330-12-1

Usage

Uses

Used in Pharmaceutical Industry:
4-(Trifluoromethoxy)benzoic acid is used as a key intermediate for the synthesis of various biologically active compounds, primarily for its role in the development of antifungal and antimalarial agents. Its chemical structure allows for the creation of drugs that can effectively combat these diseases by targeting specific pathways in the pathogens.
Used in Chemical Industry:
In the chemical industry, 4-(Trifluoromethoxy)benzoic acid is utilized as a building block for the production of other complex organic molecules. Its trifluoromethoxy group provides unique reactivity and properties that can be exploited in the synthesis of a wide range of compounds, making it a versatile component in the development of new materials and chemicals.

InChI:InChI=1/C8H5F3O3/c9-8(10,11)14-6-3-1-5(2-4-6)7(12)13/h1-4H,(H,12,13)

Upstream product

• 927-84-4 bis(trifluoromethyl)peroxide 
• 65-85-0 benzoic acid 
• 1736-08-9 4-ethenylphenyl trifluoromethyl ether 
• 124-38-9 carbon dioxide 
• 169222-42-8 (4-(trifluoromethoxy)-phenyl)magnesium bromide 
• 659-28-9 p-trifluoromethoxybenzaldehyde 
• 150162-39-3 N-hydroxy-1-[4-(trifluoromethoxy)phenyl]methaneimine 
• 1736-74-9 4-trifluoromethoxybenzyl alcohol 
• 50824-05-0 4-trifluoromethoxybenzyl bromide 
• 332-25-2 4-(trifluoromethoxy)benzonitrile 
• 407-14-7 1-bromo-4-(trifluoromethoxy)benzene 

Downstream Products

• 27914-35-8 C₂₂H₂₂F₆N₂O₄ 
• 27914-45-0 C₂₃H₂₂F₆N₂O₅ 
• 28510-16-9 C₂₃H₂₀F₆N₂O₄ 
• 27890-89-7 C₃₁H₂₈F₉N₃O₆ 
• 27890-80-8 C₂₁H₂₀F₆N₂O₄ 
• 27914-62-1 C₂₀H₁₈F₆N₂O₄Se₂ 
• 27914-36-9 C₂₃H₂₄F₆N₂O₄ 
• 27914-37-0 C₂₄H₂₆F₆N₂O₄ 
• 27914-42-7 C₂₂H₂₂F₆N₂O₅ 
• 27914-41-6 C₂₃H₂₅F₆N₃O₄ 
• 27890-79-5 C₂₅H₂₈F₆N₂O₄ 
• 27890-82-0 C₂₆H₃₀F₆N₂O₄ 
• 27890-96-6 C₂₇H₃₂F₆N₂O₄ 
• 27890-94-4 C₂₈H₃₄F₆N₂O₄ 

Relevant academic research and scientific papers

Milled Dry Ice as a C1 Source for the Carboxylation of Aryl Halides

The use of carbon dioxide as a C1 chemical feedstock remains an active field of research. Here we showcase the use of milled dry ice as a method to promote the availability of CO 2in a reaction solution, permitting practical synthesis of arylcarboxylic acids. Notably, the use of milled dry ice produces marked increases in yields relative to those obtained with gaseous CO 2, as previously reported in the literature.

1,2-Dibutoxyethane-Promoted Oxidative Cleavage of Olefins into Carboxylic Acids Using O2 under Clean Conditions

Herein, we report the first example of an effective and green approach for the oxidative cleavage of olefins to carboxylic acids using a 1,2-dibutoxyethane/O2 system under clean conditions. This novel oxidation system also has excellent functional-group tolerance and is applicable for large-scale synthesis. The target products were prepared in good to excellent yields by a one-pot sequential transformation without an external initiator, catalyst, and additive.

Radical C?H Trifluoromethoxylation of (Hetero)arenes with Bis(trifluoromethyl)peroxide

Trifluoromethoxylated (hetero)arenes are of great interest for several disciplines, especially in agro- and medicinal chemistry. Radical C?H trifluoromethoxylation of (hetero)arenes represents an attractive approach to prepare such compounds, but the high cost and low atom economy of existing .OCF3 radical sources make them unsuitable for the large-scale synthesis of trifluoromethoxylated building blocks. Herein, we introduce bis(trifluoromethyl)peroxide (BTMP, CF3OOCF3) as a practical and efficient trifluoromethoxylating reagent that is easily accessible from inexpensive bulk chemicals. Using either visible light photoredox or TEMPO catalysis, trifluoromethoxylated arenes could be prepared in good yields under mild conditions directly from unactivated aromatics. Moreover, TEMPO catalysis allowed for the one-step synthesis of valuable pyridine derivatives, which have been previously prepared via multi-step approaches.

