3440-99-1

Basic information

• Product Name: 5-(3-Bromophenyl)-1H-tetrazole
• Synonyms: 5-(3-BROMOPHENYL)-1H-TETRAZOLE;5-(3-BROMOPHENYL)-1H-TETRAZOLE(3-BPHT)
• CAS NO: 3440-99-1
• Molecular Formula: C₇H₅BrN₄
• Molecular Weight: 225.05
• EINECS: -0
• Mol File: 3440-99-1.mol

Chemical Properties

• Melting Point: 150-152°C
• Boiling Point: 390.7°Cat760mmHg
• Flash Point: 190.1°C
• Appearance: /
• Density: 1.745g/cm³
• Vapor Pressure: 2.61E-06mmHg at 25°C
• Refractive Index: 1.653
• Storage Temp.: Room temperature.
• BRN: 141258
• CAS DataBase Reference: 5-(3-Bromophenyl)-1H-tetrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(3-Bromophenyl)-1H-tetrazole(3440-99-1)
• EPA Substance Registry System: 5-(3-Bromophenyl)-1H-tetrazole(3440-99-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 3440-99-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-(3-Bromophenyl)-1H-tetrazole is used as a precursor for the synthesis of energetic materials due to its high energy content, which makes it a promising candidate for the development of new pharmaceutical compounds with enhanced properties.
Used in Agrochemical Industry:
In the agrochemical sector, 5-(3-Bromophenyl)-1H-tetrazole is utilized as a building block for the creation of novel agrochemicals, potentially improving the efficiency and selectivity of pest control agents.
Used in Materials Science:
5-(3-Bromophenyl)-1H-tetrazole is employed as a component in the development of high-energy density materials for applications in materials science, where its energy-rich properties can contribute to advancements in energy storage and conversion technologies.
Used as an Enzyme Inhibitor:
5-(3-Bromophenyl)-1H-tetrazole is used as an enzyme inhibitor, leveraging its chemical structure to modulate enzyme activity, which can be beneficial in the design of drugs targeting specific biochemical pathways.
Used as a Ligand in Coordination Chemistry:
In coordination chemistry, 5-(3-Bromophenyl)-1H-tetrazole serves as a ligand, contributing to the formation of coordination complexes with potential applications in catalysis, sensing, and other areas of chemical research and development.

InChI:InChI=1/C7H5BrN4/c8-6-3-1-2-5(4-6)7-9-11-12-10-7/h1-4H,(H,9,10,11,12)

Upstream product

• 6952-59-6 3-cyanobromobenzene 
• 3132-99-8 m-bromobenzoic aldehyde 

Downstream Products

• 945239-00-9 1-(benzo[d][1,3]dioxol-5-yl)-N-(6-methyl-3'-(2H-tetrazol-5-yl)biphenyl-3-yl)cyclopropanecarboxamide 
• 660859-36-9 4-[5-(3-bromophenyl)tetrazol-2-ylmethyl]benzenesulfonic acid sodium salt 
• 660859-37-0 {4-[5-(3-bromophenyl)tetrazol-2-ylmethyl]benzyl}phosphonic acid dimethyl ester 
• 1170215-06-1 2-(3-bromophenyl)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 
• 348125-04-2 2-(3-bromophenyl)-5-p-tolyl-1,3,4-oxadiazole 

Relevant articles and documents

Coupling ofN-tosylhydrazones with tetrazoles: synthesis of 2-β-d-glycopyranosylmethyl-5-substituted-2H-tetrazole type glycomimetics

Coupling reactions ofO-peracylated 2,6-anhydro-aldose tosylhydrazones (C-(β-d-glycopyranosyl)formaldehyde tosylhydrazones) with tetrazoles were studied under metal-free conditions using thermic or microwave activation in the presence of different bases. The reactions proved highly regioselective and gave the corresponding, up-to-now unknown 2-β-d-glycopyranosylmethyl-2H-tetrazoles in 7-67% yields. The method can be applied to get new types of disaccharide mimetics, 5-glycosyl-2-glycopyranosylmethyl-2H-tetrazoles, as well. Galectin binding studies withC-(β-d-galactopyranosyl)formaldehyde tosylhydrazone and 2-(β-d-galactopyranosylmethyl)-5-phenyl-2H-tetrazole revealed no significant inhibition of any of these lectins.

