82701-51-7

Basic information

• Product Name: 5-STYRYL-2H-1,2,3,4-TETRAAZOLE
• Synonyms: 5-STYRYL-2H-1,2,3,4-TETRAAZOLE;5-[2-Phenylethenyl]-2H-tetraazole
• CAS NO: 82701-51-7
• Molecular Formula: C₉H₈N₄
• Molecular Weight: 172.19
• Mol File: 82701-51-7.mol

Chemical Properties

• Melting Point: 185-187°C
• Appearance: /
• CAS DataBase Reference: 5-STYRYL-2H-1,2,3,4-TETRAAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-STYRYL-2H-1,2,3,4-TETRAAZOLE(82701-51-7)
• EPA Substance Registry System: 5-STYRYL-2H-1,2,3,4-TETRAAZOLE(82701-51-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 82701-51-7(Hazardous Substances Data)

Upstream product

• 13372-81-1 cinnamaldoxime 
• 104-55-2 3-phenyl-propenal 
• 4360-47-8 cinnamonitrile 

Downstream Products

• 1172607-42-9 C₂₃H₂₂FN₃O 

Relevant articles and documents

Igneous rock powder as a heterogeneous multi-oxide nano-catalyst for the synthesis of 5-substituted-1H-tetrazoles in polyethylene glycol

The use of igneous rock nano-powder as a heterogeneous and recyclable multi-oxide nano-catalyst synthesizing of 5-substituted-1H-tetrazoles is reported. The igneous rock nano-powder was initially prepared by using the ball-milling method. Then, the structure, morphology, and magnetic properties of the prepared igneous rock nano-powder were characterized with some different spectroscopic, microscopic, and thermogravimetric techniques, such as FTIR, FESEM, XRF, XRD, Histogram, and EDS. The instrumental analyses showed that the prepared igneous rock powder is a mixture of metal oxides, such as Si, Al, Ca, Mg, Fe, Na, Mn, and Sr. It showed an excellent catalytic performance in synthesizing of 5-substituted-1H-tetrazoles through [3 + 2] cycloaddition reaction between sodium azide and nitrile compounds. Various aliphatic and aromatic nitriles and sodium azide were reacted in the presence of a catalytic amount of igneous rock nano-powder at 80 o C temperature in PEG-400. The protocol was simple and rapid, with suitable yields of the obtained tetrazoles. The igneous rock nano-powder is readily accessible, reusable, and holds potential for further application in acid-catalyzed organic syntheses and industrial requirements. Graphic abstract: [Figure not available: see fulltext.]

Magnetic nitrogen-doped carbon derived from silk cocoon biomass: a promising and sustainable support for copper

In this study, a magnetic nitrogen-doped carbon-based copper (MNC-Cu) catalyst was fabricated so that natural silk cocoons undergo thermal processes and then activate by combining with Fe3O4 MNPs as a suitable substrate for placement copper metal. The efficiency of the generated catalyst in the synthesis of 5-substituted 1H-tetrazole derivatives was evaluated by the [3 + 2] cycloaddition reaction of aromatic aldehydes, azide ions, and hydroxylamines. FT-IR, FE-SEM, EDS, TEM, XRD, TGA, and VSM techniques have been adopted to identify and validate this heterogeneous catalyst. The observation from EDS, elemental mapping, XRD, and FT-IR analysis confirms the immobilization of Cu metals on the MNC surface and uniform distribution of species and then no aggregation occurs during functionalization. VSM results show the magnetic feature of fabricated catalyst, and based on the leaching test, the amount of catalyst leaching was negligible. Moreover, this reaction is a one-pot multicomponent reaction (MCRs) or more precisely a one-pot, three-component reaction, which is one of the advantages of this work. The fabricated catalyst shows high efficiency, good stability, and considerable reactivity in synthesizing 5-substituted 1H-tetrazole derivatives. So it can be seen that the fabricated magnetic catalyst is a useful and practical catalyst for synthesizing [3 + 2] cycloaddition reactions. Reusability and recyclability for five sequential runs without notable increase and reduction in activity are other advantages. In addition, the magnetic properties of this heterogeneous catalyst led to easy and quickly recovered and striking copper leaching. Graphical abstract: [Figure not available: see fulltext.]

Catalytic Synthesis of 5-Substituted Tetrazoles: Unexpected Reactions and Products

Tetrazoles are incredibly useful organic molecules with a wide range of applications from medicinal chemistry as carboxylic acid isosteres to high energy density materials in space research. In an effort to develop an easy protocol for the synthesis of te

One pot three-component synthesis of 5-substituted 1H-tetrazole from aldehyde

A versatile, robust and efficient strategy for the synthesis of vast range of highly functionalized 5-substituted 1H-tetrazole derivatives by using one pot three-component synthesis from various aldehydes, hydroxylamine hydrochloride and sodium azide in p

Choline chloride–ZnCl2: Recyclable and efficient deep eutectic solvent for the [2+3] cycloaddition reaction of organic nitriles with sodium azide

Herein we report first time choline chloride–zinc chloride based deep eutectic solvent is a green and efficient reaction medium for the [2+3] cycloaddition reaction of organic nitriles with sodium azide to afford the corresponding 5-substituted 1H-tetrazo

Diisopropylethylammonium acetate (DIPEAc): An efficient and recyclable catalyst for the rapid synthesis of 5-substituted-1H-tetrazoles

A simple and efficient protocol developed for the synthesis of 5-substituted 1H-tetrazole derivatives through [2+3] cycloaddition reaction between benzonitriles and sodium azide using diisopropylethylammonium acetate as a recyclable reaction medium is described. The reactions proceed well at 80 °C and provide the corresponding tetrazoles in good to excellent yields (up to 94% yield). Developed method has notable advantages, such as simple and mild conditions, easy workup, reusability with consistent catalytic activity, and safer alternative to hazardous, corrosive conventional Lewis acid catalysts.

Microwave Synthesis of 5-Substituted 1 H-Tetrazoles Catalyzed by Bismuth Chloride in Water

(Chemical Equation Presented). Bismuth chloride was used to catalyze the [2 + 3] cycloaddition between sodium azide with aryl nitriles, aliphatic nitriles, and vinyl nitriles. A number of 5-substituted 1H-tetrazoles were synthesized in water or isopropano

Preparation of 5-substituted 1H-tetrazoles catalyzed by scandium triflate in water

Several 5-substituted 1H-tetrazoles were prepared in water or isopropanol/water mixtures using microwave heating. Good yields were obtained for the [2 + 3] cycloaddition of sodium azide with aryl nitriles, aliphatic nitriles, and vinyl nitriles when catal

Multi-component one-pot reaction of aldehyde, hydroxylamine and sodium azide catalyzed by Cu-MCM-41 nanoparticles: A novel method for the synthesis of 5-substituted 1H-tetrazole derivatives

A simple and efficient procedure for the synthesis of 5-substituted 1H-tetrazole derivatives has been developed using a one-pot, three-component reaction of various aldehydes, hydroxylamine and sodium azide in the presence of a catalytic amount of Cu-MCM-41, as a nanostructured, heterogeneous and reusable catalyst. In this research, Cu-MCM-41 nanoparticles with three Cu/Si molar ratios were prepared and characterized using various techniques. The characterization and optimization results show that the catalyst with a Cu/Si molar ratio of 0.050 has the best catalytic activity.

A novel method for the synthesis of 5-substituted 1H-tetrazole from oxime and sodium azide

A simple and efficient protocol is developed for the synthesis of 5-substituted 1H-tetrazoles from various oximes and sodium azide (NaN 3) by using copper acetate as a catalyst.