40618-96-0

Usage

Uses

Used in Chemical Synthesis:
3-(TrifluoroMethyl)-3-phenyldiaziridine is used as an intermediate in the synthesis of diazirine photophores for photoaffinity labeling. This application is crucial in the field of molecular biology and biochemistry, as it helps researchers understand the structure and function of proteins and other biomolecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 3-(TrifluoroMethyl)-3-phenyldiaziridine plays a significant role in the development of new drugs and therapies. 3-(TrifluoroMethyl)-3-phenyldiaziridine's ability to be used in photoaffinity labeling allows researchers to study the interactions between potential drug candidates and their target molecules, leading to the design of more effective and targeted treatments.
Used in Biochemical Research:
3-(TrifluoroMethyl)-3-phenyldiaziridine is also utilized in biochemical research to investigate the binding sites and mechanisms of action of various biomolecules. By employing photoaffinity labeling techniques, scientists can gain valuable insights into the structure and function of proteins, enzymes, and other macromolecules, which can be instrumental in the development of new therapeutic strategies and drug design.

Upstream product

• 40618-87-9 C₁₅H₁₂F₃NO₃S 
• 655-25-4 2,2,2-trifluoroacetophenone oxime 
• 434-45-7 2,2,2-Trifluoroacetophenone 

Downstream Products

• 73899-14-6 3-phenyl-3-(trifluoromethyl)-3H-diazirine 
• 434-45-7 2,2,2-Trifluoroacetophenone 

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.

Photodecarboxylative Amination of Redox-Active Esters with Diazirines

Diazirines have been recently demonstrated to serve as electrophilic amination reagents that afford diaziridines, versatile heterocycles that are readily transformed into amines, hydrazines, and nitrogen-containing heterocycles. Here, we report the photodecarboxylative amination of redox-active esters with diazirines using inexpensive photoactivators under mild conditions with an enhanced scope for primary substrates. The stability of diazirines to blue light is demonstrated, paving the way for further research into other photochemical amination methods with these unique heterocycles.

Decarboxylative Amination: Diazirines as Single and Double Electrophilic Nitrogen Transfer Reagents

The ubiquity of nitrogen-containing small molecules in medicine necessitates the continued search for improved methods for C-N bond formation. Electrophilic amination often requires a disparate toolkit of reagents whose selection depends on the specific structure and functionality of the substrate to be aminated. Further, many of these reagents are challenging to handle, engage in undesired side reactions, and function only within a narrow scope. Here we report the use of diazirines as practical reagents for the decarboxylative amination of simple and complex redox-active esters. The diaziridines thus produced are readily diversifiable to amines, hydrazines, and nitrogen-containing heterocycles in one step. The reaction has also been applied in fluorous phase synthesis with a perfluorinated diazirine.

PROCESSES AND COMPOUNDS FOR THE DECARBOXYLATIVE AMINATION OF REDOX-ACTIVE ESTERS WITH DIAZIRINES

The invention described herein relates generally to processes for the synthesis of amine-containing organic compounds. More specifically, described herein relates to processes for the decarboxylative amination of redox-active esters with diazirines and the products formed thereof. Compounds for use in the above processes are also described.

Synthesis of diaziridines and diazirines via resin-bound sulfonyl oximes

Diazirines are one of the most prominent functionalities in labeling experiments in vivo and in vitro because they allow photochemical generation of carbenes. The strategy presented herein describes the formation of diaziridines, being essential precursors in diazirine syntheses, using solid-supported procedures with immobilized sulfonyl oximes. The solid-supported building blocks have been shown to be valuable intermediates for CuAAC and amidation reactions, offering the possibility to build complex compounds with diverse functionalities.