Copper-based catalysts derived from salen-type ligands: Synthesis of 5-substituted-1: H-tetrazoles via [3+2] cycloaddition and propargylamines via A3-coupling reactions

Base-metal copper(ii) complexes derived from unsymmetrical salen-type ligands were designed and synthesized using ligands L1H to L4H in moderate yield. The synthesized unsymmetrical ligands L1H to L4H and the corresponding copper complexes (1-4) were characterized by UV-visible, IR and ESI-MS spectroscopic studies. Molecular structures of complexes 1, 2 and 4 were determined by X-ray crystallography. Copper complexes 1-4 were employed as catalysts for [3+2] cycloaddition and A3-coupling reactions. The mutual approach of salen-type ligands and metals via active participation of ligands allow to achieve the catalytic reactions. Reaction pathways were proposed and possible intermediate species during the catalytic cycle were successfully characterized by ESI-MS spectroscopic studies. This journal is

TMSN3-Bu2Sn(OAc)2: A modified and mild reagent system for Wittenberger tetrazole-synthesis

Treatments of various nitriles with TMSN3 and Bu2Sn(OAc)2 at 30 °C in benzene for 60 h yielded the corresponding 5-substituted 1H-tetrazoles in good to excellent yields. This method is a mild and efficient alternative reagent system for Wittenberger tetrazole-synthesis that uses TMSN3 and Bu2SnO in toluene at high temperature (93–110 °C) for 24–72 h.

NOVEL ARYL OR HETEROARYL TRIAZOLONE DERIVATIVES OR SALTS THEREOF, OR PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME

The present technology provides aryl or heteroaryl triazolone derivatives or pharmaceutically acceptable salts thereof, preparation processes thereof, pharmaceutical compositions comprising the same, and the use thereof. The aryl or heteroaryl triazolone derivatives or their pharmaceutically acceptable salts exhibit selective inhibitory activity on VAP-1 and therefore can be usefully applied, e.g., for the treatment and prophylaxis of nonalcoholic hepatosteatosis (NASH).

Cationic organotin cluster [t-Bu2Sn(OH)(H2O)]2 2+2OTf?-catalyzed one-pot three-component syntheses of 5-substituted 1H-tetrazoles and 2,4,6-triarylpyridines in water

The cationic organotin cluster [t-Bu2Sn(OH)(H2O)]2 2+2OTf? is easy to prepare and stable in air. The catalytic activity of [t-Bu2Sn(OH)(H2O)]2 2+2OTf? as a neutral organotin Lewis acid catalyst is probed through the one-pot three-component syntheses of 5-substituted 1H-tetrazoles from aldehydes, hydroxylamine hydrochloride and sodium azide, and of 2,4,6-triarylpyridines from aromatic aldehydes, substituted acetophenones and ammonium acetate. The reactions proceed well in the presence of 1?mol% of [t-Bu2Sn(OH)(H2O)]2 2+2OTf? in water and provide the corresponding 5-substituted 1H-tetrazoles and 2,4,6-triarylpyridines in good to excellent yields. The method reported has several advantages such as the catalyst being neutral, low catalyst loading and use of water as a green solvent.

Humic acid as an efficient and reusable catalyst for one pot three-component green synthesis of 5-substituted 1: H -tetrazoles in water

Humic acid is a non toxic, inexpensive, easily available high-molecular weight polymer. A simple and facile one pot three-component synthesis of 5-substituted 1H-tetrazoles from aldehydes, hydroxyamine hydrochloride and sodium azide using humic acid as an efficient catalyst in water is described. The method reported has several advantages such as high to excellent yields, easy work-up, mild reaction conditions, use of water as a green solvent, and a commercially available, nontoxic and reusable catalyst.

