Ethyl trifluoroacetate
[CAS# 383-63-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Ethyl ester compound
• Name: Ethyl trifluoroacetate
• Synonyms: Ethyl 2,2,2-trifluoroacetate
• Molecular Formula: C₄H₅F₃O₂
• Molecular Weight: 142.08
• CAS Registry Number: 383-63-1
• EC Number: 206-851-6
• SMILES: CCOC(=O)C(F)(F)F

Properties

• Water solubility: Hydrolysis
• Density: 1.2±0.1 g/cm³, Calc.^*, 1.194 g/mL (Expl.)
• Melting point: -78 °C (Expl.)
• Index of Refraction: 1.322, Calc.^*, 1.3067 (Expl.)
• Boiling Point: 61.5±3.0 °C (760 mmHg), Calc.^*, 60-62 °C (Expl.)
• Flash Point: -1.1±0.0 °C, Calc.^*, -1 °C (Expl.)

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

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS07 Danger
• Risk Statements: H225-H302-H315-H318-H319-H335-H411
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	2	H225
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Serious eye damage	Eye Dam.	1	H318
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1B	H314

• Transport Information: UN 1993

Discovery and Applications

Ethyl trifluoroacetate is an organic compound with the chemical formula C4H5F3O2. It is an ester of trifluoroacetic acid and ethanol, and it belongs to the class of trifluoromethylated compounds. Trifluoromethylated esters, like ethyl trifluoroacetate, are known for their unique electronic properties, primarily derived from the electron-withdrawing nature of the trifluoromethyl group. These compounds have attracted considerable attention in various fields, particularly in organic synthesis and the pharmaceutical industry.

The discovery of ethyl trifluoroacetate can be traced back to the increasing interest in trifluoromethylated compounds in the mid-20th century. The trifluoromethyl group, due to its electron-withdrawing effect, enhances the reactivity and stability of molecules, making them valuable intermediates in synthetic chemistry. Ethyl trifluoroacetate is commonly used in organic synthesis as a versatile reagent and building block for the formation of various chemical compounds. Its utility is largely attributed to its ability to introduce the trifluoromethyl group into organic molecules, which can significantly alter the chemical and physical properties of the resultant compounds.

One of the key applications of ethyl trifluoroacetate is in the synthesis of pharmaceuticals. Trifluoromethylation is known to improve the bioavailability and metabolic stability of drug candidates. The trifluoromethyl group can enhance the lipophilicity of molecules, aiding their absorption and distribution within biological systems. Ethyl trifluoroacetate is often used as a precursor or reagent in the synthesis of biologically active compounds, including those with potential applications as anti-cancer agents, anti-inflammatory drugs, and enzyme inhibitors.

In addition to its pharmaceutical applications, ethyl trifluoroacetate is widely used in the preparation of agrochemicals and specialty chemicals. The trifluoromethyl group imparts resistance to chemical degradation, which can improve the stability and effectiveness of agrochemical agents. Moreover, ethyl trifluoroacetate is used in the synthesis of fluorinated polymers and other materials, where its properties are beneficial for enhancing performance characteristics, such as resistance to heat and chemicals.

Ethyl trifluoroacetate has also found applications in the field of analytical chemistry. It is used as a reagent in mass spectrometry for the derivatization of organic compounds, facilitating their detection and identification. Furthermore, it is employed in the preparation of fluoroalkylated products, which are useful in various chemical industries.

References

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