421-49-8 | 1,1,1-Trifluoropropan-2-amine

CAS:421-49-8 | 1,1,1-Trifluoropropan-2-amine ,Description

1,1,1-Trifluoropropan-2-amine, also known as N-Trifluoromethylpropan-2-amine, is an organic compound with the chemical formula C3H7F3N. It is a colorless, volatile liquid with a strong, pungent odor. It is used in a variety of industrial, pharmaceutical, and agricultural applications, as well as in laboratory experiments. This compound is of particular interest due to its unique properties and its potential for use in a variety of applications.
 

Scientific Research Applications

Catalyst-Free Trifluoroethylation

1,1,1-Trifluoropropan-2-amine has been applied in catalyst-free trifluoroethylation reactions of amines. This approach is significant as it facilitates the functionalization of amines with a trifluoromethyl group, enabling the modification of biologically active compounds without requiring sensitive reagents or harsh conditions. The process is notable for its functional group tolerance, convenience, and use of trifluoroacetic acid as a fluorine source (Andrews et al., 2017).

Stereoselective Synthesis and Reactivity

Researchers have developed a stereoselective synthesis method for enantiomerically enriched 1,1,1-trifluoro-2-propanamine, highlighting its potential in stereoselective organic synthesis. This method includes a reduction step that yields amine derivatives with high diastereomeric excess. The synthesis route also explores the reactivity of the trifluoropropan-2-ammonium triflate enantiomers, particularly in reactions with epoxides (Packer et al., 2017).

Heterocyclization Reactions

1,1,1-Trifluoropropan-2-amine is involved in the heterocyclization reactions for synthesizing fluorinated compounds. It's part of the synthesis of 1-substituted 4-amino-2-(trifluoromethyl)-1H-pyrroles, highlighting its role in introducing trifluoromethyl groups into heterocyclic compounds. This method is advantageous due to its simplicity, mild reaction conditions, and high yields, making it an environmentally friendly option (Aquino et al., 2015).

Encapsulation and Sensing Applications

The compound plays a role in the encapsulation of halides, serving as a potential receptor in pseudo-C3-symmetric cavities. This application is significant for sensing or sequestering halides, with implications in environmental monitoring and analytical chemistry (Lakshminarayanan et al., 2007).

Synthesis of Perfluoroalkylated Compounds

The compound is crucial in the synthesis of perfluoroalkylated amines and N-heterocycles. It contributes to the formation of perfluoroalkylated compound libraries, which are valuable for drug development, agrochemicals, and chemical-biology research. The use of perfluoro acid anhydrides in this process demonstrates the compound's versatility in organic synthesis (Kawamura et al., 2017).

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