431-40-3

Usage

Uses

Used in Organic Synthesis:
1,1,1-Trifluoroacetone oxime is used as a key intermediate in the synthesis of various organic compounds, facilitating the creation of a wide array of chemical products.
Used as a Reagent in Chemical Conversions:
In the field of organic chemistry, 1,1,1-trifluoroacetone oxime is utilized as a reagent for the conversion of carbonyl compounds to their corresponding oximes. This conversion is essential for the protective group strategy in the preparation of sensitive aldehyde and ketone compounds, enhancing their stability and reactivity in subsequent reactions.
Used in Pharmaceutical Industry:
1,1,1-Trifluoroacetone oxime is studied for its potential applications in the development of new pharmaceuticals. Its unique properties may contribute to the creation of innovative drug candidates, although further research is necessary to fully explore and understand its capabilities in this field.

InChI:InChI=1/C3H4F3NO/c1-2(7-8)3(4,5)6/h8H,1H3/b7-2+

Upstream product

• 421-50-1 1,1,1-trifluoro-2-propanone 

Downstream Products

• 421-49-8 2,2,2-Trifluoro-1-methylethanamine 
• 40618-85-7 C₁₀H₁₀F₃NO₃S 

Relevant academic research and scientific papers

Synthesis and spin-trapping properties of a trifluoromethyl analogue of DMPO: 5-methyl-5-trifluoromethyl-1-pyrroline N-Oxide (5-TFDMPO)

The 5-diethoxyphosphonyl-5-methyl-1-pyrroline N-oxide superoxide spin adduct (DEPMPO-OOH) is much more persistent (about 15 times) than the 5,5-dimethyl-1-pyrroline N-oxide superoxide spin adduct (DMPO-OOH). The diethoxyphosphonyl group is bulkier than the methyl group and its electron-withdrawing effect is much stronger. These two factors could play a role in explaining the different half-lifetimes of DMPO-OOH and DEPMPO-OOH. The trifluoromethyl and the diethoxyphosphonyl groups show similar electron-withdrawing effects but have different sizes. We have thus synthesized and studied 5-methyl-5-trifluoromethyl-1-pyrroline N-oxide (5-TFDMPO), a new trifluoromethyl analogue of DMPO, to compare its spin-trapping performance with those of DMPO and DEPMPO. 5-TFDMPO was prepared in a five-step sequence by means of the Zn/AcOH reductive cyclization of 5,5,5-trifluoro-4-methyl-4- nitropentanal, and the geometry of the molecule was estimated by using DFT calculations. The spin-trapping properties were investigated both in toluene and in aqueous buffer solutions for oxygen-, sulfur-, and carbon-centered radicals. All the spin adducts exhibit slightly different fluorine hyperfine coupling constants, thereby suggesting a hindered rotation of the trifluoromethyl group, which was confirmed by variable-temperature EPR studies and DFT calculations. In phosphate buffer at pH-7.4, the half-life of 5-TFDMPO-OOH is about three times shorter than for DEPMPO-OOH and five times longer than for DMPO-OOH. Our results suggest that the stabilization of the superoxide adducts comes from a delicate balance between steric, electronic, and hydrogen-bonding effects that involve the β group, the hydroperoxyl moiety, and the nitroxide. New pieces to the puzzle! A new fluorinated 5,5-dimethyl-1-pyrroline N-oxide (DMPO)-based spin trap (5-TFDMPO; see figure) was synthesized and studied by EPR/spin-trapping techniques. The properties of the new spin trap are reported for various radicals. The role of the trifluoromethyl group on the spin-trapping properties of the superoxide radical is discussed on the basis of a comparison with other spin traps.

Economical and practical strategies for synthesis of α-trifluoromethylated amines

A powerful approach to synthesize α-trifluoromethylated amines has been developed. The method is operationally simple, broad in substrate scope and amenable to scale-up using trifluoroacetic anhydride. Meanwhile, the strategy not only provided a versatile approach to synthesize α-trifluoromethylated amines but also provides a new method for exploring the new reactivity of trifluoroacetic anhydride.