87736-82-1

Usage

Uses

Used in Organic Synthesis:
3-(4-Methylphenyl)-3-(trifluoromethyl)diaziridine is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure allows it to participate in a range of chemical reactions, such as cycloadditions, rearrangements, and cross-coupling reactions, enabling the synthesis of complex organic molecules with potential applications in pharmaceuticals, agrochemicals, and materials science.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-(4-Methylphenyl)-3-(trifluoromethyl)diaziridine is used as a key building block for the development of novel drug candidates. Its ability to form diverse chemical entities makes it a valuable component in the design and synthesis of new therapeutic agents with improved pharmacological properties, such as enhanced potency, selectivity, and bioavailability.
Used in Agrochemical Industry:
3-(4-Methylphenyl)-3-(trifluoromethyl)diaziridine is also utilized in the agrochemical industry as a precursor for the synthesis of innovative agrochemicals, such as pesticides and herbicides. Its unique structural features can be exploited to create new molecules with improved efficacy, selectivity, and environmental compatibility, addressing the growing demand for sustainable agricultural practices.
Used in Materials Science:
In the field of materials science, 3-(4-Methylphenyl)-3-(trifluoromethyl)diaziridine is employed as a component in the development of advanced materials with specific properties, such as high thermal stability, chemical resistance, and unique optical or electronic characteristics. Its incorporation into polymers, coatings, and other materials can lead to the creation of novel materials with potential applications in various industries, including aerospace, automotive, and electronics.

InChI:InChI=1/C9H9F3N2/c1-6-2-4-7(5-3-6)8(13-14-8)9(10,11)12/h2-5,13-14H,1H3

Upstream product

• 87736-79-6 C₁₆H₁₄F₃NO₃S 
• 87736-79-6 2,2,2-trifluoro-1-(4-methylphenyl)-1-ethanone O-(p-tolylsulfonyl)oxime 
• 87736-79-6 2,2,2-trifluoro-1-(4-methylphenyl)-1-ethanone O-(p-toulenesulfonyl) oxime 
• 394-59-2 2,2,2-trifluoro-1-(p-tolyl)ethanone 
• 75703-25-2 2,2,2-trifluoro-1-(4-methylphenyl)-1-ethanone oxime 
• 106-38-7 para-bromotoluene 
• 75703-25-2 2,2,2-trifluoro-1-(4-methylphenyl)-1-ethanone oxime 

Downstream Products

• 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) 
• 87736-89-8 1-<<4-<3-(trifluoromethyl)-3H-diazirin-3-yl>benzoyl>oxy>-2,5-pyrrolidinedione 
• 204978-54-1 C₉H₅⁽³⁾H₂F₃N₂O 
• 204978-55-2 C₉H₄⁽³⁾H₂BrF₃N₂ 
• 204978-53-0 4-(3-Trifluoromethyl-3H-diazirin-3-yl)-benzoyl fluoride 
• 87736-88-7 3-[4-(hydroxymethyl)phenyl]-3-trifluoromethyl-3H-diazirine 

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

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

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 pharmacological evaluation of fluorescent and photoactivatable analogues of antiplasmodial naphthylisoquinolines

The naphthylisoquinoline (NIQ) alkaloids from tropical Ancistrocladaceae and Dioncophyllaceae plants show high antiplasmodial activities in vitro and in vivo, even against chloroquine-resistant strains of the malaria pathogen. For the directed optimization of these activities, an investigation of the mode of action seems most rewarding. We have therefore embarked on the identification of the respective target protein in Plasmodium falciparum. For this purpose, we have developed a flexible pathway for the synthesis of a chemically divergent series of photoactive and fluorescent derivatives of such alkaloids and succeeded in preparing the first functionalized NIQ derivatives, 10, 12, and 35, suited for fluorescence and photoaffinity labeling experiments. Pharmacological investigations ensured that the modified alkaloid derivatives retained their antiplasmodial activity. The work may pave the way for a further improvement of the activity of these natural products and will thus increase their pharmacological potential as a valuable lead structure against the widespread tropical disease malaria.

Grafting organic and biomolecules on H-terminated porous silicon from a diazirine

A diazirine compound, 1,4-(1-azi-2,2,2-trifluoroethyl)benzoic acid, was used as a stable carbene precursor to react with Si-H terminated porous silicon (PSi) under microwave irradiation. After formation of a molecular monolayer, the end carboxyl group was

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.