151451-82-0

Basic information

• Product Name: 4-butyl-1-phenyl-1H-1,2,3-triazole
• Synonyms: 4-butyl-1-phenyl-1H-1,2,3-triazole
• CAS NO: 151451-82-0
• Molecular Weight: 201.271
• Mol File: 151451-82-0.mol

Chemical Properties

• CAS DataBase Reference: 4-butyl-1-phenyl-1H-1,2,3-triazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-butyl-1-phenyl-1H-1,2,3-triazole(151451-82-0)
• EPA Substance Registry System: 4-butyl-1-phenyl-1H-1,2,3-triazole(151451-82-0)

Safety Data

• Hazardous Substances Data: 151451-82-0(Hazardous Substances Data)

Upstream product

• 1191-12-4 1-hexynyltrimethylstannane 
• 622-37-7 Phenyl azide 
• 591-50-4 iodobenzene 
• 693-02-7 hex-1-yne 
• 62-53-3 aniline 
• 66-25-1 hexanal 
• 98-80-6 phenylboronic acid 

Downstream Products

• 1111662-45-3 4-(4-n-butyl-1-phenyl-1H-1,2,3-triazol-5-yl)benzoic acid ethyl ester 
• 1037412-76-2 4-N-butyl-5-(2-methoxyphenyl)-1-phenyl-1H-1,2,3-triazole 
• 1037412-43-3 4-N-butyl-5-(4-methoxyphenyl)-1-phenyl-1H-1,2,3-triazole 
• 1127217-84-8 4-n-butyl-5-(3,5-dimethoxyphenyl)-1-phenyl-1,2,3-triazole 
• 1258275-46-5 [C₂HN₃(CH₃)(C₄H₉)C₆H₅]⁽¹⁺⁾*I^(1-)=[C₂HN₃(CH₃)(C₄H₉)C₆H₅]I 
• 1126639-47-1 4-n-butyl-1-phenyl-5-p-tolyl-1H-1,2,3-triazole 
• 1255536-59-4 methyl 4-(4-butyl-1-phenyl-1H-1,2,3-triazol-5-yl)benzoate 
• 1186493-22-0 5-benzyl-4-butyl-1-phenyl-1H-1,2,3-triazole 
• 1126639-46-0 4-n-butyl-5-(4-fluorophenyl)-1-phenyl-1H-1,2,3-triazole 
• 1126639-45-9 4-n-butyl-1,5-diphenyl-1H-1,2,3-triazole 
• 1126639-51-7 4-n-butyl-5-(3-(N,N-dimethylamino)phenyl)-1-phenyl-1H-1,2,3-triazole 

Relevant articles and documents

A palladacyclic N-heterocyclic carbene system used to probe the donating abilities of monoanionic chelators

A series of NHC-containing [C^N]- or [C^C′]-type palladacyclic complexes of the general formula [PdBr(iPr2-bimy)(L^X)] (5-8, 11, 12, iPr2-bimy = 1,3-diisopropylbenzimidazolin-2-ylidene) have been synthesized and fully characterized. Using these complexes, the donating abilities of monoanionic chelators were probed for the first time. The [C^N]-type palladacycles 5-8 were prepared from acetato-bridged dipalladium complexes [Pd(μ-CH3COO)(C^N)]2 (1-4) and iPr2-bimy·H+Br-as precursors. In the case of the [C^C′]-type NHC palladacycles (11, 12), the hetero-bis(NHC) complexes trans-[PdBr2(iPr2-bimy)(trz)] (8, 9, trz = 1,2,3-triazolin-5-ylidene) containing the iPr2-bimy probe were first prepared followed by acetate-assisted cyclopalladations. The 13Ccarbene NMR signals of the iPr2-bimy ligands in all complexes (i.e. HEP and HEP2 values) are found to rationally reflect the donating abilities of the incorporated trz or [L^X]-type chelators with the exception of the Bzpy ligand (Bzpy = 2-(2-pyridinylmethyl)phenyl-C,N). This has been attributed to its larger bite angle, the resulting varied coordination geometry and the lack of electronic delocalization between the two donor units. The donicities of [L^X]-type chelators studied in this work were found to surpass those of all other bidentate ligands evaluated by HEP2 thus far.

Silica immobilized copper N-heterocyclic carbene: An effective route to 1,2,3-triazoles via azide-alkyne cycloaddition and multicomponent click reaction

A new silica supported copper N-heterocyclic carbene (Cu-NHC@SiO2) complex is prepared and characterized by scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX) and X-ray photoelectron spectroscopy (XPS) analyses. This complex is an efficient and easily retrievable catalyst for 1,2,3-triazole synthesis through direct azide-alkyne cycloaddition reaction as well as one-pot reaction using arylboronic acids. This catalytic system is also suitable for synthesis of 4-aryl-NH-1,2,3-triazoles from diverse benzaldehydes. Further, the catalyst can efficiently be recycled up to fifth cycle for all the three methods of 1,2,3-triazole synthesis through direct azide-alkyne cycloaddition and multi-component reactions.

Using Small Molecules to Enhance P450 OleT Enzyme Activity in Situ

Cytochrome P450 OleT is a fatty acid decarboxylase that catalyzes the production of olefins with biofuel and synthetic applications. However, the relatively sluggish catalytic efficiency of the enzyme limits its applications. Here, we report the application of a novel class of benzene containing small molecules to improve the OleT activity. The UV-Vis spectroscopy study and molecular docking results confirmed the high proximity of the small molecules to the heme group of OleT. Up to 6-fold increase of product yield has been achieved in the small molecule-modulated enzymatic reactions. Our work thus sheds the light to the application of small molecules to increase the OleT catalytic efficiency, which could be potentially used for future olefin productions.

