171018-19-2

Basic information

• Product Name: Pyridine, 2-(1H-tetrazol-1-yl)- (9CI)
• Synonyms: Pyridine, 2-(1H-tetrazol-1-yl)- (9CI)
• CAS NO: 171018-19-2
• Molecular Formula: C6H5N5
• Molecular Weight: 147.1374
• Product Categories: PYRIDINE
• Mol File: 171018-19-2.mol

Chemical Properties

• Melting Point: 125-126.5 °C(Solv: ethanol (64-17-5))
• Boiling Point: 329.3±34.0 °C(Predicted)
• Appearance: /
• Density: 1.44±0.1 g/cm3(Predicted)
• PKA: 0.05±0.10(Predicted)
• CAS DataBase Reference: Pyridine, 2-(1H-tetrazol-1-yl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridine, 2-(1H-tetrazol-1-yl)- (9CI)(171018-19-2)
• EPA Substance Registry System: Pyridine, 2-(1H-tetrazol-1-yl)- (9CI)(171018-19-2)

Safety Data

• Hazardous Substances Data: 171018-19-2(Hazardous Substances Data)

Upstream product

• 504-29-0 2-aminopyridine 
• 149-73-5 trimethyl orthoformate 
• 15009-91-3 2-nitropyridine 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 4589-12-2 N-(pyrid-2-yl)benzamide 

Relevant articles and documents

First examples of Co(II), Ni(II), and Cu(II) coordination compounds with 1-(pyrid-2-yl)-1H-tetrazole: Synthesis, structure and properties

Coordination compounds of cobalt(II), nickel(II), and copper(II) with a poly nitrogen-containing heterocyclic ligand 1-(pyrid-2-yl)-1H-tetrazole (1-Pytz) such as [Cu(1-Pytz)2Cl2]n, [M(1-Pytz)2(H2O)Cl2] (M = Co, Ni), [M(1-Pytz)2(C2N3)2]n (M = Co, Ni) have been synthesized. The compounds have been studied by means of infrared diffuse reflectance spectroscopy, single-crystal and powder X-ray diffraction, and static magnetic susceptibility. The studies on the μeff(T) for the [Cu(1-Pytz)2Cl2]n, [Co(1-Pytz)2(C2N3)2]n and [Ni(1-Pytz)2(C2N3)2]n polynuclear complexes in the temperature range of 2–300 K have shown that exchange interactions between spins of metal ions are weak.

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

Efficient and rapid synthesis of 1-substituted-1H-1,2,3,4-tetrazoles in the acidic ionic liquid 1-n-butylimidazolium tetrafluoroborate

An efficient synthesis leading directly to 1-substituted-1H-1,2,3,4-tetrazoles from easily available amines and sodium azide in stoichiometric proportions using a room-temperature ionic liquid, namely, 1-n-butylimidazolium tetrafluoroborate in excellent yields is described. The inherent Br?nsted acidity and high polarity of the IL results in a significant enhancement in the reaction rate.

Synthesis and characterisation of tetrazole compounds: 3 Series of new ligands representing versatile building blocks for iron(II) spin-crossover compounds

New tetrazole compounds were synthesized and characterised by NMR and FTIR spectroscopy as well as by single crystal X-ray diffraction. We present in this paper mono- and ditetrazoles, which represent a versatile class of building blocks for the formation of mononuclear iron(II) complexes with monotetrazoles as terminal ligands as well as iron(II) coordination polymers with ditetrazoles as bridging ligands. Especially, the series of α,ω-bis[tetrazol-1- yl]-alkanes open the field of fascinating supramolecular structures with spin transition properties.

Oxidation/ MCR domino protocol for direct transformation of methyl benzene, alcohol, and nitro compounds to the corresponding tetrazole using a three-functional redox catalytic system bearing TEMPO/Co(III)-porphyrin/ Ni(II) complex

A redox catalytic system for oxidation-reduction reactions and the domino preparation of tetrazole compounds from nitro and alcohol precursors was designed, prepared and characterized by UV–vis, GPC, TGA, XRD, EDX, XPS, VSM, FE-SEM, TEM, DLS, BET, NMR, and ICP analyses. The catalyst was prepared via several successive steps by demetalation of chlorophyll b, copolymerization with acrylated TEMPO monomers, complexation with Ni and Co metals (In two different steps), then immobilized on magnetic nanoparticles. The presence of three functional groups including TEMPO, coordinated cobalt, and coordinated nickel in the catalyst, allowed the oxidation of various types of alcohols, alkyl benzenes as well as the reduction of nitro compounds by a single catalyst. All reactions yielded up to 97 % selectivity for oxidation and reduction reactions. Next, the ability of the catalyst to successfully convert alcohol, methyl benzenes and nitro to their corresponding tetrazoles was studied.

