78950-29-5

Usage

Uses

Used in Organic Synthesis:
4-(Trifluoromethyl)phenyl acetate is used as a reagent for the formation of arylic and aliphatic compounds, due to its electron-withdrawing trifluoromethyl group which provides stability and resistance against reactions.
Used in Pharmaceutical Industry:
4-(Trifluoromethyl)phenyl acetate is used as a building block in the synthesis of various pharmaceutical compounds, contributing to the development of new drugs with improved properties.
Used in Agrochemical Industry:
4-(Trifluoromethyl)phenyl acetate is used in the production of agrochemicals, such as pesticides and herbicides, where its stability and resistance against reactions are beneficial for the performance of these products.
Safety Considerations:
4-(Trifluoromethyl)phenyl acetate is typically a clear colorless liquid and should be handled with care as it may cause irritation to the skin and eyes. Proper safety measures should be taken during its use and storage to minimize potential health risks.

InChI:InChI=1/C9H7F3O2/c1-6(13)14-8-4-2-7(3-5-8)9(10,11)12/h2-5H,1H3

Upstream product

• 75-97-8 3,3-dimethyl-butan-2-one 
• 402-45-9 4-hydroxybenzotrifluoride 
• 98-08-8 α,α,α-trifluorotoluene 
• 33035-41-5 2-(diacetoxyiodo)mesitylene 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 64-19-7 acetic acid 
• 455-13-0 4-Iodobenzotrifluoride 
• 6018-89-9 nickel(II) acetate tetrahydrate 
• 15761-39-4 N-tert-butoxycarbonyl-proline 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 33527-94-5 4-acetoxyiodobenzene 
• 75-36-5 acetyl chloride 

Downstream Products

• 721-63-1 (4-trifluoromethylphenyl)acetic acid ethyl ester 

Relevant academic research and scientific papers

Coupling of Alternating Current to Transition-Metal Catalysis: Examples of Nickel-Catalyzed Cross-Coupling

The coupling of transition-metal to photoredox catalytic cycles through single-electron transfer steps has become a powerful tool in the development of catalytic processes. In this work, we demonstrated that transition-metal catalysis can be coupled to al

Semi-heterogeneous Dual Nickel/Photocatalysis using Carbon Nitrides: Esterification of Carboxylic Acids with Aryl Halides

Cross-coupling reactions mediated by dual nickel/photocatalysis are synthetically attractive but rely mainly on expensive, non-recyclable noble-metal complexes as photocatalysts. Heterogeneous semiconductors, which are commonly used for artificial photosynthesis and wastewater treatment, are a sustainable alternative. Graphitic carbon nitrides, a class of metal-free polymers that can be easily prepared from bulk chemicals, are heterogeneous semiconductors with high potential for photocatalytic organic transformations. Here, we demonstrate that graphitic carbon nitrides in combination with nickel catalysis can induce selective C?O cross-couplings of carboxylic acids with aryl halides, yielding the respective aryl esters in excellent yield and selectivity. The heterogeneous organic photocatalyst exhibits a broad substrate scope, is able to harvest green light, and can be recycled multiple times. In situ FTIR was used to track the reaction progress to study this transformation at different irradiation wavelengths and reaction scales.

Donor-Acceptor Fluorophores for Energy-Transfer-Mediated Photocatalysis

Triplet-triplet energy transfer (EnT) is a fundamental activation pathway in photocatalysis. In this work, we report the mechanistic origins of the triplet excited state of carbazole-cyanobenzene donor-acceptor (D-A) fluorophores in EnT-based photocatalytic reactions and demonstrate the key factors that control the accessibility of the 3LE (locally excited triplet state) and 3CT (charge-transfer triplet state) via a combined photochemical and transient absorption spectroscopic study. We found that the energy order between 1CT (charge transfer singlet state) and 3LE dictates the accessibility of 3LE/3CT for EnT, which can be effectively engineered by varying solvent polarity and D-A character to depopulate 3LE and facilitate EnT from the chemically more tunable 3CT state for photosensitization. Following the above design principle, a new D-A fluorophore with strong D-A character and weak redox potential is identified, which exhibits high efficiency for Ni(II)-catalyzed cross-coupling of carboxylic acids and aryl halides with a wide substrate scope and high selectivity. Our results not only provide key fundamental insight on the EnT mechanism of D-A fluorophores but also establish its wide utility in EnT-mediated photocatalytic reactions.

