20743-49-1

Basic information

• Product Name: 2-methyl-5-phenyl-2h-tetrazole
• Synonyms: 2H-Tetrazole, 2-methyl-5-phenyl-;2-Methyl-5-phenyltetrazole
• CAS NO: 20743-49-1
• Molecular Formula: C₈H₈N₄
• Molecular Weight: 160.18
• Mol File: 20743-49-1.mol

Chemical Properties

• Boiling Point: 313.3°Cat760mmHg
• Flash Point: 143.3°C
• Appearance: /
• Density: 1.24g/cm³
• Vapor Pressure: 0.000501mmHg at 25°C
• Refractive Index: 1.657
• CAS DataBase Reference: 2-methyl-5-phenyl-2h-tetrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methyl-5-phenyl-2h-tetrazole(20743-49-1)
• EPA Substance Registry System: 2-methyl-5-phenyl-2h-tetrazole(20743-49-1)

Safety Data

• Hazardous Substances Data: 20743-49-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-methyl-5-phenyl-2h-tetrazole is used as a pharmaceutical candidate for its potential biological and pharmacological activities. It is being studied for its antimicrobial and antifungal properties, which can be utilized in the development of new drugs to combat resistant infections.
Used in Chemical Research:
In the field of chemical research, 2-methyl-5-phenyl-2h-tetrazole is used as a versatile compound for the synthesis of various organic compounds. Its unique structure and properties make it a valuable precursor in the development of new chemical entities.
Used in Corrosion Inhibition:
2-methyl-5-phenyl-2h-tetrazole is also being investigated for its potential use as a corrosion inhibitor. Its ability to protect materials from corrosion can be applied in various industries, such as manufacturing and construction, to extend the lifespan of equipment and structures.
Used in Materials Science:
In materials science, 2-methyl-5-phenyl-2h-tetrazole is explored for its potential applications in the development of new materials with enhanced properties. Its unique chemical structure can contribute to the creation of materials with improved performance in various applications.

InChI:InChI=1/C8H8N4/c1-12-10-8(9-11-12)7-5-3-2-4-6-7/h2-6H,1H3

Upstream product

• 18039-42-4 5-Phenyl-1H-tetrazole 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 67-64-1 acetone 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 80-11-5 N-methyl-N-nitrosotoluene-p-sulfonamide 
• 80-15-9 Cumene hydroperoxide 
• 18039-42-4 5-phenyl-2H-1,2,3,4-tetrazole 
• 13393-68-5 1,1-dimethylbutyl hydroperoxide 
• 75-91-2 tert.-butylhydroperoxide 
• 74-89-5 methylamine 
• 13466-29-0 1-benzylidene-2-methylhydrazine 
• 100-52-7 benzaldehyde 
• 67-56-1 methanol 

Downstream Products

• 64017-21-6 3,5-diphenyl-1-methyl-1H-1,2,4-triazole 
• 87277-51-8 1-methyl-5-(4-chlorophenyl)-3-phenyl-1H-1,2,4-triazole 
• 93742-43-9 2-(β-hydroxyethyl)-5-phenyltetrazole 
• 131183-01-2 5-phenyl-2-((trimethylsilyl)methyl)-2H-tetrazole 
• 90145-16-7 1-Methyl-3,4,5-triphenyl-2-pyrazolin 
• 134792-44-2 1-(4-methoxyphenyl)-2-(5-phenyl-2H-tetrazol-2-yl)ethanol 
• 134792-25-9 1-(5-phenyltetrazol-2-yl)butan-2-ol 
• 120819-50-3 C₉H₁₁N₄⁽¹⁺⁾*CH₃O₄S^(1-) 
• 90145-29-2 1-Methyl-3,4-diphenylpyrazol-5-carbonsaeure-methylester 
• 90145-30-5 1-Methyl-3,5-diphenylpyrazol-4-carbonsaeure-methylester 
• 90145-27-0 1-Methyl-3,4-diphenyl-2-pyrazolin-5-carbonsaeure-methylester 
• 90145-28-1 1-Methyl-3,5-diphenyl-2-pyrazolin-4-carbonsaeure-methylester 
• 100-42-5 styrene 
• 4172-91-2 N-((methylimino)methylene)aniline 

