of fluorine atoms into organic molecules often results in improved chemical stability, biological activity, and lipophilicity. The trifluoroethyl group is known for its electron-withdrawing effects, which can influence the reactivity of nearby functional groups in a predictable manner, making it a useful building block in chemical synthesis.

In synthetic chemistry, 2,2,2-trifluoroethyl acetate serves as an intermediate for the preparation of various fluorinated compounds. It is commonly used in the synthesis of fluorinated carboxylic acids, alcohols, and other fluorinated derivatives. The compound can also be employed as a source of the trifluoroethyl group, which can be transferred to other molecules in reactions such as nucleophilic substitution or electrophilic addition. These reactions are useful for the development of novel materials and compounds with specific properties that are desirable in various industrial applications.

One of the key areas where 2,2,2-trifluoroethyl acetate finds application is in the pharmaceutical industry. Fluorinated compounds, including those containing the trifluoroethyl group, are of significant interest in drug design because the presence of fluorine can enhance the biological activity, stability, and metabolic profile of a drug. The trifluoroethyl group can improve the pharmacokinetics of pharmaceutical agents, including their absorption, distribution, metabolism, and excretion properties. This is particularly important in the development of drugs with improved efficacy and reduced side effects. As a result, 2,2,2-trifluoroethyl acetate and its derivatives are often used in the synthesis of fluorinated pharmaceuticals.

In addition to its use in pharmaceuticals, 2,2,2-trifluoroethyl acetate is employed in the agrochemical industry. Fluorinated agrochemicals, such as herbicides, fungicides, and insecticides, benefit from the enhanced chemical stability and persistence imparted by the trifluoroethyl group. The introduction of fluorine atoms can also improve the effectiveness of these chemicals, allowing them to remain active for longer periods and reducing the frequency of application. Fluorinated agrochemicals are crucial in modern agriculture for controlling pests and diseases while ensuring better crop yields.

2,2,2-Trifluoroethyl acetate also finds applications in the production of fluorinated polymers and materials. The trifluoroethyl group imparts excellent chemical resistance, thermal stability, and mechanical properties to the resulting polymers. These fluorinated polymers are used in a wide range of applications, including coatings, adhesives, and sealants, where durability and resistance to harsh environments are required. The unique properties of these materials make them suitable for industries such as aerospace, automotive, and electronics, where high-performance materials are essential.

Another area of application for 2,2,2-trifluoroethyl acetate is in the development of specialty solvents. The trifluoroethyl group enhances the solvent's ability to dissolve a variety of organic and inorganic compounds, and the acetate functionality allows for the formation of esters with other molecules, making it useful in the formulation of solvents for various chemical processes.

Despite its many applications, the use of 2,2,2-trifluoroethyl acetate must be managed with care due to the environmental impact of fluorinated compounds. Fluorinated chemicals are known to be persistent in the environment, and their accumulation can lead to environmental contamination. As such, research efforts are ongoing to develop more sustainable and environmentally friendly methods for the production and disposal of fluorinated compounds like 2,2,2-trifluoroethyl acetate.

In summary, 2,2,2-trifluoroethyl acetate is a versatile and valuable compound in the fields of organic synthesis, pharmaceuticals, agrochemicals, and materials science. Its unique trifluoroethyl group provides desirable properties such as increased chemical stability and biological activity, making it useful for the development of new drugs, agrochemicals, and specialty materials. While its applications are widespread, the environmental impact of fluorinated compounds remains an important consideration in their use and disposal.

References

2021. Improved stability of highly concentrated LiBF4/fluorinated ethyl acetate-based electrolyte solutions with a co-solvent for LiNi0.8Co0.1Mn0.1O2 positive electrodes in lithium ion batteries. Journal of Applied Electrochemistry, 51(9).
DOI: 10.1007/s10800-021-01590-w

2016. Identification of solid electrolyte interphase formed on graphite electrode cycled in trifluoroethyl aliphatic carboxylate-based electrolytes for low-temperature lithium-ion batteries. Ionics, 22(10).
DOI: 10.1007/s11581-016-1743-9

2013. Selective acylation of the phenolic hydroxyl of (hydroxyalkyl)phenols by using vinyl carboxylates as acyl donors in the presence of rubidium fluoride. Monatshefte für Chemie - Chemical Monthly, 144(9).
DOI: 10.1007/s00706-013-1019-2