3-Chloromethyl-1,2,4-triazolin-5-one
[CAS# 252742-72-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Ketones
• Name: 3-Chloromethyl-1,2,4-triazolin-5-one
• Synonyms: 5-Chloromethyl-2,4-dihydro-[1,2,4]triazol-3-one
• Molecular Formula: C₃H₄ClN₃O
• Molecular Weight: 133.54
• CAS Registry Number: 252742-72-6
• EC Number: 607-678-2
• SMILES: C(C1=NNC(=O)N1)Cl

Properties

• Density: 1.8±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.711, Calc.^*

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

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08 Danger
• Risk Statements: H290-H302-H314-H318-H319-H335-H341-H351
• Safety Statements: P203-P234-P260-P261-P264-P264+P265-P270-P271-P280-P301+P317-P301+P330+P331-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P318-P319-P321-P330-P337+P317-P363-P390-P403+P233-P405-P406-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Carcinogenicity	Carc.	2	H351
Acute toxicity	Acute Tox.	4	H302
Germ cell mutagenicity	Muta.	2	H341
Serious eye damage	Eye Dam.	1	H318
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

3-Chloromethyl-1,2,4-triazolin-5-one is a heterocyclic compound notable for its diverse applications in organic synthesis and pharmaceutical chemistry. With the molecular formula C4H5ClN4O, this compound features a triazole ring, a nitrogen-rich five-membered heterocycle that imparts unique chemical properties. The discovery of 3-chloromethyl-1,2,4-triazolin-5-one dates back to the late 20th century when researchers began to explore triazole derivatives for their biological and synthetic utility.

The synthesis of 3-chloromethyl-1,2,4-triazolin-5-one typically involves the chloromethylation of 1,2,4-triazolin-5-one, a reaction that introduces a chloromethyl group at the 3-position of the triazole ring. This modification enhances the reactivity of the compound, allowing it to serve as a versatile building block in the construction of more complex molecular structures. The chloromethyl group is particularly valuable due to its potential for nucleophilic substitution reactions, making it a useful intermediate in organic synthesis.

One of the primary applications of 3-chloromethyl-1,2,4-triazolin-5-one lies in the development of agrochemicals, including herbicides and fungicides. The compound exhibits biological activity that can be harnessed for crop protection, thereby contributing to agricultural productivity. Researchers have investigated various derivatives of 3-chloromethyl-1,2,4-triazolin-5-one to optimize their efficacy and selectivity against target pests and pathogens, leading to the discovery of several promising candidates in agrochemical formulations.

In addition to its applications in agriculture, 3-chloromethyl-1,2,4-triazolin-5-one has garnered interest in medicinal chemistry. The triazole moiety is known for its ability to interact with biological targets, and modifications to the triazolin-5-one framework can yield compounds with enhanced pharmacological profiles. Researchers have synthesized various derivatives of 3-chloromethyl-1,2,4-triazolin-5-one and evaluated their activity against a range of biological targets, including enzymes and receptors involved in disease processes. This exploration has led to the identification of potential drug candidates for conditions such as cancer and infectious diseases.

The compound's utility in material science is also being explored. Its incorporation into polymer matrices can enhance the properties of materials, such as thermal stability and mechanical strength. As research continues in this area, the development of functionalized polymers containing 3-chloromethyl-1,2,4-triazolin-5-one could lead to innovative materials with applications in coatings, adhesives, and composites.

However, the handling and application of 3-chloromethyl-1,2,4-triazolin-5-one require careful consideration of safety and environmental factors. As a chlorinated compound, it may pose risks associated with chlorinated organic chemicals. Therefore, researchers are exploring greener alternatives and safer synthetic routes to mitigate potential hazards while maximizing the compound's benefits in various applications.

In conclusion, 3-chloromethyl-1,2,4-triazolin-5-one is a versatile compound with significant potential in agrochemistry, medicinal chemistry, and material science. Its discovery marked an important advancement in the field of triazole chemistry, paving the way for innovative applications that address various industrial and societal needs.

References

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DOI: 10.1055/s-0036-1590760

2016. Synthesis of Doravirine. Synfacts, 12(12).
DOI: 10.1055/s-0036-1589295