Relevant articles and documents

Iridium(III) complexes with phenyl-tetrazoles as cyclometalating ligands

Ir(III) cationic complexes with cyclometalating tetrazolate ligands were prepared for the first time, following a two-step strategy based on (i) a silver-assisted cyclometalation reaction of a tetrazole derivative with IrCl3 affording a bis-cyclometalated solvato-complex P ([Ir(ptrz)2(CH3CN)2]+, Hptrz = 2-methyl-5-phenyl-2H-tetrazole); (ii) a substitution reaction with five neutral ancillary ligands to get [Ir(ptrz)2L]+, with L = 2,2′-bypiridine (1), 4,4′-di-tert-butyl-2,2′-bipyridine (2), 1,10-phenanthroline (3), and 2-(1-phenyl-1H-1,2,3-triazol-4-yl)pyridine (4), and [Ir(ptrz)2L2]+, with L = tert-butyl isocyanide (5). X-ray crystal structures of P, 2, and 3 were solved. Electrochemical and photophysical studies, along with density functional theory calculations, allowed a comprehensive rationalization of the electronic properties of 1-5. In acetonitrile at 298 K, complexes equipped with bipyridine or phenanthroline ancillary ligands (1-3) exhibit intense and structureless emission bands centered at around 540 nm, with metal-to-ligand and ligand-to-ligand charge transfer (MLCT/LLCT) character; their photoluminescence quantum yields (PLQYs) are in the range of 55-70%. By contrast, the luminescence band of 5 is weak, structured, and blue-shifted and is attributed to a ligand-centered (LC) triplet state of the tetrazolate cyclometalated ligand. The PLQY of 4 is extremely low (a nonemissive triplet metal-centered ( 3MC) state. In rigid matrix at 77 K, all of the complexes exhibit intense luminescence. Ligands 1-3 are also strong emitters in solid matrices at room temperature (1% poly(methyl methacrylate) matrix and neat films), with PLQYs in the range of 27-70%. Good quality films of 2 could be obtained to make light-emitting electrochemical cells that emit bright green light and exhibit a maximum luminance of 310 cd m-2. Tetrazolate cyclometalated ligands push the emission of Ir(III) complexes to the blue, when compared to pyrazolate or triazolate analogues. More generally, among the cationic Ir(III) complexes without fluorine substituents on the cyclometalated ligands, 1-3 exhibit the highest-energy MLCT/LLCT emission bands ever reported.

Alkylation of 5-Substituted 1 H-Tetrazoles via the Diazotization of Aliphatic Amines

A new alkylation reaction of monosubstituted tetrazoles via the diazotization of aliphatic amines is reported. This method enables preferential formation of 2,5-disubstituted tetrazoles. A one-pot 1,3-dipolar cycloaddition/diazotization sequence starting from widely available nitriles is also described. Azide residues are quenched in the second step with the nitrite reagent, thus limiting the intrinsic risk associated with trimethylsilyl azide. The reaction conditions were compatible with several functional groups, including thiocyanates, which afford preferentially disubstituted 2-alkyl-5-(substituted-thio)tetrazoles.

Bu4NI-Catalyzed, Radical-Induced Regioselective N-Alkylations and Arylations of Tetrazoles Using Organic Peroxides/Peresters

Bu4NI-catalyzed regioselective N2-methylation, N2-Alkylation, and N2-Arylation of tetrazoles have been achieved using tert-butyl hydroperoxide (TBHP) as the methyl source, alkyl diacyl peroxides as the primary alkyl source, alkyl peresters as the secondary and tertiary alkyl sources, and aryl diacyl peroxides as the arylating source. These reactions proceed without pre-functionalization of tetrazole and in the absence of any metal catalysts. Here, peroxides serve the dual role of oxidants as well as alkylating or arylating agents. Based on DFT calculations, it was found that spin density, transition-state barriers (kinetic control), and thermodynamic stability of the products (thermodynamic control) play essential roles in the observed regioselectivity during N-Alkylation. This radical-mediated process is amenable to a broad range of substrates and provides products in moderate to good yields.