An Anionic, Chelating C(sp3)/NHC ligand from the Combination of an N-heterobicyclic Carbene and Barbituric Heterocycle

The coordination chemistry of the anionic NHC1-based on an imidazo[1,5-a]pyridin-3-ylidene (IPy) platform substituted at the C5 position by an anionic barbituric heterocycle was studied with d6(Ru(II), Mn(I)) and d8(Pd(II), Rh(I), Ir(I), Au(III)) transition-metal centers. While the anionic barbituric heterocycle is planar in the zwitterionic NHC precursor 1·H, NMR spectroscopic analyses supplemented by X-ray diffraction studies evidenced the chelating behavior of ligand 1-through the carbenic and the malonic carbon atoms in all of the complexes, resulting from a deformation of the lateral barbituric heterocycle. The complexes were obtained by reaction of the free carbene with the appropriate metal precursor, except for the Au(III) complex 10, which was obtained by oxidation of the antecedent gold(I) complex [AuCl(1)]?with PhICl2as an external oxidant. During the course of the process, the kinetic gold(I) intermediate 9 resulting from the oxidation of the malonic carbon of the barbituric moiety was isolated upon crystallization from the reaction mixture. The νCOstretching frequencies recorded for complex [Rh(1)(CO)2] (5) demonstrated the strong donating character of the malonate-C(sp3)/NHC ligand 1-. The ruthenium complex [Ru(1)Cl(p-cymene)] (11) was implemented as a precatalyst in the dehydrogenative synthesis of carboxylic acid derivatives from primary alcohols and exhibited high activities at low catalyst loadings (25-250 ppm) and a large tolerance toward functional groups.

Photocatalytic trifluoromethoxylation of arenes and heteroarenes in continuous-flow

The first example of photocatalytic trifluoromethoxylation of arenes and heteroarenes under continuous-flow conditions is described. Application of continuous-flow microreactor technology allowed to reduce the residence time up to 16 times in comparison t

CO2 (De)Activation in Carboxylation Reactions: A Case Study Using Grignard Reagents and Nucleophilic Bases

Carbon dioxide (CO2) is an intrinsically stable molecule. However, its reactivity toward nucleophilic bases has constituted an appealing characteristic for applications such as CO2 capture and functionalization. To shed light on the role of nucleophilic bases in CO2 functionalization, we performed some mechanistic studies using nitrogen-containing bases as an additive-in catalytic amounts-for carboxylation reactions of Grignard reagents. Our kinetic analysis and in situ infrared spectroscopy revealed the role of nucleophilic bases, particularly that of DBU (1,8-diazabicycloundec-7-ene), in CO2 (de)activation for carboxylation reactions.

Carboxylation of Aryl Triflates with CO2 Merging Palladium and Visible-Light-Photoredox Catalysts

We report herein a visible-light-promoted, highly practical carboxylation of readily accessible aryl triflates at ambient temperature and a balloon pressure of CO2 by the combined use of palladium and photoredox Ir(III) catalysts. Strikingly, the stoichiometric metallic reductant is replaced by a nonmetallic amine reductant providing an environmentally benign carboxylation process. In addition, one-pot synthesis of a carboxylic acid directly from phenol and modification of estrone and concise synthesis of pharmaceutical drugs adapalene and bexarotene have been accomplished via late-stage carboxylation reaction. Furthermore, a parallel decarboxylation-carboxylation reaction has been demonstrated in an H-type closed vessel that is an interesting concept for the strategic sector. Spectroscopic and spectroelectrochemical studies indicated electron transfer from the Ir(III)/DIPEA combination to generate aryl carboxylate and Pd(0) for catalytic turnover.

DIFLUOROMETHOXYLATION AND TRIFLUOROMETHOXYLATION COMPOSITIONS AND METHODS FOR SYNTHESIZING SAME

The present invention provides a compound having the structure (I), a processing of making the compound; and a process of using the compound as a reagent for the difluoromethoxylation and trifluoromethoxylation of arenes or heteroarenes.

Highly active bidentate N-heterocyclic carbene/ruthenium complexes performing dehydrogenative coupling of alcohols and hydroxides in open air

Eight bidentate NHC/Ru complexes, namely [Ru]-1-[Ru]-8, were designed and prepared. In particular, [Ru]-2 displayed extraordinary performance even in open air for the dehydrogenative coupling of alcohols and hydroxides. Notably, an unprecedentedly low catalyst loading of 250 ppm and the highest TON of 32 800 and TOF of 3200 until now were obtained.

Continuous Platform to Generate Nitroalkanes On-Demand (in Situ) Using Peracetic Acid-Mediated Oxidation in a PFA Pipes-in-Series Reactor

The synthetic utility of the aza-Henry reaction can be diminished on scale by potential hazards associated with the use of peracid to prepare nitroalkane substrates and the nitroalkanes themselves. In response, a continuous and scalable chemistry platform to prepare aliphatic nitroalkanes on-demand using the oxidation of oximes with peracetic acid and direct reaction of the nitroalkane intermediate in an aza-Henry reaction is reported. A uniquely designed pipes-in-series plug-flow tube reactor addresses a range of process challenges, including stability and safe handling of peroxides and nitroalkanes. The subsequent continuous extraction generates a solution of purified nitroalkane, which can be directly used in the following enantioselective aza-Henry chemistry to furnish valuable chiral diamine precursors with high selectivity, thus completely avoiding isolation of the potentially unsafe low-molecular-weight nitroalkane intermediate. A continuous campaign (16 h) established that these conditions were effective in processing 100 g of the oxime and furnishing 1.4 L of nitroalkane solution.