313535-27-2

Usage

Chemical Class

Tetrazole derivatives

Common Uses

Reagent in organic synthesis and pharmaceutical research

Thermal Stability

High

Explosive Properties

Yes

Industrial Applications

Energetic materials and propellants

Use as Precursor

Synthesis of various pharmaceuticals and agrochemicals

Potential Applications

Development of new materials and as a building block in the synthesis of organic compounds.

Upstream product

• 134-32-7 1-amino-naphthalene 
• 122-51-0 orthoformic acid triethyl ester 
• 129354-22-9 1-naphthylthioformamide 
• 6330-51-4 1-naphthylformamide 

Downstream Products

• 634-42-4 N-1-naphthalenyl-benzamide 
• 33555-17-8 2-phenyl-1H-benzo[g]indole 
• 1449517-03-6 C₁₉H₁₃BrN₂ 

Relevant academic research and scientific papers

Practical synthesis of tetrazoles from amides and phosphorazidates in the presence of aromatic bases

Tetrazoles were effectively synthesized from amides using diphenyl phosphorazidate or bis(p-nitrophenyl) phosphorazidate in the presence of aromatic bases. Various amides underwent the proposed cycloaddition reaction to provide the corresponding tetrazoles. Studies on the racemization of chiral substrates were also performed. Overall, the proposed synthesis method enables the preparation of 1,5-disubstituted and 1-substituted tetrazoles, and 5-substituted 1H-tetrazoles without using toxic or explosive reagents.

Fe3O4?Hydrotalcite-NH2-CoII NPs: A novel and extremely effective heterogeneous magnetic nanocatalyst for synthesis of the 1-substituted 1H-1, 2, 3, 4-tetrazoles

In this study, we present a versatile and easy procedure for modifying a ferrite nanoparticles so step by step. A new nanocatalyst was prepared via CoII immobilized onto an aminated ferrite nanoparticles (Fe3O4?HT?AEPH2-CoII). The catalyst was fully characterized by FT-IR, EDX, FE-SEM, TGA, XRD, and VSM analyses. In the preparation of 1-substituted-1-H-tetrazole, the corresponding nanocatalyst shown great catalytic activity. The reaction contains expeditious reusable catalyst (Fe3O4?AEPH2-CoII) that promotes condensation between sodium azide, triethyl ortho-formate, and diversity of heterocyclic/aromatic amines. Also, an environmentally toxic solvent was eliminated. A significant improvement in the synthetic efficacy (95%, yield) was obtained by this new sustainable and eco-friendly protocol as well as high purity. The current procedure as a green protocol offers benefits including a simple operational procedure, an excellent yield of products, mild reaction conditions, minimum chemical wastes, short reaction time, and easy catalyst synthesis. Without any significant reduction in the catalytic performance, up to four recyclability cycles of the catalyst were obtained. The optimization results suggest that the best condition in the preparation of tetrazole derivatives is 0.005 g of the Fe3O4?HT?AEPH2-CoII catalyst where H2O is the solvent at 90 °C. The proposed protocol could be applied on a wider scope of the substrate (i.e., electron-deficient and electron-rich).

Green synthesis of the 1-substituted 1H-1, 2, 3, 4-tetrazoles over bifunctional catalyst based on copper intercalated into Mg/Al hydrotalcite modified magnetite nanoparticles

An effective one-pot, convenient process for the synthesis of 1- substituted 1H-tetrazoles from triethyl orthoformate, amines, and sodium azide is described using copper (II) doped and immobilized on functionalized magnetic hydrotalcite (Fe3O4/HT-NH2 CuII) as a novel recyclable catalyst. The application of this catalyst allows the synthesis of a variety of tetrazoles in good to excellent yields in water. The new catalyst was characterized using Fourier transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD), scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX), thermogravimetric analysis (TGA), vibration sample magnetometry (VSM) and inductively coupled plasma analysis (ICP-OES). This new procedure offers several advantages such as short operational simplicity, practicability, and applicability to various substrates and the absence of any tedious workup or purification. The loading amount of CuII (doped and immobilized) on functionalized magnetic hydrotalcite was indicated to be 4.66 mmol g?1, obtained from the ICP-OES analysis. Also, the excellent catalytic performance, thermal stability, and separation of the catalyst make it an excellent 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.

SiO2-H3BO3 promoted solvent-free, green and sustainable synthesis of bioactive 1-substituted-1H-tetrazole analogues

In the present study, a focused library of multi functionalized 1-substituted-1H-tetrazole analogues 4(a-o) were synthesized, which were typically accessed via a facile, solvent-free and green synthetic protocol. The reaction involves expeditious reusable catalyst (SiO2-H3BO3) promoted condensation between a variety of heterocyclic/aromatic amines, sodium azide and triethyl ortho-formate, eliminating the use of an environmentally toxic solvent. This new eco-friendly and sustainable protocol resulted in a remarkable enhancement in the synthetic efficiency (90-97%, yield) with high purity. This silica-boric acid catalyst is air and water stable and easy to prepare from cheap silica and boric acid. The present methodology is a green protocol offering several advantages such as an excellent yield of products, a simple operational procedure, minimizing production of chemical wastes, mild reaction conditions, a shorter reaction profile, easy preparation of the catalyst and its recyclability up to five cycles without any appreciable loss in catalytic activity. The optimization conditions achieved in the present study revealed that 2.5 mol% of the SiO2-H3BO3 catalyst under solvent-free conditions at 90 °C are the best suited conditions for the synthesis of tetrazole derivatives in excellent yields. The present protocol is applicable to a broader substrate scope (electron-rich and electron-deficient). Compounds possessing a nicotinic acid nucleus (4e, 4f, 4g) displayed strongest inhibition against AChE with IC50 values of 0.43 μM, 0.21 μM and 0.26 μM, respectively. The results revealed that the electronic effect of substituents inflicts a prominent effect on AChE activity. This journal is

Ultrasound-promoted one-pot three component synthesis of tetrazoles catalyzed by zinc sulfide nanoparticles as a recyclable heterogeneous catalyst

Ultrasound irradiation was applied for the appropriate and rapid synthesis of 1-substituted tetrazoles through cyclization reaction of various primary amines, sodium azide and triethyl orthoformate. This reaction was effectively catalyzed by ZnS nanoparti

Sulfonic acid-functionalized silica-coated magnetic nanoparticles as an efficient reusable catalyst for the synthesis of 1-substituted 1H-tetrazoles under solvent-free conditions

Regarding green chemistry goals, silica-coated magnetite nanoparticles open up a new avenue to introduce a very useful and efficient system for facilitating catalyst recovery in different organic reactions. Therefore, in this paper the preparation of sulf

Efficient uncatalyzed conversion of primary and secondary thioamides into 1-substituted, 5-substituted, 1, 5-disubstituted and annulated tetrazoles

Unprecedented high-yield simple and mild conversion of primary aliphatic and aromatic thioamides into 5-substituted tetrazoles on treatment with a combination of tetrachlorosilane and sodium azide in refluxing acetonitrile has been achieved. Secondary acyclic, cyclic, and heterocyclic thioamides could also be transformed in high yields into 1-substituted, 1,5-disubstituted, or annulated tetrazoles under the same reaction condition. Copyright Taylor & Francis Group, LLC.

Synthesis of new functionally substituted 1-R-tetrazoles and their 5-amino derivatives

It has been shown that amino derivatives of sulfanilamide, and also some functionally substituted primary arylamines and cycloalkylamines, undergo heterocyclization with triethyl orthoformate and sodium azide with the formation of 1-monosubstituted tetraz