59066-81-8

Basic information

• Product Name: 4-(4-methylphenyl)-2H-1,2,3-triazole
• Synonyms: 4-(4-methylphenyl)-2H-1,2,3-triazole
• CAS NO: 59066-81-8
• Molecular Weight: 159.191
• Mol File: 59066-81-8.mol

Chemical Properties

• Boiling Point: 348.9±11.0 °C(Predicted)
• Density: 1.172±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 4-(4-methylphenyl)-2H-1,2,3-triazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-methylphenyl)-2H-1,2,3-triazole(59066-81-8)
• EPA Substance Registry System: 4-(4-methylphenyl)-2H-1,2,3-triazole(59066-81-8)

Safety Data

• Hazardous Substances Data: 59066-81-8(Hazardous Substances Data)

Upstream product

• 622-97-9 1-ethenyl-4-methylbenzene 
• 766-97-2 4-n-methylphenylacetylene 
• 817-87-8 ethyl azidocarbonate 
• 7559-36-6 4-methyl-β-nitrostyrene 
• 75-52-5 nitromethane 
• 104-87-0 4-methyl-benzaldehyde 

Downstream Products

• 1198612-93-9 C₉H₈BrN₃ 
• 1211548-52-5 (1S,2R)-(+)-2-phenyl-1-p-tolylcyclopropanecarbaldehyde 
• 1369584-34-8 1-(4-methyl-1,1-diphenylpent-4-en-2-ynyl)-4-p-tolyl-2H-1,2,3-triazole 
• 1369584-33-7 1-(4-methyl-1,1-diphenylpenta-1,2,4-trien-3-yl)-4-p-tolyl-2H-1,2,3-triazole 
• 1369584-32-6 2-(4-methyl-1,1-diphenylpent-4-en-2-ynyl)-4-p-tolyl-2H-1,2,3-triazole 
• 1369584-31-5 2-(4-methyl-1,1-diphenylpenta-1,2,4-trien-3-yl)-4-p-tolyl-2H-1,2,3-triazole 
• 1369584-11-1 2-(1-(trimethylsilyl)-3,3-diphenylpropa-1,2-dienyl)-4-p-tolyl-2H-1,2,3-triazole 
• 1369584-12-2 1-(1-(trimethylsilyl)-3,3-diphenylpropa-1,2-dienyl)-4-p-tolyl-1H-1,2,3-triazole 
• 1369584-44-0 1-(3-(4-chlorophenyl)-1-(trimethylsilyl)-3-phenylpropa-1,2-dienyl)-4-p-tolyl-2H-1,2,3-triazole 
• 1369584-43-9 2-(3-(4-chlorophenyl)-1-(trimethylsilyl)-3-phenylpropa-1,2-dienyl)-4-p-tolyl-2H-1,2,3-triazole 
• 1369584-35-9 2-(1-cyclopropyl-3,3-diphenylpropa-1,2-dienyl)-4-p-tolyl-2H-1,2,3-triazole 
• 1369584-36-0 1-(1-cyclopropyl-3,3-diphenylpropa-1,2-dienyl)-4-p-tolyl-1H-1,2,3-triazole 

Relevant articles and documents

A [3+2] cycloaddition-1,2-acyl migration-hydrolysis cascade for regioselective synthesis of 1,2,3-triazoles in water

A cascade sequence involving [3+2] cycloaddition, 1,2-acyl migration and hydrolysis produces 2H-1,2,3-triazolesviathe regioselective formation ofN2-carboxyalkylated triazoles. The reaction proceeds in aqueous media through intriguing reaction kinetics using a CuI-prolinamide catalyst system. Prolinamide promotes the novel organocatalytic 1,2-acyl migration as well as hydrolysis of the resultingN2-carboxyalkylated triazoles.

Synthesis and biological evaluation of selective survivin inhibitors derived from the MX-106 hydroxyquinoline scaffold

The survivin (BIRC5) expression is very low in normal differentiated adult tissues, but it is one of the most widely upregulated genes in tumor cells. The overexpression of survivin in many cancer types has been positively correlated with resistance to chemotherapy, tumor metastasis, and poor patient survival. Survivin is considered to be a cancer specific biomarker and serves as a potential cancer drug target. In this report, we describe the design and syntheses of a series of novel selective survivin inhibitors based on the hydroxyquinoline scaffold from our previously reported lead compound MX-106. The best compound identified in this study is compound 12b. In vitro, 12b inhibited cancer cell proliferation with an average IC50 value of 1.4 μM, using a panel of melanoma, breast, and ovarian cancer cell lines. The metabolic stability of 12b improved over MX-106 by 1.7-fold (88 vs 51 min in human microsomes). Western blot analyses demonstrated that treatments with 12b selectively decreased survivin protein levels, but negligibly affected other closely related members in the IAP family proteins, and strongly induced cancer cell apoptosis. In vivo, compound 12b effectively inhibited melanoma tumor growth when tested using a human A375 melanoma xenograft model. Further evaluation using an aggressive, orthotopic ovarian cancer mouse model showed that 12b was highly efficacious in suppressing both primary tumor growth in ovaries and tumor metastasis to multiple peritoneal organs. Collectively, results in this study strongly suggest that the hydroxyquinoline scaffold, represented by 12b and our earlier lead compound MX-106, has abilities to selectively target survivin and is promising for further preclinical development.

p-Toluenesulfonic acid-promoted autocatalytic hydrolyzation of 1-tosyl-1,2,3-triazoles

The first example of autocatalytic hydrolyzation of 4-aryl-1-tosyl-1,2,3-triazoles induced by p-toluenesulfonic acid was reported, providing an effective and metal-free synthetic approach to deliver a broad range of new 4-aryl-2H-1,2,3-triazoles in good yields. The kinetic profile of this hydrolyzation suggested that this reaction has exponential autocatalytic behavior.

