16681-78-0

Basic information

• Product Name: 2H-Tetrazole, 2-methyl-
• Synonyms: 2H-Tetrazole, 2-methyl-;2-Methyl-2H-tetrazole
• CAS NO: 16681-78-0
• Molecular Formula: C₂H₄N₄
• Molecular Weight: 84.08
• Mol File: 16681-78-0.mol

Chemical Properties

• Boiling Point: 171.3 °C at 760 mmHg
• Flash Point: 57.4 °C
• Appearance: /
• Density: 1.4 g/cm³
• Vapor Pressure: 1.41mmHg at 25°C
• Refractive Index: 1.664
• CAS DataBase Reference: 2H-Tetrazole, 2-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Tetrazole, 2-methyl-(16681-78-0)
• EPA Substance Registry System: 2H-Tetrazole, 2-methyl-(16681-78-0)

Safety Data

• Hazardous Substances Data: 16681-78-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2H-Tetrazole, 2-methylis used as a pharmaceutical intermediate for the development of drugs targeting cardiovascular diseases, central nervous system disorders, and cancer treatment. Its unique chemical structure and properties contribute to the design and synthesis of novel therapeutic agents with improved efficacy and safety profiles.
Used in Agrochemical Industry:
In the agrochemical sector, 2-methyl-2H-tetrazole serves as a key component in the formulation of various pesticides and herbicides. Its ability to form stable complexes with metal ions and its reactivity with organic compounds make it a valuable ingredient in the development of effective and environmentally friendly agrochemical products.
Used in Energetic Materials:
2H-Tetrazole, 2-methylis utilized in the production of energetic materials, such as explosives and propellants, due to its high energy content and stability. Its incorporation into these materials enhances their performance and safety characteristics, making them suitable for various applications in the defense and aerospace industries.
Used in Organic Synthesis:
As a building block in organic synthesis, 2-methyl-2H-tetrazole is employed in the synthesis of a wide range of organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its versatile reactivity and stability make it an attractive candidate for the development of new chemical entities with potential applications in various industries.

InChI:InChI=1/C2H4N4/c1-6-4-2-3-5-6/h2H,1H3

Upstream product

• 288-94-8 1H-tetrazole 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 13175-00-3 2-methyl-2H-1,2,3,4-tetrazole-5-carboxylic acid 
• 288-94-8 2H-tetrazole 

Downstream Products

• 107403-54-3 3-Methyl-1-[2-(4-nitro-phenyl)-2-oxo-ethyl]-3H-tetrazol-1-ium; bromide 
• 107403-52-1 3-Methyl-1-(2-oxo-2-phenyl-ethyl)-3H-tetrazol-1-ium; bromide 
• 107403-53-2 1-[2-(4-Bromo-phenyl)-2-oxo-ethyl]-3-methyl-3H-tetrazol-1-ium; bromide 
• 1025840-65-6 [(S)-2-Methyl-1-(2-methyl-2H-tetrazole-5-carbonyl)-propyl]-carbamic acid benzyl ester 

Relevant articles and documents

Synthesis and structure of 1-tert-butyl-3-R-tetrazolium salts

An effective method was developed for the synthesis of 1,3-disubstituted tetrazolium salts by the quaternization of 2-monosubstituted tetrazoles, including functionally substituted compounds, with tert-butanol in 72% perchloric acid. An X-ray diffraction

2-Methyl-substituted monotetrazoles in copper(ii) perchlorate complexes: manipulating coordination chemistry and derived energetic properties

A proposed correlation between coordination chemistry and deduced energetic properties (thermal behaviour, and sensitivities towards mechanical and optical stimuli) of copper(ii) complexes is investigated. Starting from a system comprising Cu(ClO4)2 and either of the ligands 2-methyl-5-aminotetrazole (1, 2-MAT) or 2-methyl-5H-tetrazole (2, 2-MTZ), typically altered parameters like the metal(ii) centre, ligand, or counterion were predefined. Instead, solely slight changes in ligand concentration and the solvent system were implemented in order to provide an insight into structure-property relationships of energetic coordination compounds (ECC) of this type. As a result, five highly energetic complexes [Cu(H2O)2(2-MAT)4](ClO4)2·H2O (3), [Cu(H2O)2(2-MAT)4](ClO4)2 (4), [Cu(H2O)2(2-MAT)4](ClO4)2·2 2-MAT (5), [Cu(ClO4)2(H2O)2(2-MAT)2] (6), and [Cu(H2O)2(2-MTZ)4](ClO4)2 (7) were synthesized and, except for 5, elaborately characterized. Besides structural elucidation via X-ray diffraction, NIR-spectroscopy, differential thermal analysis (DTA), standard sensitivity measurements (impact, friction, and electrostatic discharge), UV/vis-spectroscopy, and optical initiation experiments were conducted to deduce a precise relationship between coordination chemistry and the consequential energetic characteristics of these complexes.

