65267-36-9

Basic information

• Product Name: 3-phenyl[1,2,4]triazolo[4,3-a]pyrimidine
• CAS NO: 65267-36-9
• Molecular Formula: C₁₁H₈N₄
• Molecular Weight: 196.208
• Mol File: 65267-36-9.mol
• Article Data: 7

Chemical Properties

• Density: 1.31g/cm³
• Refractive Index: 1.717
• CAS DataBase Reference: 3-phenyl[1,2,4]triazolo[4,3-a]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-phenyl[1,2,4]triazolo[4,3-a]pyrimidine(65267-36-9)
• EPA Substance Registry System: 3-phenyl[1,2,4]triazolo[4,3-a]pyrimidine(65267-36-9)

Safety Data

• Hazardous Substances Data: 65267-36-9(Hazardous Substances Data)

Upstream product

• 65267-35-8 N-benzylidene-N'-pyrimidin-2-ylhydrazine 
• 100-52-7 benzaldehyde 
• 5281-18-5 benzaldehyde, hydrazone 
• 274-98-6 [1,2,4]triazolo[4,3-a]pyrimidine 
• 591-50-4 iodobenzene 

Downstream Products

• 55643-77-1 2-phenyl<1,2,4>triazolo<1,5-a>pyrimidine 

Relevant articles and documents

Electrochemical synthesis of 1,2,4-triazole-fused heterocycles

A reagent-free intramolecular dehydrogenative C-N cross-coupling reaction has been developed under mild electrolytic conditions. In this atom- and step-economical one-pot process, valuable 1,2,4-triazolo[4,3-a]pyridines and related heterocyclic compounds could be synthesized efficiently from commercially available aliphatic or (hetero)aromatic aldehydes and 2-hydrazinopyridines. Various functional groups are compatible with this metal- and oxidant-free protocol which can be carried out on a gram scale easily. This novel method was applied to the synthesis of one of the top-selling drugs Xanax and late stage functionalization for generating chemical diversity in biologically relevant lead molecules.

Molecular Engineering of Mechanochromic Materials by Programmed C-H Arylation: Making a Counterpoint in the Chromism Trend

The development of facile methods for screening organic functional molecules through C-H bond activation is a revolutionary trend in materials research. The prediction of mechanochromism as well as mechanochromic trends of luminogens is an appealing yet challenging puzzle. Here, we present a strategy for the design of mechanochromic luminogens based on the dipole moment of donor-acceptor molecules. For this purpose, a highly efficient route to 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidines (2,7-diaryl-TAPs) has been established through programmed C-H arylation, which unlocks a great opportunity to rapidly assemble a library of fluorophores for the discovery of mechanochromic regularity. Molecular dipole moment can be employed to explain and further predict the mechanochromic trends. The 2,7-diaryl-TAPs with electron-donating groups on the 2-aryl and electron-withdrawing groups on the 7-aryl possess a relatively small dipole moment and exhibit a red-shifted mechanochromism. When the two aryls are interchanged, the resulting luminogens have a relatively large dipole moment and display a blue-shifted mechanochromism. Seven pairs of isomers with opposite mechanochromic trends are presented as illustrative examples. The aryl-interchanged congeners with a bidirectional emission shift are structurally similar, which provides an avenue for understanding in-depth the mechanochromic mechanism.

Palladium-catalyzed triazolopyridine synthesis: Synthesis of 7-chloro-3-(2-chlorophenyl)-1,2,4-triazolo[4,3-a]pyridine

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