7086-13-7

Usage

Triazine derivative

A chemical compound derived from the base structure of a triazine, which is a six-membered heterocyclic ring system consisting of 3 carbon atoms and 3 nitrogen atoms.

Three phenyl groups

The presence of 3 phenyl groups (a benzene ring with a hydrogen atom replaced by a side chain) attached to the triazine ring, which contributes to the compound's structure and reactivity.

Building block for organic synthesis

2,4,6-triphenyl-1,4-dihydro-1,3,5-triazine is commonly used as a starting material for the synthesis of various organic molecules, particularly in medicinal chemistry and material science.

Unique structure and reactivity

The compound's specific arrangement of atoms and functional groups give it special properties, making it a valuable intermediate for the preparation of pharmaceuticals, agrochemicals, and advanced materials.

Electron-transporting properties

2,4,6-triphenyl-1,4-dihydro-1,3,5-triazine has the ability to move electrons through its structure, which is an important property for use in electronic devices.

Potential applications in OLEDs

Due to its electron-transporting properties, the compound has potential applications in the development of organic light-emitting diodes (OLEDs), which are used in various display technologies and lighting applications.

Upstream product

• 100-47-0 benzonitrile 
• 71-43-2 benzene 
• 493-77-6 2,4,6-triphenyl-1,3,5-triazine 
• 1670-14-0 benzamidine monohydrochloride 
• 100-52-7 benzaldehyde 
• 618-39-3 benzamidin 

Downstream Products

• 1345690-20-1 2,4,6-triphenyl-1,3,5-triazine-1-oxide 
• 493-77-6 2,4,6-triphenyl-1,3,5-triazine 
• 1345690-21-2 2-methyl-2,4,6-triphenyl-1,2-dihydro-1,3,5-triazine-1-oxide 
• 1345690-22-3 2,2,4,6-tetraphenyl-1,2-dihydro-1,3,5-triazine-1-oxide 
• 1345690-28-9 2-methyl-2,4,6-triphenyl-1,2-dihydro-1,3,5-triazinyl-1-oxy 
• 1345690-29-0 2,2,4,6-tetraphenyl-1,2-dihydro-1,3,5-triazinyl-1-oxy 

Relevant academic research and scientific papers

MCRs reshaped into a switchable microwave-assisted protocol toward 5-aminoimidazoles and dihydrotriazines

A tunable microwave-assisted protocol for the synthesis of two biologically relevant families of heterocycles has been designed. Via a simple switch of reaction conditions, the same starting materials can be engaged in either an improved synthesis of the dihydrotriazine scaffold or a novel, first-in-class MCR to render the challenging 5-aminoimidazole nucleus in a single step. An additional first-in-class MCR is also reported utilizing guanidines to afford 2,5-aminoimidazoles.

One-step synthesis of 2-amino-5h-pyrimido[5,4-b]indoles, substituted 2-(1,3,5-triazin-2-yl)-1h-indoles, and 1,3,5-triazines from aldehydes

An efficient one-step synthesis of 2-amino-5H-pyrimido[5,4-b]indoles through a copper-catalyzed cascade reaction between 3-haloindole-2-carbaldehydes and guanidine hydrochloride is described. In contrast, the base-mediated reactions of either 3-haloindole-2-carbaldehydes or substituted indole-2-carbaldehydes with substituted amidine hydrochlorides in DMSO result in the formation of 2-(1,3,5-triazin-2-yl)-1H-indole derivatives in one step in excellent yields. Studies toward exploring the utility of the method demonstrate that even substituted benzaldehydes undergo a similar reaction to efficiently yield 2,4,6-trisubstituted 1,3,5-triazines. A plausible mechanism for the formation of substituted 1,3,5-triazines identifies the role of DMSO as an oxidant during the reaction. The synthesis of 2-amino-5H-pyrimido[5,4-b]indoles from 3-haloindole-2-carbaldehyde and guanidine hydrochloride is described. In contrast, 3-haloindole-2-carbaldehydes or indole-2-carbaldehydes react with substituted amidine hydrochlorides to give 2-(1,3,5-triazin-2-yl)-1H-indole derivatives in excellent yields. The latter protocol was used to prepare 2,4,6-trisubstituted 1,3,5-triazines.

1,2-Dihydrotriazinyl-N-oxy free radicals

Triazinyl-N-oxy free radicals, 2-methyl-2,4,6-triphenyl-1,2-dihydro-1,3,5- triazinyl-1-oxy (6 a), 2,2,4,6-tetraphenyl-1,2-dihydro-1,3,5-triazinyl-1-oxy (6 b), 2,2-dimethyl-4,6-diphenyl-1,2-dihydro-1,3,5-triazinyl-1-oxy (13), and 2,6-dimethyl-2,4-diphenyl-1,2-dihydro-1,3,5-triazinyl-1-oxy (14), in which the unpaired electron is delocalized over three nitrogen atoms, have been prepared and characterized. A method has been devised for introducing an N-oxide function into the triazinyl core. Then, by using a Grignard reagent, substitution α to the N-oxide group was achieved and the resulting 1,2-dihydrotriazine- N-oxide oxidized into the corresponding nitroxide. Solution EPR spectra exhibit hyperfine splitting that confirms spin delocalization over the three nitrogen atoms of the triazinyl ring. They also show that spin delocalization diminishes with increasing distance for the coupling and is largest for nitrogen N1 and weakest for N5. Free radicals 6 a and 13 are stable in the solid state and have been characterized by X-ray diffraction, but they tend to gradually degrade in solution. In the solid state, these two free radicals are arranged into antiferromagnetically exchange-coupled pairs, J=-5.2(6) for 6 a and -3.7(4) cm-1 for 13 (H=-2 JS1S2). Copyright

Photochemistry of N-heterocycles. 7: Light induced reductive ring contractions of sixmembered cyclic iminium ions

Photochemically induced reductive ring contractions, previously observed for 2,5-dihydro-1,2,4-triazines, have also been verified for 1,4-dihydropyrimidines 2a,b, the dihydro-1,2,4,5-tetrazine 9, and dihydro-1,3,5-triazines 11a,b giving rise to fivemembered fully unsaturated heterocycles (pyrroles 4a,b, imidazoles 13a,b, and triazole 10, respectively). The 1,4-dihydropyrazines 15a-j tend to decompose in acidified 2-propanol in the dark, but on irradiation they also undergo reductive ring contraction furnishing solely the 1,2,5-triarylpyrroles 16a-d rather than the (a priori also possible) isomeric 1,3,4-triarylpyrroles 17a-d. In contrast, the 3,6-diphenylpyrid-azine 18 gives the 4-isopropyl-analogue 19 in low yield upon irradiation in hydrogen chloride saturated 2-propanol. Wiley-VCH Verlag GmbH, 2000.