Dinuclear Cu(I) Halides with Terphenyl Phosphines: Synthesis, Photophysical Studies, and Catalytic Applications in CuAAC Reactions

Several dinuclear terphenyl phosphine copper(I) halide complexes of composition [CuX(PR2Ar′)]2 (X = Cl, Br, I; R = hydrocarbyl, Ar′ = 2,6-diarylterphenyl radical), 1-5, have been isolated from the reaction of CuX with 1 equiv of the phosphine ligand. Most

A ferrocene functionalized Schiff base containing Cu(ii) complex: Synthesis, characterization and parts-per-million level catalysis for azide alkyne cycloaddition

Atom economy is one of the major factors in developing catalysis chemistry. Using the minimum amount of catalyst to obtain the maximum product yield is of the utmost priority in catalysis, which drives us to use parts-per-million (ppm) levels of catalyst

Polysaccharide-based superporous hydrogel embedded with copper nanoparticles: A green and versatile catalyst for the synthesis of 1,2,3-triazoles

In this contribution, we a report a facile synthesis and stabilization of copper nanoparticles (CuNPs) in a superporous hydrogel based on chitosan (Cs) and poly(vinyl alcohol) (PVA). The functional groups of Cs and PVA stabilized the CuNPs and, as a result, several properties (e.g. thermal, morphological and liquid uptake) of the final materials exhibited remarkable improvements in terms of stability and catalytic activity. The metallic nature of CuNPs was confirmed by XRD and XPS analyses. From the XRD data, the Cu nanoparticle size was estimated to range from 3 to 7 nm. Moreover, EDS mapping analysis revealed that the CuNPs are homogeneously distributed throughout the hydrogel surface. The Cs/PVA-CuNP hydrogel was found to be an excellent catalyst for the synthesis of 1,2,3-triazoles using phenyl azide and phenylacetylene as model substrates under mild optimized conditions (>90% yield). Reuse studies revealed that this original CuNP-containing catalyst can be employed in at least 5 consecutive cycloaddition reactions without demonstrating a clear loss of efficiency. Moreover, the copper leaching from the hydrogel matrix was negligible during these consecutive reactions under the investigated conditions. The Cs/PVA-CuNP hydrogel could also efficiently catalyze cycloaddition reactions involving different substituted azide and alkyne precursors.

Mono- and dinuclear palladium(II) complexes incorporating 1,2,3-triazole-derived mesoionic carbenes: syntheses, solid-state structures and catalytic applications

Two 1,2,3-triazole-derived monocationic salts 3 and 4 bearing N-aryl wingtips were prepared using copper-catalyzed “click” reactions followed by alkylations with iodomethane. Employing a silver–carbene transfer method, two dinuclear palladium(II) complexes of triazolin-5-ylidenes (5/6) were obtained, the former of which has been reported previously. Bridge-cleavage reaction of 5 as a representative with PPh3 yielded cis-configured mesoionic carbene/phosphine hybrid complex cis-7 and homoleptic bis(phosphine) complex 8, suggesting the presence of a ligand exchange process. In contrast, bridge breakages of 5/6 with pyridine cleanly afforded PEPPSI-type complexes 9 and 10 in near quantitative yields. Finally, all complexes were exploited to catalyze Mizoroki–Heck coupling reactions with aryl bromides as the substrates, and PEPPSI-type complex 9 was found to be the best performer generally giving good to excellent yields.

Ag-NHC anchored on silica: An efficient ultra-low loading catalyst for regioselective 1,2,3-triazole synthesis

A silica-supported silver complex, Ag-NHC@SiO2, was prepared by an anchoring coordination technique, which was successfully employed for the click reaction under mild reaction conditions. The protocol offered the remarkable advantages of operat

Method for preparing 1,2,3-triazole compound by heterogeneous copper catalysis in one pot

The invention relates to a method for preparing a 1-aryl-4-substituted-1,2,3-triazole compound shown as a formula (II). The method comprises the following steps: mixing arylboronic acid (1), NaN3, a heterogeneous copper catalyst and solvent water, performing a stirring reaction at 25-60 DEG C for 4-8 hours, performing TLC (thin-layer chromatography) monitoring till the arylboronic acid (1) is completely converted, replacing air in the reaction system by using N2, adding a terminal alkyne (2), performing a reaction at 40-80 DEG C for 6-10 hours under the protection of N2, and performing post-treatment on the reaction solution to obtain a product (II). By adopting the preparation method, Cu-coated SBA-15-PTAA is used as a catalyst, a series of 1-aryl-4-substituted-1,2,3-triazole compounds are prepared through a one-pot Chan-Lam/Click series method without additionally adding a reducing agent, the developed catalytic method is green, safe and economical, the amount of three wastes (wastegas, waste water and industrial residue) is small, the yield of a target product is high, and the substrate application range is wide.

Synthesis of a heterogeneous Cu(OAc)2-anchored SBA-15 catalyst and its application in the CuAAC reaction

A novel dinuclear Cu(OAc)2-anchored SBA-15 catalyst was synthesized by simple proton exchange of a carboxyl functionalized mesoporous SBA-15 silica with Cu(OAc)2 in water. XAFS and EPR spectra were utilized to probe its structure. Su