939821-42-8

Basic information

• Product Name: 2-phenyl-3-(trifluorophenyl)imidazo[1,2-a]pyridine
• Synonyms: 2-phenyl-3-(trifluorophenyl)imidazo[1,2-a]pyridine
• CAS NO: 939821-42-8
• Molecular Weight: 262.234
• Mol File: 939821-42-8.mol

Chemical Properties

• CAS DataBase Reference: 2-phenyl-3-(trifluorophenyl)imidazo[1,2-a]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phenyl-3-(trifluorophenyl)imidazo[1,2-a]pyridine(939821-42-8)
• EPA Substance Registry System: 2-phenyl-3-(trifluorophenyl)imidazo[1,2-a]pyridine(939821-42-8)

Safety Data

• Hazardous Substances Data: 939821-42-8(Hazardous Substances Data)

Upstream product

• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 4105-21-9 2-phenylimidazo[1,2-a]pyridine 
• 504-29-0 2-aminopyridine 
• 887144-94-7 Togni's reagent II 
• 2314-97-8 iodotrifluoromethane 
• 2926-30-9 sodium triflate 
• 2926-29-6 Langlois reagent 
• 147531-11-1 trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt 
• 64413-90-7 3-iodo-2-phenylimidazo[1,2-α]pyridine 

Relevant articles and documents

Copper(I)-catalyzed direct C-H trifluoromethylation of imidazoheterocycles with Togni's reagent

A mild and efficient trifluoromethylation of imidazopyridines with Togni's reagent in the presence of inexpensive base has been realized at room temperature. This methodology has several advantages: (1) using efficient copper(I) as catalyst and inexpensiv

Visible-light-promoted direct C3-trifluoromethylation and perfluoroalkylation of imidazopyridines

An efficient method for direct trifluoromethylation and perfluoroalkylation at C3 of imidazopyridines through visible light-promoted C-H bond functionalization was developed. Under the irradiation of a blue LED, a series of C3-perfluoroalkyl-substituted imidazopyridines were synthesized from the corresponding imidazopyridines and perfluoroalkyl iodides in moderate to good yields at room temperature. It should be mentioned that this reaction proceeded in the absence of any transition-metal catalyst, oxidant and photocatalyst.

Electrochemically mediated trifluoromethylation of 2H-indazole derivatives using CF3SO2Na

An environmentally friendly method of electrochemical mediated regioselective C-3 trifluoromethylation of 2H-indazole by employing CF3SO2Na as the CF3 source was described. This reaction tolerated various functional groups and provided C[sbnd]H trifluoromethylated products in moderate to good yields under transition metal-free and oxidant-free reaction conditions. Mechanism experiments showed that a radical process might be involved in this transformation.

Transition metal-free direct C–H trifluoromethyltion of (hetero)arenes with Togni's reagent

A new transition-metal-free direct C–H trifluoromethylation reaction of (hetero)arenes with Togni's reagent was developed. This transformation proceeded smoothly under mild conditions and exhibited good tolerance of many synthetically relevant functional groups. It provided an alternative approach for the synthesis of trifluoromethylated (hetero)arenes.

Visible-Light-Promoted Metal-Free C-H Trifluoromethylation of Imidazopyridines

A metal-free photo redox C–H trifluorometlylation of imidazopyridines is described. The reaction is operationally simple and the easy-handling CF3SO2Na serves as an effective fluoroalkyl radical precursor. Various functional groups were tolerated under blue LED light to access the desired products in satisfied yields at room temperature.

Transition-Metal-Free Direct Trifluoromethylation and Perfluoroalkylation of Imidazopyridines under Mild Conditions

The first transition-metal-free method for direct C?H trifluoromethylation of imidazo[1,2-a]pyridine derivatives with readily available Ruppert-Prakash reagent TMSCF3 under mild conditions was described. Moreover, this method could be applied to direct C?H perfluoroalkylation of imidazopyridines, affording a series of novel perfluoroalkylated products in moderate to good yields. Notable advantages of this protocol include easy operation, high-efficiency and wide substrate scope. (Figure presented.).

Transition-metal-free, visible-light-mediated regioselective C–H trifluoromethylation of imidazo[1,2-a]pyridines

A transition-metal-free, visible-light-induced trifluoromethylation of imidazo[1,2-a]pyridines has been developed at mild conditions by employing cheap and commercially available anthraquinone-2-carboxylic acid (AQN-2-CO2H) as the photo-organocatalyst, and Langlois reagent as the trifluoromethylating reagent. A series of 3-(trifluoromethyl)imidazo[1,2-a]pyridine derivatives with broad functionalities could be conveniently and efficiently obtained by direct regioselective functionalization.

Trifluoromethylimidazole fused ring compound and preparation method thereof

The invention relates to a trifluoromethyl imidazole fused ring compound and a preparation method thereof, and belongs to the field of synthesis of imidazole fused ring compounds. The structural general formula of the trifluoromethyl imidazole fused ring compound is shown as formula I, wherein A is a five-membered heterocyclic ring or a six-membered heterocyclic ring, and B is phenyl, pyridyl or thienyl; R1 is hydrogen, alkyl, alkoxy, halogen, an ester group or trifluoromethyl; R2 is hydrogen, alkyl, alkoxy, halogen, trifluoromethyl or sulfonyl; the number of carbon atoms in the alkyl group, alkoxy group, ester group and sulfuryl group is 1-6. According to the compound, an imidazole ring and a five-membered heterocyclic ring or a six-membered heterocyclic ring are fused to form a parent; trifluoromethylation is realized at the C3 site, trifluoromethyl groups having strong electron-withdrawing induction effect and containing stable fluorocarbon bonds are introduced into the parent, so that the acidity, the dipole moment, the lipophilicity and the metabolic stability of molecules can be remarkably changed, and potential good biological activity is achieved.

Nickel-Catalyzed C–H Trifluoromethylation of Electron-Rich Heteroarenes

The first example of a nickel-catalyzed C–H trifluoromethylation of electron-rich heteroarenes, including imidazopyridines, indoles and thiophenes, has been developed with the commercially available and relatively inexpensive industrial raw material iodotrifluoromethane (CF3I) as the trifluoromethylating reagent. The synthetic potential of this method is demonstrated by its successful application to the direct trifluoromethylation of the biologically active molecules melatonin and zolmitriptan. (Figure presented.).

Photoorganocatalysed and visible light photoredox catalysed trifluoromethylation of olefins and (hetero)aromatics in batch and continuous flow

Trifluoromethylation of olefins and (hetero)aromatics with sodium triflinate as CF3 source and readily accessible benzophenone derivatives as photosensitisers has been developed in batch and flow. The use of an iridium-based photocatalyst enables the trifluoromethylation to proceed under visible light irradiation.