N,N-Dimethyl-1,1,2,2-tetrafluoroethylamine
[CAS# 1550-50-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: N,N-Dimethyl-1,1,2,2-tetrafluoroethylamine
• Synonyms: 1,1,2,2-Tetrafluoro-N,N-dimethylethanamine
• Molecular Formula: C₄H₇F₄N
• Molecular Weight: 145.10
• CAS Registry Number: 1550-50-1
• EC Number: 604-996-3
• SMILES: CN(C)C(C(F)F)(F)F

Properties

• Density: 1.24
• Boiling point: 77 ºC
• Flash point: 8 ºC

Safety Data

• Hazard Symbols: GHS05;GHS06 Danger
• Hazard Statements: H300-H310-H314-H330
• Precautionary Statements: P260-P262-P264-P270-P271-P280-P284-P301+P316-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P320-P321-P330-P361+P364-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	2	H300
Acute toxicity	Acute Tox.	1	H310
Skin corrosion	Skin Corr.	1A	H314
Acute toxicity	Acute Tox.	1	H330
Flammable liquids	Flam. Liq.	2	H225
Skin corrosion	Skin Corr.	1B	H314

• Transport Information: UN 2734

Discovory and Applicatios

N,N-Dimethyl-1,1,2,2-tetrafluoroethylamine is an organofluorine compound with the chemical formula C₅H₈F₄N. It is a derivative of ethylamine, where the ethyl group is substituted with four fluorine atoms, creating a highly fluorinated amine. The discovery and applications of N,N-dimethyl-1,1,2,2-tetrafluoroethylamine highlight its significance in various fields, particularly in organic synthesis and materials science.

The synthesis of N,N-dimethyl-1,1,2,2-tetrafluoroethylamine typically involves the fluorination of ethylamine. This process introduces fluorine atoms at the 1 and 2 positions of the ethyl group, while the nitrogen is also methylated to yield the dimethylated amine. The fluorination process is carried out using various fluorinating agents, which are carefully selected to achieve the desired level of fluorination without introducing unwanted by-products.

One of the primary applications of N,N-dimethyl-1,1,2,2-tetrafluoroethylamine is in the field of organic synthesis. The fluorinated amine is used as a reagent or intermediate in the preparation of other fluorinated compounds. The presence of fluorine atoms in the molecule imparts unique chemical properties, such as increased stability and altered reactivity, which are valuable in the synthesis of complex organic molecules.

In medicinal chemistry, N,N-dimethyl-1,1,2,2-tetrafluoroethylamine and its derivatives are explored for their potential therapeutic applications. The fluorine atoms contribute to the molecule's metabolic stability and biological activity. Fluorinated amines are often incorporated into pharmaceutical compounds to enhance their pharmacokinetic and pharmacodynamic properties. Research into the biological activity of fluorinated amines has shown that they can affect enzyme activity, receptor binding, and overall drug efficacy.

The compound is also utilized in materials science, particularly in the development of fluorinated polymers and materials. The fluorine atoms in N,N-dimethyl-1,1,2,2-tetrafluoroethylamine can be used to introduce fluorinated functional groups into polymers, which can enhance their properties such as chemical resistance, thermal stability, and surface wettability. These properties make fluorinated materials suitable for applications in coatings, adhesives, and other high-performance materials.

Additionally, N,N-dimethyl-1,1,2,2-tetrafluoroethylamine is employed in the electronics industry. The compound's unique fluorinated structure makes it useful in the development of electronic materials and components that require high thermal and chemical stability. It is used in the synthesis of fluorinated compounds that are integral to advanced electronic devices and systems.

In summary, N,N-dimethyl-1,1,2,2-tetrafluoroethylamine is a versatile fluorinated amine with significant applications in organic synthesis, medicinal chemistry, materials science, and electronics. Its unique chemical properties enable its use in various advanced technologies and products.

References

2010. Fluorine-containing β,β-disubstituted trimethylsilyl vinyl ethers: synthesis and reactions with N-(1,1,2,2-tetrafluoroethyl)dimethylamine. Russian Chemical Bulletin, 59, 3.
DOI: 10.1007/s11172-010-0134-z

2017. Recent Developments in the Deoxyfluorination of Alcohols and Phenols: New Reagents, Mechanistic Insights, and Applications. Synthesis, 49, 16.
DOI: 10.1055/s-0036-1590881

2020. Recent Advances in the Synthesis of Acyl Fluorides. Synthesis, 52, 20.
DOI: 10.1055/s-0040-1705951