13796-93-5

Usage

Class

Triazine compounds

Structure

Three nitrogen atoms in a six-membered ring
Two phenyl groups attached to the 2,4 positions
Phenylmethyl group attached to the 6 position of the triazine ring

Industrial Applications

Potential uses in pharmaceuticals
Potential uses in dyes
Potential uses in materials science

Chemical Properties

Reactivity that makes it a subject of interest for further research and development

Research and Development

May have potential for further exploration in various fields due to its unique structure and properties

Upstream product

• 116856-96-3 2,5-Bis-(4-nitro-phenyl)-4,6-diphenyl-2,5-dihydro-[1,2,3,5]tetrazine 
• 116856-91-8 1,2-bis(p-nitrophenylazo)stilbene 
• 4971-77-1 ethyl 2-phenylethanimidoate 
• 5504-24-5 2-phenylacetamidine 
• 134-81-6 benzil 
• 1670-14-0 benzamidine monohydrochloride 

Relevant academic research and scientific papers

Synthesis, characterization, and cycloaddition reactivity of a monocyclic aromatic 1,2,3,5-tetrazine

Herein we disclose the synthesis and full characterization of the first monocyclic aromatic 1,2,3,5-tetrazine, 4,6-diphenyl-1,2,3,5-tetrazine. Initial studies of its cycloaddition reactivity, mode, regioselectivity, and scope illustrate that it participates as the 4π-component of well-behaved inverse electron demand Diels-Alder reactions where it preferentially reacts with electron-rich or strained dienophiles. It was found to exhibit an intrinsic reactivity comparable to that of the isomeric 3,6-diphenyl-1,2,4,5-tetrazine, display a single mode of cycloaddition with reaction only across C4/N1 (no N2/N5 cycloaddition observed), proceed with a predictable regioselectivity (dienophile most electron-rich atom attaches to C4), and manifest additional reactivity complementary to the isomeric 1,2,4,5-tetrazines. It not only exhibits a remarkable cycloaddition reactivity, surprisingly good stability (e.g., stable to chromatography, long-term storage, presence of H2O even as reaction co-solvent), and broad cycloaddition scope, but it also displays powerful orthogonal reactivity with the 1,2,4,5-tetrazines. Whereas the latter reacts at extraordinary cycloaddition rates with strained dienophiles (tetrazine ligation), the new and isomeric 1,2,3,5-tetrazine displays similarly remarkable cycloaddition rates and efficiencies with amidines (1,2,3,5-tetrazine/amidine ligation). The crossover reactivities (1,2,4,5-tetrazines with amidines and 1,2,3,5-tetrazines with strained dienophiles) are sufficiently low to indicate they may be capable of use concurrently without competitive reactions.

APPLICATION OF SUBSTITUTED 1-ACYLAMINOETHENYLPHOSPHONIUM SALTS IN THE PREPARATION OF 1,3,5-TRIAZINE DERIVATIVES

It was shown that available phosphonium reagents with the characteristic moiety =C=C(NHCOR)P+ smoothly react with benzamidine hydrochloride and its analogs in the presence of sodium methylate with splitting of the C-P bond and formation of a