2,2,2-Trifluoroethyl Acetate: Uses, Properties & FAQs

2,2,2-Trifluoroethyl Acetate is a fluorinated ester reagent widely used in organic synthesis as an activated acyl-transfer agent and specialty solvent, offering enhanced electrophilicity compared with conventional esters due to the electron-withdrawing trifluoroethyl group.

Chemical Name

2,2,2-Trifluoroethyl Acetate

Molecular Formula

C₄H₅F₃O₂

Molecular Weight

128.08 g/mol

CAS Number

406-95-1

Aladdin SKU

T405032

Reference Source

TCI T3422

Appearance

Colorless liquid

Key Application

Activated acylation and transesterification reactions in organic synthesis

What Is 2,2,2-Trifluoroethyl Acetate?

2,2,2-Trifluoroethyl Acetate (CAS 406-95-1; Aladdin SKU T405032) is the ester formed from acetic acid and 2,2,2-trifluoroethanol. The three fluorine atoms on the ethyl portion create a strong electron-withdrawing effect that makes the carbonyl carbon significantly more electrophilic than in simple alkyl acetates such as ethyl acetate or methyl acetate. This elevated electrophilicity translates directly into higher reactivity toward nucleophiles, making the compound a valuable activated acylating agent in both academic and industrial research settings. It is a colorless, low-viscosity liquid with a molecular weight of 128.08 g/mol and molecular formula C₄H₅F₃O₂.

Key Applications in Organic Synthesis

2,2,2-Trifluoroethyl Acetate serves several important roles in synthetic chemistry:

• Activated acylation: Because the 2,2,2-trifluoroethoxy leaving group is a better leaving group than simple alkoxy groups, the reagent efficiently acetylates amines, alcohols, and thiols under mild conditions, often without requiring a strong base or coupling reagent.
• Transesterification: The activated ester undergoes transesterification more readily than conventional acetates, facilitating the preparation of other esters under mild conditions.
• Green chemistry applications: Its reactivity profile can reduce the need for harsher acylating agents such as acetic anhydride or acetyl chloride, which may simplify workup and improve safety profiles in certain workflows.
• Synthesis of fluorinated intermediates: As a fluorine-containing building block, it can contribute to the preparation of fluorinated compounds of pharmaceutical or agrochemical interest.

Researchers should verify specific reaction conditions in the primary literature before use, as yields and selectivities are substrate-dependent.

Handling, Storage, and Safety

As with all reactive fluorinated esters, appropriate laboratory precautions are essential when working with 2,2,2-Trifluoroethyl Acetate:

• Personal protective equipment: Wear chemical-resistant gloves, safety goggles, and a lab coat. Work in a well-ventilated fume hood.
• Storage: Store in a tightly sealed container in a cool, dry, well-ventilated location away from moisture, strong bases, and oxidizing agents. Refrigerated storage is typically recommended to maintain stability.
• Stability: The compound is susceptible to hydrolysis in the presence of water, particularly under basic conditions; keep containers sealed when not in use.
• Disposal: Dispose of according to local, regional, and national regulations governing fluorinated organic waste.

Always consult the current Safety Data Sheet (SDS) provided by Aladdin Scientific before use. Specific hazard classifications, GHS pictograms, and first-aid measures are detailed therein.

Ordering and Specifications at Aladdin Scientific

Aladdin Scientific offers 2,2,2-Trifluoroethyl Acetate under SKU T405032, sourced with reference to TCI catalogue number T3422. When placing an order or evaluating the product for your research, consider the following:

• Purity: Confirm the purity specification on the current product page or Certificate of Analysis (CoA) before use in sensitive applications. Flag any purity requirements exceeding standard grades to our technical team.
• Pack sizes: Available pack sizes may vary; contact Aladdin customer service for bulk or custom quantity inquiries.
• Lead time: Standard stock items typically ship promptly; check the product page for real-time availability.
• Documentation: CoA, SDS, and structural confirmation data are available on request or via the product detail page.

For technical questions about suitability for a specific application, contact Aladdin Scientific's technical support team.

Frequently Asked Questions Overview

The FAQs below address the most common queries received from researchers and procurement teams regarding 2,2,2-Trifluoroethyl Acetate. Topics include chemical reactivity, comparison with alternative acylating agents, stability, and ordering logistics. If your question is not addressed here, please contact Aladdin Scientific customer support for personalized assistance.

Frequently asked questions

What makes 2,2,2-Trifluoroethyl Acetate more reactive than ethyl acetate?

The three fluorine atoms on the 2,2,2-trifluoroethyl group are strongly electron-withdrawing, which increases the electrophilicity of the carbonyl carbon and makes the trifluoroethoxy moiety a better leaving group than the ethoxy group in ethyl acetate. This results in faster and more complete acylation reactions under milder conditions.

Can 2,2,2-Trifluoroethyl Acetate be used as a direct replacement for acetic anhydride?

In many N-acetylation and O-acetylation reactions, 2,2,2-Trifluoroethyl Acetate can serve as a milder alternative to acetic anhydride, offering easier handling and a simpler byproduct profile (2,2,2-trifluoroethanol rather than acetic acid). However, it may not be a drop-in replacement in all protocols, and reaction conditions should be optimized for each specific substrate. Consult the primary literature or contact Aladdin's technical team for guidance.

How should 2,2,2-Trifluoroethyl Acetate be stored to ensure long-term stability?

Store 2,2,2-Trifluoroethyl Acetate in a tightly sealed container under cool, dry conditions, preferably refrigerated and protected from moisture. Exposure to water or aqueous base will promote hydrolysis. Always check the SDS and CoA for the recommended storage temperature and shelf-life information specific to your lot.

What purity grade is available for T405032 at Aladdin Scientific?

Purity specifications for SKU T405032 are detailed on the Aladdin Scientific product page and accompanying Certificate of Analysis. We recommend downloading the current CoA from the website or contacting customer service for the most up-to-date purity data for your specific lot.

Is 2,2,2-Trifluoroethyl Acetate suitable for pharmaceutical synthesis applications?

2,2,2-Trifluoroethyl Acetate is used in research-scale organic synthesis, including in routes toward pharmaceutical intermediates, owing to its mild and selective acylating properties. Suitability for GMP or regulated pharmaceutical manufacturing depends on additional quality and regulatory requirements beyond the research-grade specifications offered by Aladdin Scientific; consult your regulatory team for such applications.

What byproduct is generated when 2,2,2-Trifluoroethyl Acetate reacts with an amine?

When 2,2,2-Trifluoroethyl Acetate acylates an amine, the primary products are the corresponding acetamide and 2,2,2-trifluoroethanol. 2,2,2-Trifluoroethanol is relatively easy to remove by evaporation or aqueous workup given its volatility and water miscibility, which can simplify purification compared with reactions that generate less volatile byproducts.

References

1. TCI Chemicals catalogue entry T3422: 2,2,2-Trifluoroethyl Acetate. Tokyo Chemical Industry Co., Ltd.
2. Aladdin Scientific product page SKU T405032: 2,2,2-Trifluoroethyl Acetate.
3. General reference: Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, Part A: Structure and Mechanisms. Springer. [Chapter on ester reactivity and acyl transfer]

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