5-Methyl-1H-tetrazole
[CAS# 4076-36-2]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: 5-Methyl-1H-tetrazole
• Synonyms: 5-Methyl-1H-1,2,3,4-tertazole
• Molecular Formula: C₂H₄N₄
• Molecular Weight: 84.08
• CAS Registry Number: 4076-36-2
• EC Number: 609-862-8
• SMILES: CC1=NNN=N1

Properties

• Density: 1.3±0.1 g/mL, Calc.^*
• Melting point: 142-146 ºC (Expl.)
• Index of Refraction: 1.533, Calc.^*
• Boiling Point: 233.3±23.0 ºC (760 mmHg), Calc.^*
• Flash Point: 116.7±15.6 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS02;GHS07 Danger
• Hazard Statements: H228-H315-H319-H335
• Precautionary Statements: P210-P240-P241-P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P370+P378-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Flammable solids	Flam. Sol.	1	H228
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

5-Methyl-1H-tetrazole is an organic compound with the chemical formula C3H5N3. It is a member of the tetrazole family, which is characterized by a five-membered ring containing four nitrogen atoms and one carbon atom. 5-Methyl-1H-tetrazole is primarily used in chemical synthesis and has applications in various industries, including pharmaceuticals and agriculture.

The discovery of 5-methyl-1H-tetrazole is linked to the broader study of tetrazoles, which have been extensively researched for their diverse reactivity and ability to form complexes with metals. The introduction of the methyl group at the 5-position of the tetrazole ring enhances the compound’s stability and reactivity, making it useful in a range of chemical reactions.

One of the most significant applications of 5-methyl-1H-tetrazole is in the synthesis of pharmaceuticals. It serves as an intermediate in the production of drugs with a variety of therapeutic properties. The tetrazole ring system is often incorporated into pharmaceutical compounds because of its ability to mimic the behavior of carboxylic acid groups, which are found in many bioactive molecules. The presence of the methyl group at the 5-position can alter the pharmacological properties of the resulting drug, such as its bioavailability and metabolic stability.

In addition to its use in pharmaceutical synthesis, 5-methyl-1H-tetrazole is also used in the preparation of certain agrochemicals. It has been incorporated into the design of herbicides, fungicides, and other crop protection agents, where its reactivity with metals and other compounds enhances the effectiveness of the active ingredients.

The compound is also utilized in the preparation of high-energy materials and explosives. The tetrazole ring system is known for its stability and energy density, which makes it valuable in the development of energetic materials that are used in a variety of military and industrial applications.

In summary, 5-methyl-1H-tetrazole is an important chemical intermediate used in the synthesis of pharmaceuticals, agrochemicals, and high-energy materials. Its reactivity and stability make it a versatile building block in the development of a wide range of bioactive and industrial compounds.

References

1978. Condensation of 1-aryl-5-methyltetrazoles with aldehydes. Chemistry of Heterocyclic Compounds, 14(3).
DOI: 10.1007/bf00470575

2018. Synthesis, structure and properties of a multifunctional inorganic-organic hybrid mercury(II) coordination polymer: [Hg2Cl2(mtz)2(H2O)]n. Journal of the Iranian Chemical Society, 16(3).
DOI: 10.1007/s13738-018-1493-x

2020. A Convenient One-Pot Synthesis of 1,5-Disubstituted Tetrazoles Containing an Amino or a Carboxy Group. Russian Journal of Organic Chemistry, 56(5).
DOI: 10.1134/s1070428020050127