1736-56-7

Usage

Uses

Used in Pharmaceutical Industry:
4-(TRIFLUOROMETHYL)PHENYLGLYOXAL HYDRATE is used as a key intermediate in the synthesis of pharmaceuticals for its ability to readily react with various functional groups, facilitating the creation of diverse medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 4-(TRIFLUOROMETHYL)PHENYLGLYOXAL HYDRATE is utilized as a building block in the development of new agrochemicals, such as pesticides and herbicides, due to its high reactivity and capacity to form stable and effective molecules.
Used in Organic Synthesis:
4-(TRIFLUOROMETHYL)PHENYLGLYOXAL HYDRATE is employed as a reactive intermediate in organic synthesis for the formation of complex organic molecules, taking advantage of its propensity to engage in various chemical reactions.
Used in Research and Development:
4-(TRIFLUOROMETHYL)PHENYLGLYOXAL HYDRATE is also used in research and development settings to explore new chemical reactions and investigate its potential applications in creating novel molecules for different industries.

InChI:InChI=1/C9H5F3O2.H2O/c10-9(11,12)7-3-1-6(2-4-7)8(14)5-13;/h1-5H;1H2

Upstream product

• 709-63-7 1-(4-trifluoromethylphenyl)ethanone 
• 383-53-9 2-bromo-1-[4-(trifluoromethyl)phenyl]ethanone 
• 98-08-8 α,α,α-trifluorotoluene 

Downstream Products

• 118693-60-0 (S)-2-Amino-4-{(R)-1-(carboxymethyl-carbamoyl)-2-[1-hydroxy-2-oxo-2-(4-trifluoromethyl-phenyl)-ethylsulfanyl]-ethylcarbamoyl}-butyric acid 
• 2194-45-8 1-Trifluormethyl-4--benzol 
• 1029033-96-2 C₁₅H₂₃F₃N₄ 
• 1148028-86-7 (9H-pyrido[3,4-b]indol-1-yl)(4-(trifluoromethyl)phenyl)methanone 
• 1148028-95-8 (6-methyl-9H-pyrido[3,4-b]indol-1-yl)(4-(trifluoromethyl)phenyl)methanone 
• 1148028-91-4 (6-methoxy-9H-pyrido[3,4-b]indol-1-yl)(4-(trifluoromethyl)phenyl)methanone 

Relevant academic research and scientific papers

A novel class for carbonic anhydrases inhibitors and evaluation of their non-zinc binding

In this study, 23 different imidazole derivatives were synthesized, and the inhibitory properties of these derivatives against carbonic anhydrase I and II isoenzymes were investigated for the first time. The inhibition concentrations of the imidazole derivatives were found to be in the range of 2.89–115.5 nM. Docking studies examined the binding properties of the imidazole derivatives, and the structure–activity relationship is discussed. Theoretical calculations showed that the binding mode of the imidazole ring was non-zinc binding.

Asymmetric Conjugate Addition of α-Cyanoketones to Benzoyl Acrylonitrile Derivatives Using a Diaminomethylenemalononitrile Organocatalyst

A diaminomethylenemalononitrile (DMM) organocatalyst was used to efficiently promote asymmetric conjugate addition of various α-cyanoketones to benzoyl acrylonitrile derivatives. The corresponding 1,5-dicarbonyl compounds containing vicinal tertiary and quaternary stereogenic centers are versatile synthetic intermediates and were obtained in good yields and with excellent enantioselectivities (up to 96% ee). The present study describes the first successful examples of asymmetric conjugate addition reactions of α-cyanoketones with benzoyl acrylonitriles. In addition, the DMM organocatalyst can be recovered and reused up to five times without significant loss of either catalytic activity or enantioselectivity.

Stereocontrolled Synthesis of 1,4-Dicarbonyl Compounds by Photochemical Organocatalytic Acyl Radical Addition to Enals

We report a visible-light-mediated organocatalytic strategy for the enantioselective acyl radical conjugate addition to enals, leading to valuable 1,4-dicarbonyl compounds. The process capitalizes upon the excited-state reactivity of 4-acyl-1,4-dihydropyridines that, upon visible-light absorption, can trigger the generation of acyl radicals. By means of a chiral amine catalyst, iminium ion activation of enals ensures a stereoselective radical trap. We also demonstrate how the combination of this acylation process with a second catalyst-controlled bond-forming event allows to selectively access the full matrix of all possible stereoisomers of the resulting 2,3-substituted 1,4-dicarbonyl products.

