130336-16-2 | 3',5'-DICHLORO-2,2,2-TRIFLUOROACETOPHENONE

CAS:130336-16-2 | 3',5'-DICHLORO-2,2,2-TRIFLUOROACETOPHENONE,Description

While the provided papers do not directly discuss 3',5'-Dichloro-2,2,2-trifluoroacetophenone, they offer insights into related compounds that can help infer some aspects of its chemistry. The first paper discusses 2,4,5-Trihydroxy-3-methylacetophenone, a compound with a weak aromatic system that exhibits different tautomeric forms under various conditions. The second paper examines 5-Chloro-3-nitro-2-hydroxyacetophenone, focusing on its conformational changes and phototransformations when isolated in an argon matrix and exposed to UV radiation. These studies suggest that substitutions on the acetophenone ring can significantly affect the molecule's reactivity and stability.

Synthesis Analysis

Molecular Structure Analysis

The molecular structure of 3',5'-Dichloro-2,2,2-trifluoroacetophenone would be expected to have a significant impact on its chemical properties. The presence of electron-withdrawing groups such as chloro and trifluoromethyl would likely enhance the electrophilic character of the carbonyl carbon, making it more susceptible to nucleophilic attack. The steric and electronic effects of these substituents could also influence the molecule's conformation and reactivity, as seen in the case of 5-Chloro-3-nitro-2-hydroxyacetophenone.

Chemical Reactions Analysis

The chemical reactivity of 3',5'-Dichloro-2,2,2-trifluoroacetophenone can be inferred from the behavior of related compounds. For instance, the presence of hydroxyl and acetyl groups in 2,4,5-Trihydroxy-3-methylacetophenone affects its aromaticity and reactivity towards oxidation and nitration. Similarly, the chloro and trifluoromethyl groups in 3',5'-Dichloro-2,2,2-trifluoroacetophenone would influence its reactivity, potentially making it more resistant to certain reactions due to the electron-withdrawing nature of these substituents.

Physical and Chemical Properties Analysis

The physical and chemical properties of 3',5'-Dichloro-2,2,2-trifluoroacetophenone, such as melting point, boiling point, solubility, and stability, would be affected by the dichloro and trifluoromethyl groups. These groups would likely increase the compound's density and boiling point compared to unsubstituted acetophenone. The electron-withdrawing effect could also affect the acidity of any hydrogen atoms adjacent to the carbonyl group, potentially leading to differences in solubility and reactivity in various solvents. The studies on related compounds suggest that such substitutions can lead to increased oxidative stability and altered reactivity.

Scientific Research Applications

Platinum-Catalyzed Enantioselective Hydrogenation

Platinum-catalyzed enantioselective hydrogenation of aryl-substituted trifluoroacetophenones, including 3',5'-Dichloro-2,2,2-trifluoroacetophenone, has been studied. Electron-withdrawing groups like CF3 increased the rate and enantioselectivity of these reactions, making it a significant process in heterogeneous catalyst systems (Arx, Mallát, & Baiker, 2001).

Synthesis of Fluorinated Monomers

A ‘3F’ fluorinated diamine monomer based on trifluoroacetophenone was synthesized for creating new polyimides. These polyimides show excellent thermal stability and solvent resistance, highlighting the utility of 3',5'-Dichloro-2,2,2-trifluoroacetophenone in polymer science (Brink et al., 1994).

Catalytic Precursors in Asymmetric Reduction

Ruthenium(II) complexes with specific ligands, including 3',5'-Dichloro-2,2,2-trifluoroacetophenone, have been used as catalytic precursors for the asymmetric reduction of trifluoroacetophenone to α-(trifluoromethyl)benzyl alcohol (Barbaro et al., 2003).

Environmentally Friendly Epoxidation

2,2,2-Trifluoroacetophenone serves as an efficient organocatalyst for the epoxidation of alkenes, offering an environmentally friendly and chemoselective method with high yields using H2O2 as the green oxidant. This highlights its potential in green chemistry applications (Limnios & Kokotos, 2014).

Gas Transport Properties in Polymers

New aromatic 3F polymers derived from 2,2,2-trifluoroacetophenone have shown attractive permeability coefficients for gases like CO2 and H2. These polymers are noted for their high glass transition temperatures and excellent thermal stability, making them suitable for industrial applications (Guzmán-Gutiérrez et al., 2008) .

Fluorescence Sensing of Carboxylate Anions

Oligothiophene-based o-(carboxamido)trifluoroacetophenones exhibit fluorescence enhancement upon binding with carboxylate anions. This finding is significant in the development of fluorescence-based sensors (Kim & Ahn, 2008).

Safety And Hazards

This compound is known to cause skin irritation and serious eye irritation. Precautionary measures include washing skin thoroughly after handling, wearing protective gloves/eye protection/face protection, and seeking medical advice if skin or eye irritation persists.

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