447-61-0

Usage

Uses

Used in Pharmaceutical Industry:
2-(Trifluoromethyl)benzaldehyde is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its application is primarily due to its reactivity and the unique properties imparted by the trifluoromethyl group, which can enhance the biological activity and pharmacokinetic profile of the resulting drugs.
Used in Chemical Synthesis:
2-(Trifluoromethyl)benzaldehyde is used as a reagent in the preparation of complex organic molecules through reactions like the Wittig-Horner reaction. It serves as an electrophilic component, enabling the formation of new carbon-carbon double bonds and contributing to the synthesis of a wide array of chemical products.
Used in Material Science:
2-(Trifluoromethyl)benzaldehyde is also utilized in the development of novel materials with specific properties, such as improved stability or reactivity, due to the presence of the trifluoromethyl group. This makes it valuable in the creation of advanced materials for various applications, including electronics, coatings, and adhesives.

Synthesis Reference(s)

Tetrahedron, 49, p. 2151, 1993 DOI: 10.1016/S0040-4020(01)80359-8

InChI:InChI=1/C8H5F3O/c9-8(10,11)7-4-2-1-3-6(7)5-12/h1-5H

Upstream product

• 312-95-8 1-difluoromethyl-2-trifluoromethyl-benzene 
• 3048-01-9 o-trifluoromethylbenzylamine 
• 71859-75-1 hydroxyhydroperoxy(2-trifluorophenyl)methane 
• 346-06-5 (2-(trifluoromethyl)phenyl)methanol 
• 75-61-6 dibromodifluoromethane 
• 89-98-5 2-chloro-benzaldehyde 
• 111011-80-4 2-acetonyl-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinane 
• 152401-80-4 2-(dimorpholinomethyl)-1-(trifluoromethyl)benzene 
• 124215-21-0 (3aR,6S,8aR)-3-Phenyl-6-(2-trifluoromethyl-phenyl)-3a,4,8,8a-tetrahydro-[1,3]dioxepino[5,6-d]isoxazole 
• 124215-21-0 (3aS,6S,8aS)-3-Phenyl-6-(2-trifluoromethyl-phenyl)-3a,4,8,8a-tetrahydro-[1,3]dioxepino[5,6-d]isoxazole 
• 138955-48-3 1-(2-(trifluoromethyl)phenyl)-2-methoxyethene 
• 67-64-1 acetone 
• 93-61-8 N-methyl-N-phenylformamide 
• 3796-19-8 2-trifluoromethylphenylmagnesium chloride 

Downstream Products

• 312-94-7 2-trifluoromethylbenzoyl chloride 
• 781-89-5 2-Nitro-1-<2-trifluormethyl-phenyl>-propen-(1) 
• 152401-80-4 2-(dimorpholinomethyl)-1-(trifluoromethyl)benzene 
• 344-96-7 2-trifluoromethyl-benzoic acid methyl ester 
• 139979-25-2 2,4-diamino--6-<2-(2-trifluoromethylphenyl)ethenyl>-1,3,5-triazine 
• 137481-69-7 1,4-Dihydro-2,6-dimethyl-3,5-dinitro-4-<2-(trifluormethyl)phenyl>-pyridin 
• 137481-61-9 (R,S)-(E)-<2-(Trifluormethyl)benzyliden>2-(trifluormethyl)-α-(nitromethyl)-benzylamin 
• 127034-12-2 (E)-3-(2-trifluoromethylphenyl)-1-(3,4,5-trimethoxyphenyl)-3-phenylprop-2-en-1-one 
• 82128-99-2 2-(2-trifluoromethylphenyl)-2-trimethylsiloxyethanenitrile 
• 75530-27-7 3-Oxo-2-[1-(2-trifluoromethyl-phenyl)-meth-(E)-ylidene]-butyric acid 2-ethoxy-ethyl ester 
• 123760-65-6 (S)-3-Phenyl-2-(2-trifluoromethyl-benzylamino)-propionic acid 
• 81152-86-5 5-(2-Trifluoromethyl-phenyl)-1,3,4,5-tetrahydro-indeno[1,2-b]pyridin-2-one 
• 16204-36-7 3,3,6,6-tetraphenyl-1,2,4,5-tetroxane 
• 130012-05-4 3,3-Diphenyl-5-(2-trifluoromethyl-phenyl)-[1,2,4]trioxolane 

Relevant academic research and scientific papers

Efficient and selective oxidation of benzylic alcohol by O2 into corresponding aldehydes on a TiO2 photocatalyst under visible light irradiation: Effect of phenyl-ring substitution on the photocatalytic activity

