Methyl 1,2,4-triazole-3-carboxylate
[CAS# 4928-88-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Ester intermediate
• Name: Methyl 1,2,4-triazole-3-carboxylate
• Synonyms: 1H-1,2,4-Triazole-3-carboxylic acid methyl ester
• Molecular Formula: C₄H₅N₃O₂
• Molecular Weight: 127.10
• CAS Registry Number: 4928-88-5
• EC Number: 480-470-5
• SMILES: COC(=O)C1=NC=NN1

Properties

• Melting point: 196-199 °C (decomp.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-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
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Methyl 1,2,4-triazole-3-carboxylate is an organic compound with the molecular formula C4H5N3O2. This compound belongs to the triazole family and is known for its five-membered ring structure containing three nitrogen atoms. The introduction of this compound into the field of chemical research and its subsequent applications marked major advances in various scientific fields.

The discovery of methyl 1,2,4-triazole-3-carboxylate dates back to the mid-20th century, when heterocyclic compounds were being extensively explored. These compounds were studied for their potential pharmacological properties. Researchers synthesized methyl 1,2,4-triazole-3-carboxylate and characterized its structure through various analytical techniques such as nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry.

One of the major applications of methyl 1,2,4-triazole-3-carboxylate is in the pharmaceutical industry. This compound is a valuable intermediate in the synthesis of various drugs. Its triazole ring structure is essential for the pharmacological activity of a variety of therapeutic agents, especially antifungal and antibacterial drugs. The triazole ring in methyl 1,2,4-triazole-3-carboxylate can be modified to improve the efficacy and safety of these drugs, thereby developing new treatments for infections.

In addition to being a drug intermediate, methyl 1,2,4-triazole-3-carboxylate is used in the agrochemical industry. It is a precursor in the synthesis of fungicides and herbicides, which helps develop compounds that protect crops from fungal diseases and weeds. The stability and reactivity of the triazole ring make it an ideal building block for agrochemicals that can increase crop yields and support sustainable agriculture.

The versatility of methyl 1,2,4-triazole-3-carboxylate extends to its applications in materials science. Researchers have explored its use in the synthesis of coordination polymers and metal-organic frameworks (MOFs). These materials exhibit unique properties, such as high surface area and tunable porosity, making them suitable for gas storage, separation, and catalysis. Incorporating methyl 1,2,4-triazole-3-carboxylate into these frameworks can enhance their stability and functionality, opening new avenues for their practical applications.

In medicinal chemistry, methyl 1,2,4-triazole-3-carboxylate has been studied for its potential as a bioactive compound. Studies have shown that derivatives of this compound exhibit various biological activities, including anticancer, antiviral, and anti-inflammatory effects. By modifying the triazole ring and carboxylate groups, researchers aim to develop novel therapeutic agents with increased potency and selectivity against specific biological targets.

In addition, methyl 1,2,4-triazole-3-carboxylate has found applications in the synthesis of organic electronic materials. These materials are essential for the development of organic light-emitting diodes (OLEDs), organic photovoltaics (OPVs), and organic field-effect transistors (OFETs). The electronic properties of the triazole ring can be fine-tuned to optimize the performance of these devices, thereby facilitating advances in flexible electronics and energy-saving technologies.

Safety considerations for methyl 1,2,4-triazole-3-carboxylate are critical to its handling and application. While it is generally considered safe for use in research and industrial settings, appropriate precautions should be taken to avoid exposure through inhalation, ingestion, or skin contact. Proper storage and handling practices, including the use of personal protective equipment, ensure safe use of this compound.

References

2024. Chromatographic method for rapid determination of triazoles in ribavirin intermediates synthesis: stationary phase comparison. Monatshefte für Chemie - Chemical Monthly.
DOI: 10.1007/s00706-024-03232-1

2022. Synthesis of β-triazolyl sulfones via the reaction of vinyl sulfones with 1,2,4-triazoles under basic conditions. Russian Chemical Bulletin, 71(7).
DOI: 10.1007/s11172-022-3562-7

2005. Methyl 1H-1,2,4-triazole-3-carboxylate. Acta Crystallographica Section E Structure Reports Online, 61(10).
DOI: 10.1107/s1600536805028102