Metal-free, highly regioselective sulfonylation of NH-1,2,3-triazoles with sodium sulfinates and thiosulfonates

A convenient and metal-free protocol for the highly regioselective sulfonylation of NH-1,2,3-triazoles is described. A range of readily accessible NH-1,2,3-triazoles were sulfonylated with various aryl sulfinates in the presence of molecular iodine. The scope was extended to thiosulfonates as an efficient sulfonylating agent and nitrochromene derived triazoles were also explored for selective N-sulfonylation. A variety of synthetically viable N2-sulfonyl triazoles were obtained in moderate to high yields with excellent regioselectivities via N–S bond construction under mild reaction conditions.

A NH - 1, 2, 3 - triazole synthetic method

The invention discloses a method for synthesizing NH-1,2,3-triazole shown by a formula (I). Under the catalytic action of a Lewis acid catalyst, nitroalkene shown by a formula (II) and hydrazoic acid salt undergo 1,3-dipolar cycloaddition, wherein Ar is p

Method for synthesizing NH-1,2,3-triazole in steps by utilizing catalysis of aluminium salt

The invention relates to a method for synthesizing NH-1,2,3-triazole in steps by utilizing the catalysis of aluminium salt, and belongs to the technical field of organic and pharmaceutical synthesis. The method is characterized in that under the catalysis of an aluminium salt catalyst, nitroolefin and sodium azide react in a 1,3-dipolar cycloaddition reaction, wherein the nitroolefin is aryl or aryl-substituted nitroolefin. The method has the following beneficial effects: the method adopts cheap and easily obtained AlCl3, Al2O3 or Al2(SO4)3 as a catalyst; aluminium ions activate nitryl of the nitroolefin, which enables the reaction to be conducted more easily under mild conditions, the yield of the reaction is improved, and an NH-1,2,3-triazole compound is conveniently and efficiently synthesized; compared with the existing methods, the method provided by the invention has the advantages of mild reaction conditions, short reaction time, good safety, convenient operation, high reaction efficiency and low-cost catalyst, and is a method of potential application value.

Aluminium(III) Chloride-Catalyzed Three-Component Condensation of Aromatic Aldehydes, Nitroalkanes and Sodium Azide for the Synthesis of 4-Aryl-NH-1,2,3-triazoles

An aluminium(III) chloride-catalyzed three-component reaction of aromatic aldehydes, nitroalkanes, and sodium azide has been developed; this reaction sequence can be applied to a broad substrate scope and affords the corresponding 4-aryl-NH-1,2,3-triazoles in good to excellent yields. The milder reaction conditions and easier operation make this AlCl3-catalyzed protocol more advantageous for the synthesis of 4-aryl-NH-1,2,3-triazoles. (Figure presented.).

Synthesis method of NH-1,2,3-triazole compound

The invention relates to a synthesis method of an NH-1,2,3-triazole compound and belongs to the technical field of organic and drug synthesis. In the presence of a Lewis acid catalyst, the NH-1,2,3-triazole compound is prepared from aromatic aldehyde, nitro-hydrocarbon and sodium azide by adopting a one-pot process. The synthesis method of the NH-1,2,3-triazole compound has the beneficial effects that available Lewis acids such as AlCl3 are taken as the catalyst, one-pot reaction is carried out on aromatic aldehyde, a nitro-hydrocarbon compound containing alpha hydrogen (wherein hydrocarbon is C1-C6 alkyls, C1-C6 alkoxys or ethyl formate) and sodium azide, reaction conditions are mild, yield is high, raw materials are available, the NH-1,2,3-triazole compound is conveniently and effectively synthesized, and compared with an existing method, the synthesis method provided by the invention is mild in reaction conditions, short in reaction time, good in safety, simple in operation, wide in substrate range and high in reaction efficiency and adopts a cheap catalyst, so that the synthesis method provided by the invention has potential application value.

Reaction between Azidyl Radicals and Alkynes: A Straightforward Approach to NH-1,2,3-Triazoles

Reaction between nitrogen-centered radicals and unsaturated C-C bonds is an effective synthetic strategy for the construction of nitrogen-containing molecules. Although the reactions between nitrogen-centered radicals and alkenes have been studied extensively, their counterpart reactions with alkynes are extremely rare. Herein, the first example of reactions between azidyl radicals and alkynes is described. This reaction initiated an efficient cascade reaction involving inter-/intramolecular radical homolytic addition toward a C-C triple bond and a hydrogen-atom transfer step to offer a straightforward approach to NH-1,2,3-triazoles under mild reaction conditions. Both the internal and terminal alkynes work well for this transformation and some heterocyclic substituents on alkynes are compatible. This mechanistically distinct strategy overcomes the inherent limitations associated with azide anion chemistry and represents a rare example of reactions between a nitrogen-centered radicals and alkynes.

Bromo-directed N-2 alkylation of NH-1,2,3-triazoles: Efficient synthesis of poly-substituted 1,2,3-triazoles

"Chemical Equation Presented" Reaction of 4-bromo-NH-1,2,3- triazoles 2 with alkyl halides In the presence of K2CO3 in DMF produced the corresponding 2-substituted 4-bromo1,2,3-triazoles 5 In a regioselective process. Subsequent Suzuki cross-coupling reaction of these bromides provided an efficient synthesis of 2,4,5-trisubstituted triazoles 3. In addition, reduction of the bromotriazoles by hydrogenation furnished an efficient synthesis of 2,4-disubstituted triazoles 8.