The highly efficient and selective photocatalytic oxidation of benzyl alcohol and its derivatives substituted with-OCH3,-CH 3,-C(CH3)3,-Cl,-CF3 and-NO 2 into corresponding aldehydes has been successfully carried out on TiO2 in the presence of O2 under visible light irradiation. The photocatalytic activity for the formation of the aldehyde was evaluated by a pseudo-first-order reaction, and it was found that the activity is enhanced by phenyl-ring substitution with the electron-releasing groups (-OCH3,-CH3,-C(CH3)3) and the electron-withdrawing groups (-Cl,-CF3 and-NO2). The effects of the substituents and their orientation on the photocatalytic performance of selective oxidation reaction are discussed here. It was shown that the photocatalytic activities are influenced not only by the oxidative potentials of the reactants but also by the stability of the resonant structures of the benzylic alcohol radicals formed by oxidation with a hole, leading to further reactions to form corresponding aldehydes.

Synthesis of seven-membered ring containing difluoromethylene unit by Sc(OTf)3-catalyzed activation of single C-F bond in CF3 group

A Sc(OTf)3-catalyzed activation of a single C-F bond in a CF3 group is described. This reaction has two interesting features: (1) the synthesis of difluoromethylene compounds through Lewis acid-catalyzed activation of a single C-F bond in a CF3 group, and (2) the selective formation of a seven-membered ring over a five-membered ring.

An isocyanide ligand for the rapid quenching and efficient removal of copper residues after Cu/TEMPO-catalyzed aerobic alcohol oxidation and atom transfer radical polymerization

Transition metal catalysts play a prominent role in modern organic and polymer chemistry, enabling many transformations of academic and industrial significance. However, the use of organometallic catalysts often requires the removal of their residues from reaction products, which is particularly important in the pharmaceutical industry. Therefore, the development of efficient and economical methods for the removal of metal contamination is of critical importance. Herein, we demonstrate that commercially available 1,4-bis(3-isocyanopropyl)piperazine can be used as a highly efficient quenching agent (QA) and copper scavenger in Cu/TEMPO alcohol aerobic oxidation (Stahl oxidation) and atom transfer radical polymerization (ATRP). The addition ofQAimmediately terminates Cu-mediated reactions under various conditions, forming a copper complex that can be easily separated from both small molecules and macromolecules. The purification protocol for aldehydes is based on the addition of a small amount of silica gel followed byQAand filtration. The use ofQA?SiO2synthesizedin situresults in products with Cu content usually below 5 ppm. Purification of polymers involves only the addition ofQAin THF followed by filtration, leading to polymers with very low Cu content, even after ATRP with high catalyst loading. Furthermore, the addition ofQAcompletely prevents oxidative alkyne-alkyne (Glaser) coupling. Although isocyanideQAshows moderate toxicity, it can be easily converted into a non-toxic compound by acid hydrolysis.

Cerium(IV) Carboxylate Photocatalyst for Catalytic Radical Formation from Carboxylic Acids: Decarboxylative Oxygenation of Aliphatic Carboxylic Acids and Lactonization of Aromatic Carboxylic Acids

We found that in situ generated cerium(IV) carboxylate generated by mixing the precursor Ce(OtBu)4 with the corresponding carboxylic acids served as efficient photocatalysts for the direct formation of carboxyl radicals from carboxylic acids under blue light-emitting diodes (blue LEDs) irradiation and air, resulting in catalytic decarboxylative oxygenation of aliphatic carboxylic acids to give C-O bond-forming products such as aldehydes and ketones. Control experiments revealed that hexanuclear Ce(IV) carboxylate clusters initially formed in the reaction mixture and the ligand-to-metal charge transfer nature of the Ce(IV) carboxylate clusters was responsible for the high catalytic performance to transform the carboxylate ligands to the carboxyl radical. In addition, the Ce(IV) carboxylate cluster catalyzed direct lactonization of 2-isopropylbenzoic acid to produce the corresponding peroxy lactone and ?3-lactone via intramolecular 1,5-hydrogen atom transfer (1,5-HAT).

AN IMPROVED PROCESS FOR PREPARATION OF TRIFLUOROMETHYLBENZALDEHYDES AND INTERMEDIATES THEREOF

The present invention provides an in-situ process for preparation of a compound of formula 1 and intermediate thereof, These compounds are useful chemical intermediates for the production of pesticides and pharmaceutical products.

Selective Functionalization of Styrenes with Oxygen Using Different Electrode Materials: Olefin Cleavage and Synthesis of Tetrahydrofuran Derivatives

Electrode materials can have a significant impact on the course of an electrolysis reaction. Of particular interest is that different electrodes can generate different products from the same substrate. The electrode-material-selective transformations of styrene derivatives with molecular oxygen are reported. Platinum electrodes afford carbonyl products via cleavage of olefins, whereas tetrahydrofuran formation is achieved with carbon electrodes. A variety of different styrenes are available for both reactions. Electrolysis allows straightforward and mild chemical conversions that are metal- and oxidant-free. Electrochemical measurements illuminate the different effects of platinum and carbon electrodes on styrenes. The key to the differing reactions is probably that the oxidation potentials of the substrates are lower (higher HOMO energy) on carbon electrodes than on platinum electrodes. The adsorption of the substrates on carbon electrodes can also promote tetrahydrofuran formation.

