73096-43-2

Basic information

• Product Name: 5,5’-(1,2-phenylene)bis(1H-tetrazole)
• Synonyms: 5,5’-(1,2-phenylene)bis(1H-tetrazole)
• CAS NO: 73096-43-2
• Molecular Weight: 214.189
• Mol File: 73096-43-2.mol

Chemical Properties

• CAS DataBase Reference: 5,5’-(1,2-phenylene)bis(1H-tetrazole)(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5’-(1,2-phenylene)bis(1H-tetrazole)(73096-43-2)
• EPA Substance Registry System: 5,5’-(1,2-phenylene)bis(1H-tetrazole)(73096-43-2)

Safety Data

• Hazardous Substances Data: 73096-43-2(Hazardous Substances Data)

Upstream product

• 91-15-6 phthalonitrile 
• 176636-06-9 2,2'-bis(tributylstannyl)-5,5'-o-phenylenebis(tetrazole) 

Relevant articles and documents

Preparation of 5-substituted 1H-tetrazoles from nitriles in water

The addition of sodium azide to nitriles to give 1H-tetrazoles is shown to proceed readily in water with zinc salts as catalysts. The scope of the reaction is quite broad; a variety of aromatic nitriles, activated and unactivated alkyl nitriles, substituted vinyl nitriles, thiocyanates, and cyanamides have all been shown to be viable substrates for this reaction.

A magnetically retrievable heterogeneous copper nanocatalyst for the synthesis of 5-substituted tetrazoles and oxidation reactions

Abstract: A copper complex anchored on functionalized Fe3O4 nanoparticles was prepared by a simple and inexpensive procedure using commercially available materials. The prepared catalyst was characterized by a range of physical and spectroscopic techniques. Ease of operation, high efficiency, eco-friendly procedure, easy separation of the catalyst and reusability for several consecutive runs without significant loss of its activity are several advantages of this catalyst. The catalytic activity has been explored for the oxidation of sulfides, oxidative coupling of thiols and synthesis of 5-substituted tetrazoles. Graphical Abstract: A magnetically retrievable heterogeneous copper nanocatalyst for the synthesis of 5-substituted tetrazoles and oxidation reactions[Figure not available: see fulltext.].

Mechanism of the zinc-catalyzed addition of azide ion to unsaturated compounds: Synthesis of 5-substituted 1Н-tetrazoles from nitriles and of 1-substituted 1Н-tetrazole-5-thiols from isothiocyanates

The mechanism of the formation of 5-substituted 1H-tetrazoles from organic nitriles and thiocyanates in the presence of NaN3 and ZnCl2 in aliphatic alcohols was studied. The results of this study allowed efficient methods of synthesis of substituted tetrazoles from nitriles, thiocyanates, and isothiocyanates to be proposed.

An improved protocol for the preparation of 5-substituted tetrazoles from organic thiocyanates and nitriles

Organic thiocyanates and nitriles are converted efficiently into the corresponding 5-substituted 1H-tetrazoles by treatment with zinc(II) chloride and sodium azide in aliphatic alcohols. The presented procedure provides mild reaction conditions, short reaction times, and good to excellent yields for a wide range of substrates, including deactivated aliphatic nitriles and thermally unstable thiocyanates. Georg Thieme Verlag Stuttgart · New York.

Copper iodide nanoparticles-catalysed cyanation of aryl halides using non-toxic K4[Fe(CN)6] in the presence of 1,2-bis(5-tetrazolyl)benzene as an efficient ligand

Cyanation of aryl bromides were carried out with K4[Fe(CN) 6] in the presence of catalytic amounts of a copper salt and 1,2-bis(5-tetrazolyl)benzene as a ligand under thermal conditions. This method has the advantages of high yields, simple methodology and easy work up.

Efficient transformation of inactive nitriles into 5-substituted 1 H-tetrazoles using microwave irradiation and their applications

Efficient transformations of inactive nitriles into 5-substituted 1H-tetrazoles in DMF in a microwave reactor are described. The present method is applied to the synthesis of tetrazolato-bridged dinuclear platinum(II) complex and tetrazole C1-ribonucleoside phosphoramidite. Georg Thieme Verlag Stuttgart, New York.

Click chemistry for the synthesis of 5-substituted 1H-tetrazoles from boron-azides and nitriles

A novel and metal free catalysis of synthesizing 5-substituted 1H-tetrazoles through 1,3-dipolar cycloaddition of boron-azides and nitriles is reported with broad substrate scope and excellent yields.

Highly efficient synthesis of 5-substituted 1H-tetrazoles catalyzed by Cu-Zn alloy nanopowder, conversion into 1,5- and 2,5-disubstituted tetrazoles, and synthesis and NMR studies of new tetrazolium ionic liquids

A series of 5-substituted 1H-tetrazoles were synthesized through [3+2] cycloaddition reactions between nitriles RCN and NaN3 in the presence of Cu-Zn alloy nanopowder as catalyst. The 1,5-dibutyl, 1-butyl-5-hexyl, 2,5-dibutyl, and 2-butyl-5-hexyl derivatives were then used as building blocks to synthesize several novel tetrazolium ionic liquids (ILs) with EtSO 4-, OTf-, and NTf2- counterions. Whereas alkylation of the 2,5-dialkyltetrazoles selectively gave the N-4 alkylated onium salts, with the 1,5-dialkyl derivatives approximately 1:1 mixtures of two tetrazolium salts were formed by alkylation at N-3 and N-4. The triflate and ethyl sulfate salts are room-temperature ILs that are hydrophilic, whereas the NTf2 salts are low-melting ILs and are hydrophobic. The resulting tetrazolium-based ionic liquids were studied by various multinuclear and 2D NMR techniques including natural abundance 15N and 1H/15N correlations.

Amine salt-catalyzed synthesis of 5-substituted 1H-tetrazoles from nitriles

The [3+2] cycloaddition reaction between sodium azide and various organic nitriles proceeds smoothly in the presence of amine salts as catalyst in dimethylformamide. The corresponding 5-substituted 1-H tetrazoles were obtained under mild condition in good to excellent yields. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Taylor & Francis Group, LLC.

Practical synthesis of 5-substituted tetrazoles under microwave irradiation

5-Substituted tetrazoles were prepared by treatment of nitriles with sodium azide and triethylammonium chloride in nitrobenzene in a microwave reactor. This practical method combines the advantages of previous procedures, including good-to-excellent yields, short reaction times, and easy isolation of the product. Moreover, sterically hindered tetrazoles, as well as those deactivated by electron-donating groups, can be prepared. Georg Thieme Verlag Stuttgart.