50907-33-0

Basic information

• Product Name: 3-(2H-TETRAZOL-5-YL)BENZONITRILE
• Synonyms: 3-(2H-TETRAZOL-5-YL)BENZONITRILE
• CAS NO: 50907-33-0
• Molecular Formula: C₈H₅N₅
• Molecular Weight: 171.16
• Mol File: 50907-33-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(2H-TETRAZOL-5-YL)BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2H-TETRAZOL-5-YL)BENZONITRILE(50907-33-0)
• EPA Substance Registry System: 3-(2H-TETRAZOL-5-YL)BENZONITRILE(50907-33-0)

Safety Data

• Hazardous Substances Data: 50907-33-0(Hazardous Substances Data)

Upstream product

• 626-17-5 benzene-1,3-dicarbonitrile 

Relevant articles and documents

Discovery, synthesis and characterization of a series of (1-alkyl-3-methyl-1H-pyrazol-5-yl)-2-(5-aryl-2H-tetrazol-2-yl)acetamides as novel GIRK1/2 potassium channel activators

The present study describes the discovery and characterization of a series of 5-aryl-2H-tetrazol-3-ylacetamides as G protein-gated inwardly-rectifying potassium (GIRK) channels activators. Working from an initial hit discovered during a high-throughput screening campaign, we identified a tetrazole scaffold that shifts away from the previously reported urea-based scaffolds while remaining effective GIRK1/2 channel activators. In addition, we evaluated the compounds in Tier 1 DMPK assays and have identified a (3-methyl-1H-pyrazol-1-yl)tetrahydrothiophene-1,1-dioxide head group that imparts interesting and unexpected microsomal stability compared to previously-reported pyrazole head groups.

A 5 - substituted four nitrogen azole compound of synthetic method (by machine translation)

The invention discloses a 5 - substituted four nitrogen azole compound of synthetic method, the synthesis method of the process is as follows: to point pen in the autoclave (I) indicated by the nitrile compounds, sodium azide, nickel ferrite and carboxylic acid ammonium ion exchange resin, added with an organic solvent to the cyclization reaction, the reaction solution after the reaction is finished filter, pickling, desolvation and heavy after crystallization, as shown in formula (II) of the 5 - substituted tetrazole compounds, yield is 85 - 95%, purity ≥ 99%; Formula (I) in the formula (II), the substituent R1 Is phenyl, substituted phenyl, C1 - C3 alkyl or amino; substituted phenyl substituent is methyl, methoxy, F or nitro. The invention of 5 - substituted tetrazole compounds synthesis method, adopt the catalytic ferrous acid nickel and carboxylic acid ammonium ion exchange resin catalyst combination, the carboxylic acid [...], not only good general the reaction substrate, the reaction yield is high, and the catalyst is easily separated and recycled, the production cost is reduced and the three waste emissions. (by machine translation)

Syntheses of 5-substituted 1H-tetrazoles catalyzed by reusable Cu(II)-NaY zeolite from nitriles

Cu(II)-NaY heterogeneous catalyst is used for the synthesis of 5-substituted 1H-tetrazoles by [2+3]-cycloaddition of sodium azide and nitriles. The salient features of this process are low reaction times, mild reaction conditions and high yields. The catalyst is recovered and reused for several cycles with consistent activity.

One-pot synthesis of 1- and 5-substituted 1H-tetrazoles using 1,4-dihydroxyanthraquinone–copper(II) supported on superparamagnetic Fe3O4@SiO2 magnetic porous nanospheres as a recyclable catalyst

An effective one-pot, convenient process for the synthesis of 1- and 5-substituted 1H-tetrazoles from nitriles and amines is described using1,4-dihydroxyanthraquinone–copper(II) supported on Fe3O4@SiO2 magnetic porous nanospheres as a novel recyclable catalyst. The application of this catalyst allows the synthesis of a variety of tetrazoles in good to excellent yields. The preparation of the magnetic nanocatalyst with core–shell structure is presented by using nano-Fe3O4 as the core, tetraethoxysilane as the silica source and poly(vinyl alcohol) as the surfactant, and then Fe3O4@SiO2 was coated with 1,4-dihydroxyanthraquinone–copper(II) nanoparticles. The new catalyst was characterized using Fourier transform infrared spectroscopy, X-ray diffraction, transmission electron microscopy, field emission scanning electron microscopy, dynamic light scattering, thermogravimetric analysis, vibration sample magnetometry, X-ray photoelectron spectroscopy, nitrogen adsorption–desorption isotherm analysis and inductively coupled plasma analysis. This new procedure offers several advantages such as short reaction times, excellent yields, operational simplicity, practicability and applicability to various substrates and absence of any tedious workup or purification. In addition, the excellent catalytic performance, thermal stability and separation of the catalyst make it a good heterogeneous system and a useful alternative to other heterogeneous catalysts. Also, the catalyst could be magnetically separated and reused six times without significant loss of catalytic activity. Copyright

