116856-91-8

Basic information

• Product Name: 1,2-bis(p-nitrophenylazo)stilbene
• Synonyms: 1,2-bis(p-nitrophenylazo)stilbene
• CAS NO: 116856-91-8
• Molecular Weight: 478.467
• Mol File: 116856-91-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1,2-bis(p-nitrophenylazo)stilbene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-bis(p-nitrophenylazo)stilbene(116856-91-8)
• EPA Substance Registry System: 1,2-bis(p-nitrophenylazo)stilbene(116856-91-8)

Safety Data

• Hazardous Substances Data: 116856-91-8(Hazardous Substances Data)

Upstream product

• 134-81-6 benzil 

Downstream Products

• 144511-23-9 C₃₃H₂₃N₇O₅ 
• 144511-32-0 C₃₃H₂₃N₇O₄S 
• 493-77-6 2,4,6-triphenyl-1,3,5-triazine 
• 203450-08-2 2-di(4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine 
• 23449-08-3 2-(4-bromobenzenyl)-4,6-diphenyl-1,3,5-triazine 
• 13796-93-5 2-benzyl-4,6-diphenyl-1,3,5-triazine 
• 138722-71-1 2,4-Diphenyl-6,7-dihydro-5H-cyclopentapyrimidine 
• 116856-97-4 5-(5-Methyl-isoxazol-3-yl)-2-(4-nitro-phenyl)-4,6-diphenyl-2,5-dihydro-[1,2,3,5]tetrazine 
• 116856-96-3 2,5-Bis-(4-nitro-phenyl)-4,6-diphenyl-2,5-dihydro-[1,2,3,5]tetrazine 
• 131165-50-9 6exo-ethoxycarbonyl-2,4-bis(p-nitrophenyl)-3a,6a-diphenyl-3,3a,4,5,6,6a-hexahydropyrrolo<2,3-d>-1,2,3-triazol-2-ium-3-ide 
• 121948-38-7 4-(p-Nitrophenyl)-2,6-diphenyl-1,3,4,5-thiatriazine 
• 144511-20-6 C₃₃H₂₂N₈O₇ 

Relevant articles and documents

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.