Copper(II)-faciliated synthesis of substituted thioethers and 5-substituted 1H-tetrazoles: Experimental and theoretical studies

Benzoylhydrazine based Schiff base-ligated two new copper(II) complexes, [Cu(L1)2] (1) and [Cu(L2)2] (2) were synthesized by the reaction of Cu(CH3COO)2·H2O with respective Schiff base ligand 1-[(4-nitrophenyl)ethylidene] benzohydrazide (HL1) or 1-[(4-methoxyphenyl)ethylidene] benzohydrazide (HL2). Both complexes were isolated as greenish solid and fully characterized by elemental analysis, FT-IR, EPR, thermo-gravimetric (TG) analysis and Cyclic Voltammetry. The molecular structures of both complexes have also been determined by single crystal X-ray crystallography, which confirmed the coordination of Schiff base ligands through N, O donor atoms and distorted square planar geometry around the Cu(II) ion. Both complexes were found to be good homogeneous catalysts for the synthesis of a wide range of substituted thioethers and 5-substituted 1H-tetrazoles in 92% and 93% yield, respectively, at a low catalyst loading (0.5 mol%). The bond angles and distances, as discerned from the DFT calculations, commusurated with the experimental findings. The energy difference between the HOMO and the LUMO, calculated from DFT studies, was found to be 5.645 eV and 6.459 eV for complex 1 and complex 2, respectively. These results are in harmony with the observed higher catalytic activity of complex 1.

Synthesis of tetrazoles, triazoles, and imidazolines catalyzed by magnetic silica spheres grafted acid

The magnetically separable catalysts are used in the synthesis of N-containing heterocycles, including tetrazoles, triazoles, and imidazolines. The magnetic silica sphere grafted sulfonic acid (MSS-SO3H) is suitable for the synthesis of 1,2,3-triazole via the cycloaddition of nitroalkene with NaN3, whereas the zinc-modified silica sphere catalyst (MSS-SO3Zn) is more suitable for the synthesis of tetrazoles. The MSS-SO3Zn catalyst also works well for the synthesis of 2-substituted imidazoline via the condensation of nitriles with ethylenediamine. Both of the MSS-SO3H and MSS-SO3Zn catalysts can be recovered easily by a magnet, and they can be reused without further tedious activation.

Unprecedented formation of a μ-oxobridged polymeric copper(II) complex: Evaluation of catalytic activity in synthesis of 5-substituted 1H-tetrazoles

The reaction of CuCl2·2H2O with Schiff base ligand, 4-[(2-hydroxy-3-methoxybenzylidene)amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3-one] (hmdpH), in 1:1 molar ratio led to a novel and unprecedented oxo-bridged polymeric copper (II) complex, [Cu(μ-O) (hmdp)]n. The complex was isolated as crystalline solid and characterized by FTIR, UV–visible and EPR spectroscopic techniques. The molecular structure of the complex was also determined by single crystal X-ray diffraction studies. The formation of the complex is unique and unprecedented in the sense that one of the CH3 group of the 4-aminoantipyrene unit of the Schiff base ligand is oxidized in situ to CH2OH, during the complex formation. The catalytic potential of the complex has been demonstrated in the synthesis of a series of 5-substituted 1H-tetrazoles via [3 + 2]-cycloaddition reactions of substituted benzonitriles and sodium azide in ethylene glycol.

Engineering a Cu-MOF Nano-Catalyst by using Post-Synthetic Modification for the Preparation of 5-Substituted 1H-Tetrazoles

A new nano scale Cu-MOF has been obtained via post-synthetic metalation by immersing a Zn-MOF as a template in DMF solutions of copper(II) salts. The Cu-MOF serves as recyclable nano-catalyst for the preparation of 5-substituted 1H-tetrazoles via [3?+?2] cycloaddition reaction of various nitriles and sodium azide in a green medium (PEG). The post-synthetic metalated MOF were characterized by FT-IR spectroscopy, powder X-ray diffraction (PXRD), atomic absorption spectroscopy (AAS), and energy dispersive X-ray spectroscopy (EDX) techniques. The morphology and size of the nano-catalyst were determined by field emission scanning electron microscopy (FE-SEM).