20743-50-4

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
1H-Tetrazole, 1-methyl-5-phenylis used as a precursor in the synthesis of various pharmaceuticals and agrochemicals. Its unique chemical properties and reactivity enable the development of new and effective compounds for medical and agricultural applications.
Used in Specialty Polymers and Materials Production:
1H-Tetrazole, 1-methyl-5-phenylis utilized in the production of specialty polymers and materials, where its chemical properties contribute to the creation of innovative and high-performance products.
Used as a Stabilizer in Propellants and Explosives:
Due to its high heat and hydrolytic stability, 1H-Tetrazole, 1-methyl-5-phenylis used as a stabilizer in propellants and explosives, enhancing their performance and safety.

InChI:InChI=1/C8H8N4/c1-12-8(9-10-11-12)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 
• 21737-87-1 N-methyl benzimidoyl chloride 
• 77-78-1 dimethyl sulfate 
• 131183-03-4 5-phenyltetrazol-1-yl(trimethylsilyl)methane 
• 120-92-3 cyclopentanone 
• 144154-87-0 N-benzimidoyl-N-methyl-hydrazine hydrochloride 
• 5333-86-8 ethyl benzimidate hydrochloride 
• 613-91-2 acetophenone oxime 
• 74305-28-5 ((CH₃(CH₂)3)3P)Co(HONC(CH₃)C(CH₃)NO)2(N₄C(C₆H₅)) 
• 616-38-6 carbonic acid dimethyl ester 
• 88070-48-8 N-methylbenzamide 

Downstream Products

• 131183-03-4 5-phenyltetrazol-1-yl(trimethylsilyl)methane 
• 131183-04-5 1,1-bis(p-tolyl)-2-(5-phenyltetrazol-1-yl)ethanol 
• 24433-71-4 1-ethyl-5-diphenyl-1H-1,2,3,4-tetrazole 
• 120819-50-3 C₉H₁₁N₄⁽¹⁺⁾*CH₃O₄S^(1-) 
• 120836-29-5 C₉H₁₁N₄⁽¹⁺⁾*CH₃O₄S^(1-) 
• 4172-91-2 N-((methylimino)methylene)aniline 
• 131183-00-1 5-phenyltetrazol-1-yldeuteriomethane 
• 69746-32-3 1-methyl-5-(3-nitrophenyl)-tetrazole 
• 101258-12-2 1-methyl-5-(3-aminophenyl)-tetrazole 
• 27770-42-9 methylnitrene 

Relevant academic research and scientific papers

An Expeditious Approach to Tetrazoles from Amides Utilizing Phosphorazidates

A novel method was developed for the synthesis of tetrazoles from amides utilizing diphenyl phosphorazidate or bis(p-nitrophenyl) phosphorazidate as both the activator of amide-oxygen for elimination and azide source. Various amides were converted into th

Substituent-dependent coordination modes of 1-methyl-5-R-tetrazoles in their cupric chloride complexes

A series of cupric chloride complexes with 1-methyl-5-R-tetrazole ligands, where R = NH2, t-Bu, Ph, MeS, CH[dbnd]CH2, MeSO2, were synthesized by interaction of CuCl2·2H2O with the above ligands LNH2, LtBu, LPh, LMeS, LVin, and LMeSO2, respectively. The obtained complexes [Cu(LNH2)3Cl2]·H2O (1), [Cu(LtBu)2Cl2] (2), [Cu(LPh)2Cl2] (3), [Cu(LMeS)2Cl2] (4), [Cu(LVin)Cl2]n (5), and [Cu(LMeSO2)(H2O)Cl2]n (6) were characterized by single crystal X-ray analysis. The effect of C5-substituent on coordination modes of tetrazole ligands and structural motifs of complexes was observed. Complexes 1–4 are mononuclear, with the tetrazole ring N4 coordination. Complex 5 presents 1D coordination polymer, formed at the expense of triple bridge between two neighboring copper(II) cations (double chlorido bridge and the tetrazole ring N3,N4-bridge). In 6, being also 1D coordination polymer, coordination chains are composed of alternating Cu(LMeSO2)2 and Cu(H2O)2 fragments linked by double chlorido bridges. Ligand LMeSO2 shows N3 coordination, being rare among 1,5-disubstituted tetrazoles. The influence of the nature of C5 substituents on coordination features of the obtained complexes is discussed by using quantum-chemical calculations of the electronic structure and basicity of the ligands.

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.

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.

Continuous flow generation and reactions of anhydrous diazomethane using a teflon AF-2400 tube-in-tube reactor

A continuous process for generation, separation, and reactions of anhydrous diazomethane in a tube-in-tube reactor was developed. The inner tube of the reactor is made of hydrophobic, gas-permeable Teflon AF-2400. The diazomethane is formed in the inner tube and then diffuses through the permeable membrane into the outer chamber and subsequently reacts in the solution carried within. This technique allows safe and scalable reactions with dry diazomethane to be performed on a laboratory scale.

Tetrazoles: LIV. Alkylation of 5-aryltetrazoles under microwave activation

The application of microwave activation (MWA) to alkylation of 5-aryltetrazoles with dimethyl sulfate in organic solvents did not considerably affect the selectivity of the process compared to nonactivated procedure. A significant enhancement of the selec

Preparation of 1,5-disubstituted tetrazoles under phase-transfer conditions

Imidoyl chlorides, obtained by common methods from a wide range of aromatic mono- and diamides, are smoothly converted to the corresponding tetrazoles in high yields by treatment with NaN3 under phase-transfer conditions.

A Practical Synthesis of 5-Substituted Tetrazoles.

Nitrosation of N-formyl amidrazones 8a-g with sodium nitrite - aqueous hydrochloric acid gives tetrazoles 10a-g in good yields.

A facile and convenient synthesis of substituted tetrazole derivatives from ketones or α,β-unsaturated ketones.

Triazidochlorosilane (SiCl4-NaN3 in situ) is a new and efficient reagent for the direct conversion of ketones or α,β-unsaturated ketones to the corresponding tetrazole derivatives in nearly quantitative yield.