646-97-9 | 1,1,1-Trifluoro-2-(trifluoromethyl)pent-4-en-2-ol

CAS:646-97-9 | 1,1,1-Trifluoro-2-(trifluoromethyl)pent-4-en-2-ol ,Description

1,1,1-Trifluoro-2-(trifluoromethyl)pent-4-en-2-ol, commonly known as 1,1,1-TFM, is a fluorinated alcohol that is used in a variety of applications, ranging from pharmaceuticals to industrial solvents. It is a colorless liquid that is soluble in both water and organic solvents. It is considered to be a versatile molecule, due to its ability to act as a reactant, intermediate, or solvent.
 

Scientific Research Applications

Isomerisation Reactions

The compound undergoes isomerisation reactions in a basic medium, with studies showing the rearrangement of its structure facilitated by bases such as triethylamine (Tordeux et al., 2001). This process assists in the intramolecular hydrogen transfer to yield a more stable isomer.

Synthesis of Derivatives

1,1,1-Trifluoro-2-(trifluoromethyl)pent-4-en-2-ol is used in the synthesis of various derivatives, including Schiff's bases and heteroolefins. These derivatives are created through reactions with anilines and exhibit distinct chemical properties, as indicated by NMR spectroscopy (Haas et al., 1997).

Enantioselective Synthesis

The compound is instrumental in enantioselective synthesis processes. For example, it has been used in the highly enantioselective synthesis of trifluoroalkan-2-ols through ruthenium-catalyzed hydrogenation, demonstrating its utility in producing enantiomerically pure compounds (Kuroki et al., 2000).

Lipase-Mediated Kinetic Resolution

Lipase-mediated kinetic resolution of the compound's esters leads to high enantiomeric purity, further emphasizing its role in stereocontrolled chemical processes. This resolution is key for transforming the resolved alcohol into other derivatives like 1,1,1-trifluoro-2,3-epoxypropane (Shimizu et al., 1996).

Palladium-Catalyzed Cycloisomerization

The compound has been used in the synthesis of furans through palladium-catalyzed cycloisomerization. This method showcases its versatility in the formation of complex organic structures (Zhang et al., 2007).

Hydrogenation and Reductive Deamination

It's an intermediate in the synthesis of β-trifluoromethylated aldol products. Its hydrogenation and reductive deamination further demonstrate its utility in creating diverse chemical structures (Funabiki et al., 2010).

Formation of N-Trifluoromethylhydroxylamines

The compound engages in ene reactions to form N-alkenyl-N-trifluoromethylhydroxylamines, indicating its reactivity and potential in the synthesis of novel organic compounds (Barlow et al., 1980).

Synthesis of CF3-Containing Compounds

Its derivatives are crucial in the synthesis of CF3-pyrazoles and furan-3-ones, highlighting its role in the creation of fluorinated building blocks for diverse chemical applications (Bazhin et al., 2014).

Synthesis of Trifluoromethylpyrimidines

The compound aids in synthesizing trifluoromethylpyrimidines from acetylacetone and trifluoroacetonitrile, showcasing its utility in heterocyclic chemistry (Dorokhov et al., 1991).

Synthesis of N-Substituted Oxazinanes

It serves as a precursor in synthesizing N-substituted oxazinanes, further emphasizing its versatility in organic synthesis (Zanatta et al., 2005).

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