2,2,2-Trifluoro-N,N-dimethylacetamide
[CAS# 1547-87-1]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: 2,2,2-Trifluoro-N,N-dimethylacetamide
• Molecular Formula: C₄H₆F₃NO
• Molecular Weight: 141.09
• CAS Registry Number: 1547-87-1
• EC Number: 671-651-1
• SMILES: CN(C)C(=O)C(F)(F)F

Properties

• Solubility: 2.716e+004 mg/L (25 ºC water)
• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.350, Calc.^*
• Melting point: -31.06 ºC
• Boiling Point: 122.12 ºC, 133.0±0.0 ºC (760 mmHg), Calc.^*
• Flash Point: 36.7±25.9 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS02;GHS07 Danger
• Hazard Statements: H225-H315-H319
• Precautionary Statements: P210-P233-P240-P241+P242+P243-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P403+P235-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
Flammable liquids	Flam. Liq.	3	H226
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

2,2,2-Trifluoro-N,N-dimethylacetamide is a small organofluorine compound that belongs to the class of trifluoromethyl-substituted amides. Its discovery is closely linked to the mid-20th century expansion of fluorine chemistry, when chemists were systematically introducing trifluoromethyl groups into organic molecules to study their effects on chemical reactivity and physical properties. The incorporation of three fluorine atoms into the acetamide backbone results in a strongly electron-withdrawing substituent that alters the acidity, stability, and lipophilicity of the molecule. The dimethylamino substituent contributes further to the compound’s stability and solubility, making it suitable for use as a reagent and solvent in specialized chemical processes.

The compound has been investigated for its utility as a polar aprotic solvent. The presence of the trifluoromethyl group increases both its dielectric properties and resistance to oxidation, while the amide functionality allows it to dissolve a broad range of polar and nonpolar substances. These qualities make 2,2,2-trifluoro-N,N-dimethylacetamide useful in laboratory settings where high chemical stability is required. Although less common than other solvents such as N,N-dimethylformamide or N,N-dimethylacetamide, its fluorinated analogue offers advantages in reactions that benefit from enhanced polarity and reduced nucleophilicity of the solvent medium.

In organic synthesis, the compound serves as an intermediate in the preparation of other fluorinated molecules. The electron-withdrawing trifluoromethyl group increases the stability of the amide bond, and the compound can undergo further transformations to yield derivatives of potential value in medicinal and agrochemical chemistry. Fluorinated amides such as this one have been used to design molecules with altered metabolic stability and bioavailability, properties that are highly desirable in drug discovery. Although 2,2,2-trifluoro-N,N-dimethylacetamide itself is not employed as a therapeutic agent, it contributes to the synthesis of fluorinated scaffolds that are tested for biological activity.

Another area of application lies in materials research, where fluorinated compounds are valued for their resistance to heat and chemical degradation. 2,2,2-Trifluoro-N,N-dimethylacetamide can be incorporated into synthetic routes that produce fluorine-containing polymers, coatings, and specialty chemicals. These materials often exhibit low surface energy, high resistance to solvents, and long-term durability, properties that have practical uses in high-performance industrial applications.

The discovery and application of 2,2,2-trifluoro-N,N-dimethylacetamide highlight the importance of introducing fluorine into simple organic molecules. Its structural features make it a valuable member of the family of trifluoromethylated amides, combining the solubility and stability of a tertiary amide with the strong electronic influence of the trifluoromethyl group. As part of the broader expansion of organofluorine chemistry, this compound has served as a tool for synthetic chemists and has contributed indirectly to developments in pharmaceuticals, agrochemicals, and advanced materials.

References

2025. Tailored Li-ion battery electrodes and electrolytes for extreme condition operations. Communications Chemistry, 8(1).
DOI: 10.1038/s42004-025-01564-5

2023. Regio- and enantioselective remote dioxygenation of internal alkenes. Nature Chemistry, 15(6).
DOI: 10.1038/s41557-023-01192-3

2023. A molecular sieve-containing protective separator to suppress the shuttle effect of redox mediators in lithium-oxygen batteries. Nano Research, 16(7).
DOI: 10.1007/s12274-023-5663-5