Ruthenium-Catalyzed meta-Selective C?H Nitration of Biologically Important Aryltetrazoles

The first example of tetrazole-directed meta-selective C?H nitration is described. This transformation provided a straightforward approach for the synthesis of biologically important m-nitroaryltetrazoles in moderate to excellent yields with good functional group compatibility. In addition, new metallo-β-lactamase inhibitors were obtained by further transformation of the synthesized m-nitroaryltetrazoles. (Figure presented.).

Discovery of mercaptopropanamide-substituted aryl tetrazoles as new broad-spectrum metallo-β-lactamase inhibitors

β-Lactam antibiotic resistance mediated by metallo-β-lactamases (MBL) has threatened global public health. There are currently no available inhibitors of MBLs for clinical use. We previously reported the ruthenium-catalyzed meta-selective C-H nitration synthesis method, leading to some meta-mercaptopropanamide substituted aryl tetrazoles as new potent MBL inhibitors. Here, we described the structure-activity relationship of meta- and ortho-mercaptopropanamide substituted aryl tetrazoles with clinically relevant MBLs. The resulting most potent compound 13a showed IC50 values of 0.044 μM, 0.396 μM and 0.71 μM against VIM-2, NDM-1 and IMP-1 MBL, respectively. Crystallographic analysis revealed that 13a chelated to active site zinc ions via the thiol group and interacted with the catalytically important residues Asn233 and Tyr67, providing further structural information for the development of thiol based MBL inhibitors. This journal is

ACLY INHIBITORS AND USES THEREOF

The present invention provides compounds useful as inhibitors of ATP citrate lyase (ACLY), compositions thereof, and methods of using the same.

Preparation of 5-Aryl-2-Alkyltetrazoles with Aromatic Aldehydes, Alkylhydrazine, Di-tert-butyl Azodicarboxylate, and [Bis(trifluoroacetoxy)iodo]benzene

A variety of 5-aryl-2-methyltetrazoles and 5-aryl-2-benzyltetrazoles were directly prepared in good to moderate yields by the reaction of aromatic aldehydes with methylhydrazine and benzylhydrazine, followed by treatment with di-tert-butyl azodicarboxylate and [bis(trifluoroacetoxy)iodo]benzene in a mixture of dichloromethane and 2,2,2-trifluoroethanol at room temperature. The present method is a novel one-pot preparation of 5-aryl-2-methyltetrazoles and 5-aryl-2-benzyltetrazoles through a [2N + 2N] combination under transition metal-free and mild conditions.

Alkylation of 5-substituted NH-tetrazoles by alcohols in the superacid CF3SO3H

Reactions of 5-substituted NH-tetrazoles with alcohols in the superacid CF3SO3H have been studied. Both the structure of the tetrazole and the nature of alcohol were found to dramatically influence the selectivity of the reaction and yields of products. Tetrazoles bearing phenyl, electron-donating aryl, or benzyl groups at the 5-position, have been alkylated using various alcohols (including MeOH and EtOH) in CF3SO3H upon heating at 60 °C for 0.3-12 h to afford 2-alkyl-2H-tetrazoles in 30-98% yields.

An Environmentally Friendly Method for N-Methylation of 5-Substituted 1H-Tetrazoles with a Green Methylating Reagent: Dimethyl Carbonate

An environmentally friendly method was established for the N-methylation of the 5-substituted 1H-tetrazoles with a green reagent: DMC. DABCO was the optimal catalyst, and hazardous chemicals were avoided in this protocol. A plausible catalytic mechanism is proposed, which consists of a DABCO-activated process and a thermally induced rearrangement of tetrazole carbamates.

Rhodium-catalyzed olefination of aryl tetrazoles via direct C-H bond activation

Rh(III)-catalyzed direct olefination reaction via aromatic C-H bond activation is described using tetrazole as the directing group. This reaction provides a straightforward way for the synthesis of ortho-alkenyl aryl tetrazoles. Various functional groups tolerate the reaction conditions and afford the corresponding products in moderate to excellent yields.