74815-22-8

Usage

General Description

The chemical 4-(1H-tetrazol-5-yl)benzaldehyde is a compound that consists of a benzene ring with a tetrazole ring attached to it at the 4-position, as well as an aldehyde functional group at the 1-position. It is commonly used in organic synthesis and pharmaceutical research, particularly in the development of pharmaceutical drugs. The tetrazole ring provides unique properties to the compound, including its ability to act as a bioisostere for carboxylic acid groups in drug design. This makes 4-(1H-tetrazol-5-yl)benzaldehyde a valuable building block for the synthesis of diverse pharmaceutical compounds. Additionally, the aldehyde functional group can undergo various chemical reactions, further expanding the potential applications of 4-(1H-TETRAZOL-5-YL)BENZALDEHYDE in organic chemistry.

Upstream product

• 105-07-7 4-cyanobenzaldehyde 
• 4897-84-1 Methyl 4-bromobutyrate 
• 501126-02-9 C₈H₈N₄O 
• 623-27-8 terephthalaldehyde, 
• 87199-17-5 4-formylphenylboronic acid, 
• 67-68-5 dimethyl sulfoxide 
• 539-74-2 Ethyl 3-bromopropionate 
• 1122-91-4 4-bromo-benzaldehyde 
• 179942-55-3 (4-(1H-tetrazol-5-yl)phenyl)boronic acid 
• 298-12-4 Glyoxilic acid 

Downstream Products

• 198904-64-2 4-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-benzaldehyde 
• 1333480-81-1 (5Z)-5-[4-(1H-tetrazol-5-yl)benzylidene]imidazolidine-2,4-dione 
• 1401235-37-7 (Z)-5-(4-(1H-tetrazol-5-yl)benzylidene)-4-thioxothiazolidin-2-one 

Relevant academic research and scientific papers

Microwave Assisted Synthesis of 5-[4-(3-Phenyl-4,5-dihydro-1H-pyrazol-5-yl)phenyl]-1H-tetrazole Derivatives and Their Antimicrobial Activity

In the present study, we report the synthesis of 5-[4-(3-phenyl-4,5-dihydro-1H-pyrazol-5-yl)phenyl]-1H-tetrazole derivatives by the Michael addition of chalcones to hydrazine hydrate in presence of acetic acid under conventional heating and microwave irradiation. All the synthesized compounds are characterized by IR, NMR, and mass spectra. The products are screened for their in vitro antimicrobial activity against strains such as Staphylococcus aurous, Bacillus subtilis, Klebsiella pneumonia, Escherichia coli, Aspergillus Niger, Aspergillus flavus, and Fusarium oxysporum. Most of the compounds exhibit high activity.

CuO–NiO bimetallic nanoparticles supported on graphitic carbon nitride with enhanced catalytic performance for the synthesis of 1,2,3-triazoles, bis-1,2,3-triazoles, and tetrazoles in parts per million level

The unification of CuCl2·2H2O and NiCl2·6H2O with the support of graphitic carbon nitride yielded to form an efficient, synergistic, bimetallic nano-catalyst CuO–NiO@g-C3N4. FT-IR, SEM, TEM

An efficient Cu/functionalized graphene oxide catalyst for synthesis of 5-substituted 1H-tetrazoles

The copper nanoparticles (Cu NPs) and amide functionalized graphene oxide (Cu-Amd-RGO) catalyst were prepared. This prepared catalyst (Cu-Amd-RGO) used for the synthesis of tetrazole derivatives. The catalyst (Cu-Amd-RGO) was characterized by field emission scanning electron microscopy (FE-SEM), transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FTIR), and X-ray diffraction analysis (XRD). The average particle size of Cu was found to be 7.6?nm. The Cu-Amd-RGO catalyst exhibited excellent catalytic activity and recyclability for synthesis of tetrazoles.

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.

Practical scale up synthesis of carboxylic acids and their bioisosteres 5-substituted-1H-tetrazoles catalyzed by a graphene oxide-based solid acid carbocatalyst

Herein, catalytic application of a metal-free sulfonic acid functionalized reduced graphene oxide (SA-rGO) material is reported for the synthesis of both carboxylic acids and their bioisosteres, 5-substituted-1H-tetrazoles. SA-rGO as a catalytic material incorporates the intriguing properties of graphene oxide material with additional benefits of highly acidic sites due to sulfonic acid groups. The oxidation of aldehydes to carboxylic acids could be efficiently achieved using H2O2as a green oxidant with high TOF values (9.06-9.89 h?1). The 5-substituted-1H-tetrazoles could also be effectively synthesized with high TOF values (12.08-16.96 h?1). The synthesis of 5-substituted-1H-tetrazoles was corroborated by single crystal X-ray analysis and computational calculations of the proposed reaction mechanism which correlated well with experimental findings. Both of the reactions could be performed efficiently at gram scale (10 g) using the SA-rGO catalyst. SA-rGO displays eminent reusability up to eight runs without significant decrease in its productivity. Thus, these features make SA-rGO riveting from an industrial perspective.