Ligand-Promoted Palladium-Catalyzed C?H Acetoxylation of Simple Arenes

The palladium-catalyzed C?H oxidation of simple arenes is an attractive strategy to obtain phenols, which have many applications in the fine chemicals industry. Although some advances have been made in this research area, low reactivity and selectivity are, in general, observed. This report describes a new catalytic system for the efficient C?H acetoxylation of simple arenes based on Pd(OAc)2 and a pyridinecarboxylic acid ligand.

TCDA: Practical Synthesis and Application in the Trifluoromethylation of Arenes and Heteroarenes

A practical synthesis of the reagent trimethylsilyl chlorodifluoroacetate (TCDA) is reported on 50 g scale. The trifluoromethylation with TCDA was optimized, and the reaction shows very broad scope with respect to electron-deficient, -neutral, -rich aryl/heteroaryl iodides, as well as excellent functional group tolerability, such as ester, amide, aldehyde, hydroxyl, and carboxylic acid. The reagent was also applied to the late-stage trifluoromethylation of three medicinally relevant compounds. Additionally, the building block trifluoromethylpyridine and one drug related molecule Boc-Fluoxetin were synthesized in 10 g scale by this method, demonstrating its practical applications in process chemistry.

Magnetically separable γ-Fe2O3 nanoparticles: An efficient catalyst for acylation of alcohols, phenols, and amines using sonication energy under solvent free condition

This paper reports a facile synthesis of magnetically separable iron oxide (γ-Fe2O3) nanoparticles using thermolysis method. The structural and morphological study of the synthesized γ-Fe2O3 nanoparticles was carried out using X-ray diffraction (XRD), field emission gun-scanning electron microscopy (FEG-SEM), energy dispersive X-ray spectrum (EDS), transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), and X-ray photoelectron spectroscopy (XPS) techniques. The electron microscopy reveals that the γ-Fe2O3 nanoparticles have spherical morphology with a particle size in the range of 40-100 nm. The XPS study confirmed the Fe is in +3 oxidation state. The synthesized γ-Fe2O3 nanoparticles have been used as an efficient heterogeneous catalyst for the organic transformation between phenols, alcohols, and amines with acetic anhydride under sonication using mild reaction conditions. Various electrons withdrawing and electrons donating substrates show an excellent yield of desired products with the advantage of magnetic separation and reusability of γ-Fe2O3 nanocatalyst.

New Reagent for Highly Efficient Synthesis of Trifluoromethyl-Substituted Arenes and Heteroarenes

A new reagent trimethylsilyl chlorodifluoroacetate (TCDA) is reported for the introduction of a -CF3 group to arenes and heteroarenes. Compared with current known reagents, TCDA shows very broad scope with respect to electron-deficient, -neutral, and -rich aryl/heteroaryl iodides as well as excellent functional group tolerance, including ester, amide, aldehyde, hydroxyl, and carboxylic acid. (Chemical Equation Presented).

A universal procedure for the [18F]trifluoromethylation of aryl iodides and aryl boronic acids with highly improved specific activity

Herein we describe a valuable method for the introduction of the [18F]CF3 group into arenes with highly improved specific activity by the reaction of [18F]trifluoromethane with aryl iodides or aryl boronic acids. This [su

Steric control of site selectivity in the Pd-catalyzed C-H acetoxylation of simple arenes

This report describes the use of an oxidant and a ligand to control site selectivity in the Pd(OAc)2-catalyzed C-H acetoxylation of simple arenes. The use of MesI(OAc)2 as the terminal oxidant in combination with acridine as the ligand results in primarily sterically controlled selectivity. In contrast, with Pd(OAc)2 as the catalyst and PhI(OAc)2 as the oxidant, electronic effects dominate the selectivity of arene C-H acetoxylation.

Remarkably high reactivity of Pd(OAc)2/pyridine catalysts: Nondirected C-H oxygenation of arenes

Less is more: The rational optimization and general applicability of the catalytic system Pd(OAc)2/pyridine is described (see scheme). The catalyst shows excellent reactivity in the C-H oxygenation of simple aromatic substrates. The Pd/pyridine ratio is critical as the use of one equivalent of pyridine per Pd center leads to dramatic enhancements in both reactivity and site selectivity in comparison to Pd(OAc)2 alone.