Exocyclic N-Acyliminium Ion (NAI) Cyclization: Access to Fully Substituted Oxazoles and Furocoumarins

A concise, one-pot route to oxazoles and furocoumarins has been reported. The key step in this transformation involves in situ generation of N-acyliminium ion (NAI) precursor under catalyst and solvent-free conditions and their further transformations promoted by superacid in the same pot. We have also presented the experimental evidence for the involvement of proto-solvated novel exocyclic N-acyliminium ion. Further, the UV-visible and fluorescence studies revealed that few of the compounds reported here exhibited emission of blue light upon irradiation in EtOH in the region of 404-422 nm.

Visible-light assisted one-pot preparation of aryl glyoxals from acetoarylones via in-situ arylacyl bromides formation: Selenium-free approach to acetoarylones oxidation

A novel visible-light (blue LEDs: hν?=?425?±?15?nm) photocatalyzed one-pot method for the synthesis of electronically diverse aryl glyoxals in good to excellent yields from acetoarylones and green regents such as air, vitamin C and dioxane dibromide has been described. In addition, an application of the current methodology has been demonstrated for the oxidation of monoamine oxidase-B inhibitors, i.e., 1-(4-((4-fluorobenzyl)oxy)phenyl)ethanone and 1-(3-((4-chlorobenzyl)oxy)phenyl)ethanone. This finding may serves as a valuable alternative to the traditional acetoarylones oxidation reactions conducted using selenium dioxide a harmful and unselective reagent known to simultaneously oxidize allylic, benzylic, [sbnd]CH3and so on.

Iridium-Catalyzed Asymmetric Hydrogenation of Unsaturated Piperazin-2-ones

Two different iridium catalyst systems, generated from the ruthenocene-based phosphine-oxazoline ligand tBu-mono-RuPHOX or the diphosphine ligand BINAP, were developed for the asymmetric hydrogenation of 5,6-dihydropyrazin-2(1H)-ones, affording chiral piperazin-2-ones in good yields and with moderate to good ees. Different catalytic behaviors for the hydrogenation of these types of substrate were observed with these two catalyst systems. Our tBu-mono-RuPHOX ligand, which bears a ruthenocene scaffold with planar chirality, was found to be the best ligand for the [Ir(L)(COD)]BArF catalyst system, affording the desired products with up to 94% ee. (Figure presented.).

Experimental and Theoretical Studies on Iron-Promoted Oxidative Annulation of Arylglyoxal with Alkyne: Unusual Addition and Migration on the Aryl Ring

An Fe(III)-promoted oxidative annulation reaction was developed for the synthesis of 1,2-naphthoquinones. A variety of substituted arylglyoxals and internal alkynes undergo the transformation in the presence of FeCl3 at room temperature to afford the 1,2-naphthoquinone products in good yields in a short reaction time. Interestingly, the products show unusual pseudomigration of the substituent on the arene ring of arylglyoxals. A possible mechanism involving Fe(III)-promoted formation of a vinyl cation from arylglyoxal and alkyne, electrophilic addition of the vinyl cation to the ipso carbon of the aryl group to give a spiral intermediate, and then migration of the keto carbon to the ortho carbon was proposed as key steps and verified using quantum mechanics.

Metal-free oxidative amidation of 2-oxoaldehydes: A facile access to α-ketoamides

A novel and efficient method for the synthesis of α-ketoamides, employing a dimethyl sulfoxide (DMSO)-promoted oxidative amidation reaction between 2-oxoaldehydes and amines under metal-free conditions is presented. Furthermore, mechanistic studies supported an iminium ion-based intermediate as a central feature of reaction wherein C1-oxygen atom of α-ketoamides is finally derived from DMSO.

Unexplored reactivity of 2-oxoaldehydes towards Pictet-Spengler conditions: Concise approach to β-carboline based marine natural products

Novel reactions under Pictet-Spengler conditions between tryptophan methyl ester/tryptamine and 2-oxoaldehydes have been developed and successfully utilized for the total synthesis of Merinacarboline (A and B), Eudistomin Y1, Pityriacitrin B, Pityriacitrin, Fascaplysin and analogues.

Asymmetric Hydrogenation of 2-Aryl-5,6-dihydropyrazine Derivatives with Chiral Cationic Ruthenium Diamine Catalysts

The first asymmetric hydrogenation of unfunctionalized 2-substituted and 2,3-disubstituted 5,6-dihydropyrazines catalyzed by chiral cationic Ru-diamine complex (R,R)-1a was developed, affording chiral piperazine derivatives with good enantioselectivities (up to 89% ee).