Oxidation of Alcohols to Carbonyl Compounds Catalyzed by Oxo-Bridged Dinuclear Cerium Complexes with Pentadentate Schiff-Base Ligands under a Dioxygen Atmosphere

Ionic mononuclear and neutral dinuclear complexes of cerium(III) 3-L1-3-L9 bearing a series of dianionic pentadentate Schiff-base ligands were synthesized, characterized, and used as catalysts for N-oxyl radical-free aerobic alcohol oxidation. Reactions of Ce(NO3)3·6H2O with o-tert-butyl-substituted sterically hindered ligands NH(CH2CH2-Rfnet=CHC6H2-3-(tBu)-5-R2-2-OH)2 (for L1H2, R2 = tBu; for L2H2, R2 = OMe; and for L3H2, R2 = H) in the presence of triethylamine afforded the corresponding anionic cerium complexes [HNEt3][Ce(L1-3)(NO3)2] (3-L1-3-L3), whereas complexation with sterically less hindered ligands, such as NH(CH2CH2N=CHC6H2-3-R1-5-R2-2-OH)2 (for L4H2, R1 = OMe and R2 = H; for L5H2, R1 = H and R2 = tBu; for L6H2, R1 = H and R2 = OMe; for L7H2, R1 = H and R2 = H; for L8H2, R1 = H and R2 = NO2; and for L9H2, R1 = tBu and R2 = NO2), afforded neutral dinuclear complexes [Ce(L4-9)(NO3)]2 (3-L4-3-L9). Among these newly prepared complexes, complex 3-L1 was selected as the best catalyst for oxidizing primary and secondary alcohols under a dioxygen atmosphere without any N-oxyl radicals such as TEMPO to produce the corresponding carbonyl compounds, where the oxo-bridged dinuclear complex worked as a catalyst while maintaining its dinuclear skeleton during the catalytic cycle. In addition, an intramolecular redox process between the two cerium centers through the bridging oxygen atom played a key role in forming the ligand phenoxide radical-mediated TEMPO-free alcohol oxidation reaction.

Chemoselective Reduction of Sterically Demanding N,N-Diisopropylamides to Aldehydes

A sequential one-pot process for chemoselectively reducing sterically demanding N,N-diisopropylamides to aldehydes has been developed. In this reaction, amides are activated with EtOTf to form imidates, which are reduced with LiAlH(OR)3 [R = t-Bu, Et] to give aldehydes by hydrolysis of the resulting hemiaminals. The non-nucleophilic base 2,6-DTBMP remarkably improves reaction efficiency. The combination of EtOTf/2,6-DTBMP and LiAlH(O-t-Bu)3 was found to be optimal for reducing alkyl, alkenyl, alkynyl, and 2-monosubstituted aryl N,N-diisopropylamides. In contrast, EtOTf and LiAlH(OEt)3 in the absence of base were found to be optimal for reducing extremely sterically demanding 2,6-disubstituted N,N-diisopropylbenzamides. The reaction tolerates various reducible functional groups, including aldehyde and ketone. 1H NMR studies confirmed the formation of imidates stable in water. The synthetic usefulness of this methodology was demonstrated with N,N-diisopropylamide-directed ortho-metalation and C-H bond activation.

Cerium peroxo complex (by machine translation)

[A] is soluble in organic solvents, alcohol oxidation catalyst cerium peroxo complex can be used. Cerium peroxo complex [a], cerium, N, N ' - bis ([sarichiriden[sarichiriden]) diethylenetriamine backbone with the ligand. N, N ' - bis ([sarichiriden[sarichiriden]) diethylenetriamine backbone, substituted alkyl groups with aromatic substitutions at position 2 and 4. The, the ligands of the peroxo groups, two cerium atoms are linked 2. [Drawing] no (by machine translation)

Metal- and O2-Free Oxidative C-C Bond Cleavage of Aromatic Aldehydes

An oxidative C-C cleavage of aldehydes requiring neither metals nor O2 was discovered. Homobenzylic aldehydes and α-substituted homobenzylic aldehydes were cleaved to benzylic aldehydes and ketones, respectively, using nitrosobenzene as an oxidant. This reaction is chemoselective for aromatic aldehydes, as an aliphatic aldehyde was unreactive under these conditions, and other reactive functionality such as ketones and free alcohols are tolerated. A mechanism accounting for the fate of the lost carbon is proposed.