1159096-41-9

Basic information

• Product Name: 4-cyclohexyl-1-phenyl-1H-1,2,3-triazole
• Synonyms: 4-cyclohexyl-1-phenyl-1H-1,2,3-triazole
• CAS NO: 1159096-41-9
• Molecular Weight: 227.309
• Mol File: 1159096-41-9.mol

Chemical Properties

• CAS DataBase Reference: 4-cyclohexyl-1-phenyl-1H-1,2,3-triazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-cyclohexyl-1-phenyl-1H-1,2,3-triazole(1159096-41-9)
• EPA Substance Registry System: 4-cyclohexyl-1-phenyl-1H-1,2,3-triazole(1159096-41-9)

Safety Data

• Hazardous Substances Data: 1159096-41-9(Hazardous Substances Data)

Upstream product

• 931-48-6 2-cyclohexylacetylene 
• 622-37-7 Phenyl azide 
• 62-53-3 aniline 
• 6136-96-5 1-Cyclohexyl-2,2-diethoxyethanone 
• 931-51-1 cyclohexylmagnesiumchloride 

Relevant articles and documents

A Scalable Metal-, Azide-, and Halogen-Free Method for the Preparation of Triazoles

A scalable metal-, azide-, and halogen-free method for the synthesis of substituted 1,2,3-triazoles has been developed. The reaction proceeds through a 3-component coupling of α-ketoacetals, tosyl hydrazide, and a primary amine. The reaction shows outstanding functional-group tolerance with respect to both the α-ketoacetal and amine coupling partners, providing access to 4-, 1,4-, 1,5-, and 1,4,5-substituted triazoles in excellent yield. This robust method results in densely functionalised 1,2,3-triazoles that remain challenging to prepare by azide–alkyne cycloaddition (AAC, CuAAC, RuAAC) methods and can be scaled in either batch or flow reactors. Methods for the chemoselective reaction of either aliphatic amines or anilines are also described, revealing some of the potential of this novel and highly versatile transformation.

Waste-minimised copper-catalysed azide-alkyne cycloaddition in Polarclean as a reusable and safe reaction medium

Herein we report the first example of a generally useful organic reaction, namely the copper-catalysed azide-alkyne cycloaddition, performed in a Polarclean/water mixture as a reaction medium. The process is very efficient, affording in 24 out of the 26 tested cases the desired triazole in quantitative yields. Product isolation is also very convenient, since the triazoles either precipitate or form a separate liquid phase, without the need to perform chromatographic separations. Moreover, since the metal catalyst is retained in the Polarclean/water phase, the catalyst/reaction medium can be easily reused for consecutive reaction runs, without an apparent loss in efficiency. This methodology is associated with very limited waste production, as evidenced by calculated E-factors in the range 2.6-3.7.

Phosphino-Triazole Ligands for Palladium-Catalyzed Cross-Coupling

Twelve 1,5-disubtituted and fourteen 5-substituted 1,2,3-triazole derivatives bearing diaryl or dialkyl phosphines at the 5-position were synthesized and used as ligands for palladium-catalyzed Suzuki-Miyaura cross-coupling reactions. Bulky substrates wer

Copper(I) heteroleptic bis(NHC) and mixed NHC/phosphine complexes: Syntheses and catalytic activities in the one-pot sequential CuAAC reaction of aromatic amines

A series of 2-coordinate heteroleptic Cu(I) complexes of the general formula [Cu(IPr)(L)]PF6 (2-5, L = NHC or phosphine) have been synthesized via either (i) chlorido substitution by phosphine or in situ generated free NHC or (ii) the Ag-NHC transfer protocol using [CuCl(IPr)] (1) as a precursor (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene). The reactions of precursor 1 with diphosphine ligands afforded 3-coordinate heteroleptic Cu(I) complexes of the type [Cu(IPr)(L2)]PF6 (6 and 7, L2 = diphosphine). Complexes 1-7 have been subjected to a catalytic one-pot sequential CuAAC study, in which aromatic amines serve as the precursors to aryl azides. Hetero-bis(NHC) complexes 2-4 proved to be generally superior compared to their mixed NHC/phosphine counterparts 5-7. Overall, complex [Cu(Bn2-imy)(IPr)]PF6 (2), bearing the Bn 2-imy (Bn2-imy = 1,3-dibenzyl-imidazolin-2-ylidene) coligand, showed the best catalytic performance.

Click chemistry from organic halides, diazonium salts and anilines in water catalysed by copper nanoparticles on activated carbon

An easy-to-prepare, reusable and versatile catalyst consisting of oxidised copper nanoparticles on activated carbon has been fully characterised and found to effectively promote the multicomponent synthesis of 1,2,3-triazoles from organic halides, diazonium salts, and aromatic amines in water at a low copper loading.

Unsupported copper nanoparticles in the 1,3-dipolar cycloaddition of terminal alkynes and azides

Readily prepared copper nanoparticles were found to catalyse the 1,3-dipolar cycloaddition of azides and alkynes up to rates comparable to those of microwave chemistry. Both the preparation of the nanoparticles and the click reaction are carried out under mild conditions, in short reaction times and in the absence of any stabilising additive or ligand. A variety of 1,2,3-triazoles were prepared in excellent yields. A reaction mechanism was postulated on the basis of different reactivity studies and deuteration experiments. Copper(I) acetylides were demonstrated to be the real intermediate species.

Copper nanoparticles in click chemistry: an alternative catalytic system for the cycloaddition of terminal alkynes and azides

Readily prepared copper nanoparticles have been found to effectively catalyse the 1,3-dipolar cycloaddition of a variety of azides and alkynes furnishing the corresponding 1,2,3-triazoles in excellent yields. Both the preparation of the nanoparticles and