Cu-MCM-41 nanoparticles: An efficient catalyst for the synthesis of 5-substituted 1H-tetrazoles via [3+2] cycloaddition reaction of nitriles and sodium azide

[3 + 2] cycloaddition reaction of various types of nitriles and sodium azide (NaN 3) were studied in the presence of nano-sized Cu-MCM-41 as an efficient recoverable heterogeneous catalyst. Nano-sized Cu-MCM-41 mesoporous molecular sieves with various Si/Cu molar ratios were synthesized by direct insertion of metal ions at room temperature. The textural properties of the materials have been studied by means of XRD, FTIR, SEM and TEM techniques. Catalytic behavior of Cu-MCM-41 was also investigated by pyridine absorption and potentiometric titration. The reactions data verified characterization results and show that Cu-MCM-41 with Si/Cu molar ratio of 20 has considerably better catalytic activity compared to the other molar ratios. To investigate reusability, the catalyst was recovered by simple filtration and reused for several cycles with consistent activity.

Nano TiO2/SO42- as a heterogeneous solid acid catalyst for the synthesis of 5-substited-1 H-tetrazoles

An efficient and economical protocol for the synthesis of 5-substituted-1H-tetrazoles from various nitriles and sodium azide is reported using nano TiO2/SO42+ as an effective heterogeneous catalyst.A wide variety of aryl nitriles underwent [3 + 2] cycloaddition to afford tetrazoles in good to excellent yields.

Heteropolyacid catalyzed click synthesis of 5-substituted 1H-tetrazoles from [bmim]N3 and nitriles under solvent-free conditions

A simple and solvent-free route for the synthesis of 5-substituted 1H-tetrazoles is reported. In this method, 5-substituted 1H-tetrazoles are synthesized from nitriles and [bmim]N3 with heteropolyacid (H 3PW12O40/sub

Highly efficient synthesis of 1- and 5-substituted 1H-tetrazoles using chitosan derived magnetic ionic liquid as a recyclable biopolymer-supported catalyst

A general method for the efficient synthesis of 1- and 5-substituted 1H-tetrazoles from nitriles and amines is described using chitosan supported magnetic ionic liquid nanoparticles (CSMIL) as a novel heterogeneous catalyst. The application of this catalyst allows the synthesis of a variety of tetrazoles in high yields at low temperature. This new magnetic catalyst has been prepared from chitosan (the most abundant biopolymer in nature and cheap industrial waste) and methyl imidazole (a widely available backbone of ionic liquids) which was reacted with FeCl3 to obtain the CS-EMImFeCl4 catalyst. This methodology illustrates a very simple procedure, with wide applicability, environmental friendliness and reusability of catalyst. The new catalyst was characterized using some different microscopic and spectroscopic techniques such as transmission electron microscopy (TEM), scanning electron microscopy (SEM), FTIR spectroscopy, and Raman spectroscopy. The novel catalyst has therefore a great potential to be used in green processes. The Royal Society of Chemistry 2013.

Facile synthesis of 5-substituted-1H-tetrazoles and 1-substituted-1H- tetrazoles catalyzed by recyclable 4′-phenyl-2,2′:6′,2″- terpyridine copper(II) complex immobilized onto activated multi-walled carbon nanotubes

5-Substituted-1H-tetrazoles can conveniently be synthesized from the corresponding nitriles by reaction with NaN3 using the efficient and recyclable heterogeneous catalyst prepared by immobilization of copper(II) complex of 4′-phenyl-2,2′:6′,2″-terpyridine on activated multi-walled carbon nanotubes [AMWCNTs-O-Cu(II)-PhTPY]. Excellent results were obtained in each case affording the corresponding tetrazole adducts in good to excellent yields. In general, aromatic nitriles with electron-donating group could be accomplished as well as that with electron-withdrawing groups. By leaving out nitrile from the reaction and adding CH(OEt)3 and amines bearing various substituents, 1-substituted-1H-tetrazoles formed in water in high yields. The reported protocols have the advantages of rapid assembly of a host of heterocyclic systems in high yields with the added advantage of recycling and reuse of the catalyst.

Zeolite and sulfated zirconia as catalysts for the synthesis of 5-substituted 1H-tetrazoles via [2+3] cycloaddition of nitriles and sodium azide

The [2+3] cycloaddition between various nitriles and sodium azide proceeds smoothly in the presence of zeolite and sulfated zirconia as effective catalysts, in water and DMF/MeOH, to give the corresponding 5-substituted 1H-tetrazoles in good to high yields. The reaction most probably proceeds through the in situ formation of catalyst azide species, followed by a successive [2+3] cycloaddition with the nitriles. This method has the advantages of high yields, simple methodology and easy work-up. The catalyst can be recovered by simple filtration and reused with good yields.