87736-79-6

Usage

Uses

Used in Organic Synthesis:
2,2,2-Trifluoro-1-(4-methylphenyl)-O-[(4-methylphenyl)sulfonyl]oxime ethanone is used as a synthetic intermediate in the chemical industry for the preparation of various organic compounds. Its unique structure allows it to serve as a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,2,2-Trifluoro-1-(4-methylphenyl)-O-[(4-methylphenyl)sulfonyl]oxime ethanone is used as a key intermediate in the synthesis of drug candidates. Its presence in the molecular structure can impart specific biological activities, such as anti-inflammatory, analgesic, or antipyretic properties, making it a valuable component in the development of new medications.
Used in Agrochemical Industry:
2,2,2-Trifluoro-1-(4-methylphenyl)-O-[(4-methylphenyl)sulfonyl]oxime ethanone is also utilized in the agrochemical industry as a precursor for the synthesis of various agrochemicals, such as pesticides and herbicides. Its unique chemical properties can contribute to the development of more effective and environmentally friendly agrochemical products.
Used in Specialty Chemicals:
In the specialty chemicals sector, 2,2,2-Trifluoro-1-(4-methylphenyl)-O-[(4-methylphenyl)sulfonyl]oxime ethanone is employed as a component in the synthesis of various specialty chemicals, such as dyes, fragrances, and flavoring agents. Its unique structure can provide specific properties that enhance the performance and quality of these specialty products.

InChI:InChI=1/C16H14F3NO3S/c1-11-3-7-13(8-4-11)15(16(17,18)19)20-23-24(21,22)14-9-5-12(2)6-10-14/h3-10H,1-2H3/b20-15-

Upstream product

• 106-38-7 para-bromotoluene 
• 108-88-3 toluene 
• 394-59-2 2,2,2-trifluoro-1-(p-tolyl)ethanone 
• 75703-25-2 2,2,2-trifluoro-1-(4-methylphenyl)-1-ethanone oxime 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 870562-44-0 3-(3-methylphenyl)-3-trifluoromethyl-3H-diazirine 
• 87736-89-8 1-<<4-<3-(trifluoromethyl)-3H-diazirin-3-yl>benzoyl>oxy>-2,5-pyrrolidinedione 
• 1400565-49-2 N,N'-([4-(2-{4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzamido}ethyl)-1,2-phenylene]bis(oxyethane-2,1-diyloxyethane-2,1-diyl))bis{4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzamide} 
• 1400565-39-0 N,N',N''-[benzene-1,3,5-triyltris(oxyethane-2,1-diyloxyethane-2,1-diyl)]tris{4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzamide} 
• 1400565-40-3 N,N',N''-(2,2',2''-(2,2',2''-(2,2',2''-(benzene-1,3,5-triyltris(oxy))tris(ethane-2,1-diyl))tris(oxy)tris(ethane-2,1-diyl))tris(oxy)tris(ethane-2,1-diyl))tris(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzamide) 
• 1400565-50-5 N,N'-(2,2'-(2,2'-(2,2'-(4-(2-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzamido)ethyl)-1,2-phenylene)bis(oxy)bis(ethane-2,1-diyl))bis(oxy)bis(ethane-2,1-diyl))bis(oxy)bis(ethane-2,1-diyl))bis(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzamide) 
• 92367-11-8 3-[4'-(bromomethyl)phenyl]-3-(trifluoromethyl)-3H-diazirine 
• 882429-62-1 2-[(3R,4S,5S,8S,9S,10S,11R,13R,14S,16S)-16-Acetoxy-3,11-dihydroxy-4,8,10,14-tetramethyl-hexadecahydro-cyclopenta[a]phenanthren-(17Z)-ylidene]-6-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-hexanoic acid 2,2-dimethyl-propionyloxymethyl ester 
• 882429-59-6 2-(16-acetoxy-3,11-dihydroxy-4,8,10,14-tetramethyl-hexadecahydro-cyclopenta[a]phenanthren-17-ylidene)-6-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-hex-5-enoic acid 2,2-dimethyl-propionyloxymethyl ester 

Relevant academic research and scientific papers

Photochemical Cyclopropenation of Alkynes with Diazirines as Carbene Precursors in Continuous Flow

An efficient synthesis of 3-trifluoromethyl-3-aryl-cyclopropenes via the cyclopropenation reaction of alkynes with photolytically generated carbenes from diazirine compounds is described. This reaction is performed in continuous flow using readily available LEDs under mild reaction conditions. This new and efficient method describes the synthesis of 25 examples of 3-trifluoromethyl-3-aryl-cyclopropenes with yields up to 97%, achieved in continuous flow with a 5 min residence time. Control experiments highlighted that diazirines are more efficient than diazo compounds for this transformation.