Coordination chemistry with 1-methyl-5: H -tetrazole: Cocrystallization, laser-ignition, lead-free primary explosives-one ligand, three goals

The synthesis and characterization of 1-methyl-5H-tetrazole (1, MTZ) from 1,5H-tetrazole and methyl iodide is achieved. This neutral ligand was evaluated for its use in energetic transition metal complexes. The formation of complexes is a valuable concept because of their easy synthesis and the large number of possible combinations: (i) metal, (ii) ligand, and (iii) anion. A series of 31 new complexes based on MTZ as the ligand was prepared in order to tune their optical properties and sensitivity values by using seven different metals (Mn2+, Fe2+, Co2+, Ni2+, Cu2+, Zn2+, and Ag+) and six different anions (chloride, nitrate, perchlorate, cyanodinitromethanide, picrate, and styphnate). This variation allows tailoring of the energetic properties of the desired molecule toward e.g. suitable primary explosives or laser-ignitable materials. Obtained compounds were characterized by low temperature single crystal X-ray diffraction, IR spectroscopy, elemental analysis and thermal analysis (DTA, DSC and TGA). The sensitivities toward external stimuli (impact, friction and electrostatic discharge) were determined according to the Bundesamt für Materialforschung und -prüfung (BAM) standard methods. These complexes have been characterized in laser ignition experiments and as new primary explosives. UV-vis measurements of selected complexes were carried out to get a possible insight into the laser initiation mechanism. For the first time a large number of compounds with sensitivities ranging from insensitive to very sensitive were synthesized to give a wide range of new materials for different possible applications.

6-O-substituted erythromycin derivatives having improved gastrointestinal tolerance

Compounds having formula (I) are useful for treating bacterial infections while avoiding the concomitant liability of gastrointestinal intolerance. Compositions containing the compounds and methods of treatment using the compounds are also disclosed.

Antibacterial compounds with improved pharmacokinetic profiles

Antibacterial compounds with improved pharmacokinetic profiles having formula (I) and salts, prodrugs, and salts of prodrugs thereof, processes for making the compounds and intermediates used in the processes, compositions containing the compounds, and methods for prophylaxis and treatment of bacterial infections using the compounds are disclosed.

Cannabinoid receptor modulators, their processes of preparation, and use of cannabinoid receptor modulators for treating respiratory and non-respiratory diseases

Use of a compound for treating a respiratory disease in a mammal wherein the compound is a cannabinoid receptor modulator is disclosed. Compounds useful as cannabinoid receptor modulators for treating respiratory and non-respiratory leukocyte-activation associated diseases comprise compounds of formula (I), in which A and B are nitrogen or carbon, provided only one of A and B is nitrogen; and R1-R6 are as defined in the specification, wherein R2 with R5 may form a ring, and/or two R4 groups may form a six-membered aryl or heteroaryl ring, optionally having a substituent R6 forming a ring with R3.

Alkylation, Acylation and Silylation of Azoles

Performing alkylation, acylation and silylation reactions in separate deprotonation and nucleophilic displacement steps allows for better control of reaction conditions and facilitates problem handling in these processes.In the alkylation of azoles the alkylating agents and solvents possess individual reaction capabilities which seem to be approximately additive.Monoalkylation occurs if the sum of the normalized reaction potentials is equal or larger than the pKa value of the azole.Dialkylation is avoided by keeping the sum of the normalized reaction potentials below the pKa value of the alkylazole.The applicability of these principles is demonstrated by the development of effective procedures for the methylation, benzylation, acetylation, methoxycarbonylation and trimethylsilylation of azoles.

INTRODUCTION OF SUBSTITUENTS INTO 5-MEMBERED AZA-HETEROAROMATICS

With emphasis on mono- and regio-selectively, methods for introduction of substituents at nitrogen and carbon atoms of 5-membered aza-heteroaromatics have been developed.The methods involve application of activation and of assistant groups for direction and protection.Activation has been achieved by the use of quaternary azolium ions and azol-N-oxides as reactive intermediates.If necessary, the N-oxides were further activated by alkylation or acylation.

Positional Selectivity of the Methylation of 5-Substituted Tetrazolate Anions

The methylation of a series of 15 sodium 5-substituted tetrazolates using iodomethane in acetone/water (4:1) has been studied.The reaction yields both 1- and 2-methyl products, and the ratio of these products is discussed in terms of the nature of the 5-substituent.Electronic and steric effects dominate the reaction pathway; both increased substituent electronegativity and steric bulk lead to predominant methylation at N 2.Sodium 5-ethoxycarbonyltetrazolate (3n) goes against this trend and an intermediate is proposed where the incoming electrophile is associated with the ester carbonyl group.

TETRAZOLES. XVI. ALKYLATION OF TETRAZOLES UNDER THE CONDITIONS OF PHASE-TRANSFER CATALYSIS

The alkylation of tetrazole and 5-substituted tetrazoles with dimethyl sulfate and methyl iodide in the two-phase methylene chloride-water system in the presence of tetrabutylammonium bromide was investigated.The alkylation of tetrazoles with methyl iodide takes place in the organic phase, while that with dimethyl sulfate takes place both in the organic and in the aqueous phases.The ratio of the isomeric tetrazoles formed during the alkylation of 5-aryltetrazoles by methyl iodide correlate with the substituent constants ?.The use of phase-transfer catalysis during the alkylation of tetrazoles does not lead to a change in the selectivity of the reaction.