Igneous rock powder as a heterogeneous multi-oxide nano-catalyst for the synthesis of 5-substituted-1H-tetrazoles in polyethylene glycol

The use of igneous rock nano-powder as a heterogeneous and recyclable multi-oxide nano-catalyst synthesizing of 5-substituted-1H-tetrazoles is reported. The igneous rock nano-powder was initially prepared by using the ball-milling method. Then, the structure, morphology, and magnetic properties of the prepared igneous rock nano-powder were characterized with some different spectroscopic, microscopic, and thermogravimetric techniques, such as FTIR, FESEM, XRF, XRD, Histogram, and EDS. The instrumental analyses showed that the prepared igneous rock powder is a mixture of metal oxides, such as Si, Al, Ca, Mg, Fe, Na, Mn, and Sr. It showed an excellent catalytic performance in synthesizing of 5-substituted-1H-tetrazoles through [3 + 2] cycloaddition reaction between sodium azide and nitrile compounds. Various aliphatic and aromatic nitriles and sodium azide were reacted in the presence of a catalytic amount of igneous rock nano-powder at 80 o C temperature in PEG-400. The protocol was simple and rapid, with suitable yields of the obtained tetrazoles. The igneous rock nano-powder is readily accessible, reusable, and holds potential for further application in acid-catalyzed organic syntheses and industrial requirements. Graphic abstract: [Figure not available: see fulltext.]

A Synergistic Magnetically Retrievable Inorganic-Organic Hybrid Metal Oxide Catalyst for Scalable Selective Oxidation of Alcohols to Aldehydes and Ketones

Herein, we report a synergistic silica coated magnetic Fe3O4 catalyst functionalized with nitrogen rich organic moieties and immobilized with cobalt metal ion (FNP-5) for selective oxidation of alcohols to aldehydes and ketones using tert-butyl hydroperoxide (TBHP) as oxidant. The catalyst was rigorously characterized via several techniques which delineate its core-shell structure, magnetic behavior, phase and crystal structure. The Co(III) acts as the active catalytic center for selective oxidation reaction. The control reactions revealed radical mechanistic pathway assisted by the synergism induced by the inorganic-organic hybrid nature of FNP-5. The other features of current protocol involve neat reaction conditions, high TOF values, scalability of product and low E-factor value (1.92). Moreover, FNP-5 could be effortlessly separated via an external magnet, displays recyclability over eight catalytic cycles and exhibits structural integrity even after rigorous use. Overall, these results manifest the understanding of synergistic architectures as sustainable surrogates for selective oxidation reactions.

The anchoring of a Cu(ii)-salophen complex on magnetic mesoporous cellulose nanofibers: green synthesis and an investigation of its catalytic role in tetrazole reactions through a facile one-pot route

Today, most synthetic methods are aimed at carrying out reactions under more efficient conditions and the realization of the twelve principles of green chemistry. Due to the importance and widespread applications of tetrazoles in various industries, especially in the field of pharmaceutical chemistry, and the expansion of the use of nanocatalysts in the preparation of valuable chemical reaction products, we decided to use an (Fe3O4@NFC@NSalophCu)CO2H nanocatalyst in this project. In this study, the synthesis of the nanocatalyst (Fe3O4@NFC@NSalophCu)CO2H was explained in a step-by-step manner. Confirmation of the structure was obtained based on FT-IR, EDX, FE-SEM, TEM, XRD, VSM, DLS, TGA, H-NMR, and CHNO analyses. The catalyst was applied to the synthesis of 5-substituted-1H-tetrazole and 1-substituted-1H-tetrazole derivatives through multi-component reactions (MCRs), and the performance was assessed. With advances in science and technology and increasing environmental pollution, the use of reagents and methods that are less dangerous for the environment has received much attention. Therefore, following green chemistry principles, with the help of the (Fe3O4@NFC@NSalophCu)CO2H salen complex as a nanocatalyst that is recyclable, cheap, safe, and available, the use of water as a green solvent, and reduced reaction times, the synthesis of tetrazoles can be achieved.

Synthesis and Photochemical Properties of Manganese(I) Tricarbonyl Diimine Complexes Bound to Tetrazolato Ligands

Ten manganese(I) tricarbonyl diimine complexes bound to variably functionalised 5-aryl-tetrazolato ligands were prepared, and their photochemical properties were investigated. Upon exposure to light at 365 nm, each complex decomposed to its free diimine and tetrazolato ligands, simultaneously dissociating three CO ligands, as evidenced by changes in the IR spectra of the irradiated complexes over time. The anti-bacterial properties of one of these complexes were tested against Escherichia coli. While the complex displayed no effect on the bacterial growth in the dark, pre-irradiated solutions inhibited bacterial growth. Comparative studies revealed that the antibacterial properties originate from the presence of free 1,10-phenanthroline.

Discovery and optimization of 4-oxo-2-thioxo-thiazolidinones as NOD-like receptor (NLR) family, pyrin domain-containing protein 3 (NLRP3) inhibitors

Aberrant activation of NLRP3 inflammasome is present in a subset of acute and chronic inflammatory diseases. The NLRP3 inflammasome has been recognized as an attractive therapeutic target for developing novel and specific anti-inflammatory inhibitors. Cellular structure-activity relationship-guided optimization resulted in the identification of 4-oxo-2-thioxo-thiazolidinone derivative 9 as a selective and direct small-molecule inhibitor of NLRP3 with IC50 of 2.4 μM, possessing favorable ex vivo and in vivo pharmacokinetic properties. Compound 9 may represent a lead for the development of anti-inflammatory therapeutics for treating NLRP3-driven diseases.