Engineering bromodomains with a photoactive amino acid by engaging 'Privileged' tRNA synthetases

Site-specific placement of unnatural amino acids, particularly those responsive to light, offers an elegant approach to control protein function and capture their fleeting 'interactome'. Herein, we have resurrected 4-(trifluoromethyldiazirinyl)-phenylalan

Rapid Mapping of Protein Interactions Using Tag-Transfer Photocrosslinkers

Analysing protein complexes by chemical crosslinking-mass spectrometry (XL-MS) is limited by the side-chain reactivities and sizes of available crosslinkers, their slow reaction rates, and difficulties in crosslink enrichment, especially for rare, transie

Click-Addressable Cassette for Photoaffinity Labeling

A small molecule 1 was designed to contain an alkyne, a trifluoromethyl phenyldiazirine, and a free piperidine-NH for facile conjugation to protein binding ligands. This "cassette" 1 was synthesized via a relatively direct route involving only routine steps. In this proof-of-concept study, putative ligands for carbonic anhydrase IX and for TrkC were conjugated to 1. Photoaffinity labeling was performed using purified extracellular regions of both these protein-receptors, and using cells that express these receptors (isolation via a pull-down procedure), labeling of the protein was observed in all four experiments.

Is Magnetic Bistability of Carbenes a General Phenomenon? Isolation of Simple Aryl(trifluoromethyl)carbenes in Both Their Singlet and Triplet States

p-Tolyl(trifluoromethyl)carbene and the related fluorenyl(trifluoromethyl)carbene were synthesized in solid argon and characterized by IR, UV-vis, and electron paramagnetic resonance spectroscopy as well as by quantum mechanical calculations. The carbenes

Alternative one-pot synthesis of (trifluoromethyl)phenyldiazirines from tosyloxime derivatives: Application for new synthesis of optically pure diazirinylphenylalanines for photoaffinity labeling

Alternative one-pot synthesis of 3-(trifluoromethyl)-3-phenyldiazirine derivatives from corresponding tosyloximes is developed. The deprotonation of intermediate diaziridine by NH2- is a new approach for construction of diazirine. Moreover, a novel synthesis of optically pure (trifluoromethyl)diazirinylphenylalanine derivatives was attempted involving these methods.

Synthesis of diazirine-based photoreactive saccharin derivatives for the photoaffinity labeling of gustatory receptors

Saccharin is one of the most common artificial sweeteners that has a bitter taste at high concentrations. Currently, there are no detailed functional analyses of these gustatory receptors. Therefore, we designed and synthesized photoreactive saccharin der

Synthesis and structure-activity relationship study of chemical probes as hypoxia induced factor-1α/malate dehydrogenase 2 inhibitors

A structure-activity relationship study of hypoxia inducible factor-1α inhibitor 3-aminobenzoic acid-based chemical probes, which were previously identified to bind to mitochondrial malate dehydrogenase 2, was performed to provide a better understanding of the pharmacological effects of LW6 and its relation to hypoxia inducible factor-1α (HIF-1α) and malate dehydrogenase 2 (MDH2). A variety of multifunctional probes including the benzophenone or the trifluoromethyl diazirine for photoaffinity labeling and click reaction were prepared and evaluated for their biological activity using a cell-based HRE-luciferase assay as well as a MDH2 assay in human colorectal cancer HCT116 cells. Among them, the diazirine probe 4a showed strong inhibitory activity against both HIF-1α and MDH2. Significantly, the inhibitory effect of the probes on HIF-1α activity was consistent with that of the MDH2 enzyme assay, which was further confirmed by the effect on in vitro binding activity to recombinant human MDH2, oxygen consumption, ATP production, and AMP activated protein kinase (AMPK) activation. Competitive binding modes of LW6 and probe 4a to MDH2 were also demonstrated.

Tri- and tetravalent photoactivable cross-linking agents

A modular synthesis of photoactivable cross-linking agents is described, using an aromatic core, di- or triethyleneglycol spacers and photoaffinity labeling synthons that feature either perfluorophenyl azide or aryl(trifluoromethyl)diazirine motifs. Symmetrical and nonsymmetrical trivalent structures were obtained from phloroglucinol and dopamine, respectively. Symmetrical tetravalent structures resulted from the coupling of two dopamine derivatives with oxalyl chloride. Georg Thieme Verlag Stuttgart New York.

Synthesis and biological evaluation of photoaffinity labeled fusidic acid analogues

Novel photoaffinity labeled fusidic acid analogues were obtained by a synthetic sequence employing a Wittig reaction between a fusidic acid aldehyde and benzyl bromides in the key step. Three commonly used photoreactive groups, benzophenone, trifluoromethyldiazirine, and aryl azide, were used. The photoaffinity labeled fusidic acid analogues demonstrated a potent antibacterial activity (MIC 0.016-4 μg/mL) and therefore represent a potential tool for the elucidation of the interactions between fusidic acid and its receptor EF-G.