76599-37-6

Basic information

• Product Name: 1-(adamantan-1-yl)-4-phenyl-1H-[1,2,3]-triazole
• Synonyms: 1-(adamantan-1-yl)-4-phenyl-1H-[1,2,3]-triazole
• CAS NO: 76599-37-6
• Molecular Weight: 279.385
• Mol File: 76599-37-6.mol
• Article Data: 21

Chemical Properties

• CAS DataBase Reference: 1-(adamantan-1-yl)-4-phenyl-1H-[1,2,3]-triazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(adamantan-1-yl)-4-phenyl-1H-[1,2,3]-triazole(76599-37-6)
• EPA Substance Registry System: 1-(adamantan-1-yl)-4-phenyl-1H-[1,2,3]-triazole(76599-37-6)

Safety Data

• Hazardous Substances Data: 76599-37-6(Hazardous Substances Data)

Upstream product

• 24886-73-5 1-Azidoadamantane 
• 536-74-3 phenylacetylene 
• 768-90-1 1-Adamantyl bromide 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 102-96-5 (2-nitroethenyl)benzene 

Relevant articles and documents

Synthesis of adamantyl substituted 1,2,3-triazol-5-ylidene ligands and their PEPPSI-type palladium complexes

PEPPSI-type Pd-complexes with the bulky mesoionic 1,2,3-triazolium carbenes (tzNHC) substituted by the adamantyl groups were prepared from 1-azidoadamantane and 1-ethynyladamantane. The X-ray analysis revealed that 1,4-diadamantyl-tzNHC complex (TAd-PEPPSI) showed longer Pd-C bond length than 1-adamantyl-4-phenyl-tzNHC complex (TAdPh-PEPPSI) and 1,4-diphenyl-tzNHC complex (TPh-PEPPSI). These complexes were applied to Hiyama coupling reaction between aryl bromides and phenyltrimethoxysilane. TAd-PEPPSI rapidly initiates the reaction, and TAdPh-PEPPSI gave good product yields.

Assembly of four modules onto a tetraazide platform by consecutive 1,2,3-triazole formations

Efficient consecutive 1,2,3-triazole formations using multiazide platforms are disclosed. On the basis of unique clickability of the 1-adamantyl azido group, a four-step synthesis of tetrakis(triazole)s was achieved from a tetraazide platform molecule. This method was applied to a convergent synthesis of tetrafunctionalized probes in a modular synthetic manner.

Influence of steric demand on ruthenium-catalyzed cycloaddition of sterically hindered azides

The RuAAC of sterically hindered 2,2-diaryl-2-azidoamines and terminal alkynes resulted in the unprecedented formation of 1,4-disubstituted-1,2,3-triazoles. A control experiment with 2-(azidomethyl)pyrrolidine revealed the usual selectivity with RuAAC and