Efficient reduction of nitro compounds and domino preparation of 1-substituted-1H-1,2,3,4-tetrazoles by Pd(ii)-polysalophen coated magnetite NPs as a robust versatile nanocomposite

A new, versatile, and green methodology has been developed for the efficient NaBH4-reduction of nitroarenes as well as the domino/reduction MCR preparation of 1-substituted-1H-1,2,3,4-tetrazoles using Pd(ii)-polysalophen coated magnetite NPs as an efficient heterogeneous magnetically recyclable nanocatalyst. Polysalophen was firstly prepared based on a triazine framework with a high degree of polymerization, then coordinated to Pd ions and, finally, the resulting hybrid was immobilized on magnetite NPs. The catalyst was characterized by various instrumental and analytical methods, including GPC, DLS, N2adsorption-desorption, TGA, VSM, TEM, HRTEM, EDX, XPS, XRD, and ICP analyses. The catalyst possesses dual-functionality including the reduction of nitroarenes and the construction of tetrazole rings all in one stepviaa domino protocol. High to excellent yields were obtained for both nitro reduction and the direct preparation of 1-substituted-1H-1,2,3,4-tetrazoles from nitro compounds. Insight into the mechanism was conducted by XPSin situas well as DLSin situalong with several control experiments. Recyclability of the catalyst was studied for 6 consecutive runs along with metal leaching measurements in each cycle.

2-aminoethanesulfonic acid immobilized on epichlorohydrin functionalized Fe3O4@WO3 (Fe3O4@WO3-EAE-SO3H): A novel magnetically recyclable heterogeneous nanocatalyst for the green one-pot synthesis of 1-substituted-1H-1, 2, 3, 4-tetrazoles in water

In this research 2-aminoethanesulfonic acid immobilized on epichlorohydrin functionalized Fe3O4@WO3 (Fe3O4@WO3- EAE-SO3H) has been introduced as a novel and efficient magnetic nanocatalyst for appropriate and rapid synthesis of 1-substituted-1H-1, 2, 3, 4-tetrazoles. This new nanocatalyst was then characterized using FT-IR, XRD, TEM, EDS, TGA, FE-SEM, CHNS and VSM techniques. The above experimental results allowed determination of the composition of Fe3O4@WO3-EAE-SO3H and clearly revealed that the nanoparticles are spherical in shape with particle size in the range of 723nm and superparamagnetic behavior. Fe3O4@WO3- EAE-SO3H as an excellent replacement for Br?nsted acids was shown to be highly efficient in the rapid preparation of 1- substituted-1H-1, 2, 3, 4-tetrazoles through the cyclization reaction of various primary amines, triethyl orthoformate and 1- butyl-3-methylimidazolium azide ([bmim][N3]). Compared with conventional methods, the present protocol has considerable advantages such as short reaction time, mild reaction conditions, easy work-up, pure products with high yields, catalyst recovery using an external magnet and reuse of the catalyst several times without noticeable deterioration in catalytic activity. In addition to the aforementioned favourable properties, the remarkable feature of the present protocol is the use of water as environmentally benign solvent, which eliminates the use of toxic solvent.

Synthetic manifestation of nitro substituted tetrazole-N-(hetero)aryl derivatives and energetic studies

A workable cost-efficient synthetic method for the construction of nitro substituted tetrazole-N-aryl/heteroaryl derivatives is discussed here. The energetic functional groups-NO2,-NHNO2 and-N3 are reliably inserted into the molecular backbone, making the tetrazole-N-aryl derivatives highly energetic and insensitive to heat and impact. For example, the tetrazole derivatives 7 and 8, bearing a-NO2 or a-NHNO2 group, exhibit energetic properties close to RDX, but with enhanced insensitivity. Most of the synthesized compounds show exothermic decomposition and are consequently useful for energetic material applications.

Trifluoromethanesulfonimide catalysed synthesis of 1-substituted-1H-1,2,3,4-tetrazoles using glycerol as green solvent at room temperature

A direct synthetic protocol is developed for the synthesis of 1-substituted-1H-1,2,3,4-tetrazoles via a three-component condensation of primary amines, triethyl orthoformate and sodium azide in the presence of 5 mol% of trifluoromethanesulfonimide (HNTf2) in glycerol at room temperature with good to excellent yields.

HClO4-SiO2 as an efficient and reusable heterogeneous catalyst for the synthesis of 1-substituted tetrazoles

An efficient and direct protocol is described for the preparation of 1-substituted 1H-1,2,3,4-tetrazoles by the reaction of primary amines, triethyl orthoformate and sodium azide in the presence of catalytic amount of silica-supported perchloric acid under solvent-free and heterogeneous conditions. The thermal solvent-free green procedure offers advantages such as simple methodology, easy work-up, high yield, recovery and reusability of catalyst.