21871-44-3

Basic information

• Product Name: 5-(3-NITROPHENYL)-2H-TETRAZOLE
• Synonyms: 5-(3-NITROPHENYL)-2H-TETRAZOLE;5-(3-NITROPHENYL)-1H-TETRAZOLE;BUTTPARK 32\02-06
• CAS NO: 21871-44-3
• Molecular Formula: C₇H₅N₅O₂
• Molecular Weight: 191.15
• Mol File: 21871-44-3.mol

Chemical Properties

• Boiling Point: 424.6 °C at 760 mmHg
• Flash Point: 210.6 °C
• Appearance: /
• Density: 1.534 g/cm³
• Vapor Pressure: 2.05E-07mmHg at 25°C
• Refractive Index: 1.662
• CAS DataBase Reference: 5-(3-NITROPHENYL)-2H-TETRAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(3-NITROPHENYL)-2H-TETRAZOLE(21871-44-3)
• EPA Substance Registry System: 5-(3-NITROPHENYL)-2H-TETRAZOLE(21871-44-3)

Safety Data

• Hazardous Substances Data: 21871-44-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-(3-NITROPHENYL)-2H-TETRAZOLE is used as a building block for the synthesis of pharmaceutical compounds due to its diverse biological activities and potential applications in drug development.
Used in Antihypertensive Applications:
5-(3-NITROPHENYL)-2H-TETRAZOLE is used as a potential antihypertensive agent, indicating its possible use in the development of medications for the treatment of high blood pressure.
Used in Antifungal and Antibacterial Applications:
5-(3-NITROPHENYL)-2H-TETRAZOLE has been investigated for its antifungal and antibacterial properties, suggesting its potential use in the development of treatments for fungal and bacterial infections.
Used in Organic Synthesis:
The nitrophenyl group in 5-(3-NITROPHENYL)-2H-TETRAZOLE contributes to its ability to undergo redox reactions, making it a versatile reagent in organic synthesis for the development of various chemical compounds.

InChI:InChI=1/C7H5N5O2/c13-12(14)6-3-1-2-5(4-6)7-8-10-11-9-7/h1-4H,(H,8,9,10,11)

Upstream product

• 619-24-9 3-nitrobenzonitrile 
• 99-61-6 3-nitro-benzaldehyde 
• 100-47-0 benzonitrile 
• 18039-42-4 5-phenyl-2H-1,2,3,4-tetrazole 
• 13331-27-6 m-nitrobenzene boronic acid 
• 99-08-1 1-methyl-3-nitrobenzene 
• 619-25-0 3-Nitrobenzyl alcohol 
• 585-79-5 m-nitrobromobenzene 
• 3431-62-7 3-nitrobenzaldoxime 
• 18039-42-4 5-Phenyl-1H-tetrazole 

Downstream Products

• 73732-51-1 5-(3-aminophenyl)-1H-tetrazole 
• 107933-55-1 5-(3-Nitro-phenyl)-2-vinyl-2H-tetrazole 
• 122733-39-5 2-methyl-5-(3-nitrophenyl)-1,3,4-oxadiazole 
• 73732-51-1 5-(3-aminophenyl)-2H-tetrazole 
• 69790-73-4 2-Methyl-5-(3-nitrophenyl)-2H-tetrazole 
• 1448724-40-0 2-benzyl-4-chloro-7-(2-methyl-2H-tetrazol-5-yl)-9H-pyrimido[4,5-b]indole 
• 114934-51-9 3-(2H-2-Methyltetrazol-5-yl)benzenamine 

Relevant articles and documents

Synthesis and characterization of magnetic Fe3O4@Creatinine@Zr nanoparticles as novel catalyst for the synthesis of 5-substituted 1H-tetrazoles in water and the selective oxidation of sulfides with classical and ultrasonic methods

Tetrazoles and sulfoxide compounds have a wide range of applications in industries and are of great expectation to be environmentally friendly and cost-effective. This paper reports the introduction of zirconium supported on Fe3O4 na

Anti-tumor metastasis effect of 2, 4, 7-trisubstituted pyrimidino indole compound

The invention relates to a compound with a 2, 4, 7-trisubstituted pyrimidino indole structure. The compound can inhibit tumor cell migration and invasion at a very low concentration, and has an effect superior to that of a clinically common drug cis-platinum. In addition, the compound can also inhibit the expression of matrix metalloproteinase related protein which plays an important role in tumor migration and invasion processes. The invention also relates to a preparation method of the compound and application of the compound in marking, diagnosis, prevention and treatment or adjuvant therapy of tumors.

Antitumor effect of 2, 4, 7-trisubstituted pyrimidino indole compound

The invention relates to a series of compounds with 2, 4, 7-trisubstituted pyrimidino indole structures, and the compounds can inhibit the growth of various tumor cells, and particularly, the compounds can efficiently inhibit the proliferation of breast cancer, cervical cancer, gastric adenocarcinoma and liver cancer cells. In addition, the compound can inhibit tumor cell clone formation at a very low concentration and promote tumor cell apoptosis. The invention also relates to a preparation method of the compound and application of the compound in marking, diagnosis, prevention and treatment or adjuvant therapy of tumors.

2, 4, 7 -substituted pyrimido indole compound antitumor drug resistance effect

The invention relates to 2, 4 and 7 - tri-substituted pyrimido-indole structural compounds which can inhibit the growth of various drug-resistant tumor cells, and in particular, can efficiently inhibit doxorubicin resistant breast cancer. Cisplatin-resistant lung cancer and cisplatin liver cancer cell proliferation. In addition, the compounds of the present invention can inhibit the formation of drug-resistant tumor cell clones at very low concentrations and inhibit P glycoprotein and ABCG2 transport in vitro functions. The invention also relates to a preparation method of the compound and an application of the compound in tumor treatment or adjuvant therapy.

Catalytic conversion of 2,4,5-trisubstituted imidazole and 5-substituted 1H-tetrazole derivatives using a new series of half-sandwich (η6-p-cymene)Ruthenium(II) complexes with thiophene-2-carboxylic acid hydrazone ligands

A new series of half-sandwich (η6-p-cymene) ruthenium(II) complexes with thiophene-2-carboxylic acid hydrazide derivatives [Ru(η6-p-cymene)(Cl)(L)] [L = N'-(naphthalen-1-ylmethylene)thiophene-2-carbohydrazide (L1), N'-(anthracen-9-ylmethylene)thiophene-2-carbohydrazide (L2) and N'-(pyren-1-ylmethylene)thiophene-2-carbohydrazide (L3)] were synthesized. The ligand precursors and their Ru(II) complexes (1–3) were structurally characterized by spectral (IR, UV–Vis, NMR and mass spectrometry) and elemental analysis. The molecular structures of the ruthenium(II) complexes 1–3 were determined by single-crystal X-ray diffraction. All complexes were used as catalysts for the one-pot three-component syntheses of 2,4,5-trisubstitued imidazole and 5-substituted 1H-tetrazole derivatives. The catalytic studies optimized parameters as solvent, temperature and catalyst. The catalysts revealed very active for a broad range of aromatic aldehydes presenting either electron attractor or electron donor substituents and, although less active, moderate to high activities were observed for alkyl aldehydes.

Cu attached functionalized mesoporous MCM-41: a novel heterogeneous nanocatalyst for eco-friendly one-step thioether formation reaction and synthesis of 5-substituted 1H-tetrazoles

In the current study, a mesoporous copper-attached functionalized MCM-41 with the DL-Pyroglutamic acid framework has been produced through a post-synthetic method. The MCM-41 functionalization technique has been used to synthesize this novel heterogeneous catalyst. The material has been identified fully using XRD, FT-IR, BET, EDX, elemental mapping, SEM, and TGA. This catalyst displays high catalytic performance in the one-step thioether formation (C–S) reaction and synthesis of 5-substituted 1H-tetrazoles. The main aspects of this economical copper-catalyzed procedure are green synthesis, slighter experimental conditions, and less reaction time with no additives. Further benefits comprise experimental comfort of handling, secure replacement to dangerous, damaging, and poisoning regular Lewis’s acid catalysts, and reusability with constant catalytic performance. Graphic abstract: [Figure not available: see fulltext.]

Sustainable and recyclable magnetic nanocatalyst of 1,10-phenanthroline Pd(0) complex in green synthesis of biaryls and tetrazoles using arylboronic acids as versatile substrates

A magnetic nanocatalyst was purveyed as a heterogeneous recoverable palladium-based catalyst anchored on green, sustainable and phosphine free support. Resulted Fe3O4@SiO2-Phen-Pd(0) nanocatalyst bearing powerful phenanthroline ligand was thoroughly characterized by physicochemical approaches like UV–vis, FT-IR, EDX, XRD, TGA, ICP, VSM, DLS, FESEM, and TEM analyses. After finding trustable data, the obtained magnetic catalyst was considered to be applied in the Suzuki-Miyaura type C-C couplings and getting corresponding tetrazoles using arylboronic acid derivatives as alternate precursors of aromatic halides and stupendous data were observed.

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.

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.]

Fe3O4@L-lysine-Pd(0) organic–inorganic hybrid: As a novel heterogeneous magnetic nanocatalyst for chemo and homoselective [2 + 3] cycloaddition synthesis of 5-substituted 1H-tetrazoles

An efficient and sustainable synthetic protocol has been presented to synthesis and 5-substituted 1H-tetrazole privileged heterocyclic substructures. The synthetic protocol involves two-component reaction between aryl nitriles and NaN3 in water using complex of L-lysine-palladium nanoparticles (NPs) modified Fe3O4 nanoparticles as magnetically separable, recyclable, and reusable heterogeneous catalyst. Magnetically retrievable L-lysine-Pd(0) modified Fe3O4 nanoparticles were applied in [2 + 3] cycloaddition synthesis of 5-substituted 1H-tetrazoles. The advantages of this strategy include easy recovery and efficient reusability of the expensive Pd NPs, obtaining high yields of [2 + 3] cycloaddition, short reaction times, and all of the reported synthetic strategies are being performed in water as green solvent for a wide range of substrates.