Ethyl 2-amino-4-methylthiazole-5-carboxylate
[CAS# 7210-76-6]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Thiazole, thiophene and pyridine
• Name: Ethyl 2-amino-4-methylthiazole-5-carboxylate
• Synonyms: Ethyl 2-amino-4-methyl-1,3-thiazole-5-carboxylate
• Molecular Formula: C₇H₁₀N₂O₂S
• Molecular Weight: 186.23
• CAS Registry Number: 7210-76-6
• EC Number: 628-116-2
• SMILES: CCOC(=O)C1=C(N=C(S1)N)C

Properties

• Melting point: 177-178 °C
• Water solubility: insoluble

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
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Ethyl 2-amino-4-methylthiazole-5-carboxylate is an organic compound with the molecular formula C7H10N2O2S. It belongs to the thiazole family, characterized by a five-membered ring containing both sulfur and nitrogen atoms. The compound features an amino group at the 2-position, a methyl group at the 4-position, and a carboxylate ester group at the 5-position, making it a versatile molecule in synthetic chemistry and pharmaceutical development.

The discovery of Ethyl 2-amino-4-methylthiazole-5-carboxylate is part of the broader exploration of thiazole derivatives, which have been of interest due to their diverse biological activities and potential applications in drug development. Thiazole rings are commonly found in natural products and synthetic pharmaceuticals, and their derivatives often exhibit antimicrobial, anti-inflammatory, and anticancer properties. The introduction of functional groups like amino and ester into the thiazole ring further enhances the compound’s chemical reactivity and biological activity.

One of the primary applications of Ethyl 2-amino-4-methylthiazole-5-carboxylate is in medicinal chemistry. This compound is used as a building block in the synthesis of various pharmaceutical agents. The presence of the amino group allows for the formation of amide bonds, which are crucial in the design of peptide-like drugs or in modifying existing drug molecules to enhance their activity or bioavailability. The ester group provides a site for further chemical modification, such as hydrolysis to yield the corresponding carboxylic acid, which can then be utilized in drug development.

In addition to its role in drug synthesis, Ethyl 2-amino-4-methylthiazole-5-carboxylate is also used in the development of agrochemicals. The compound's structure allows it to be modified into derivatives that may act as herbicides, insecticides, or fungicides. Thiazole derivatives are known to interfere with specific biological pathways in pests and pathogens, making them effective agents in protecting crops and improving agricultural yields.

The compound is also valuable in the field of organic synthesis, where it serves as a starting material for the creation of more complex molecules. Its functional groups make it suitable for a variety of chemical reactions, including nucleophilic substitutions, condensations, and cyclizations. These reactions can lead to the development of new heterocyclic compounds with potential applications in pharmaceuticals, materials science, and other industries.

Moreover, Ethyl 2-amino-4-methylthiazole-5-carboxylate has been explored for its potential in the development of dyes and pigments. The thiazole ring system can interact with light in specific ways, and when combined with other aromatic systems, it can produce compounds with desirable optical properties. These properties make such derivatives useful in the textile and printing industries, where color stability and intensity are important.

Furthermore, the compound has been studied for its potential use in the development of diagnostic agents. The thiazole ring's ability to form stable complexes with metal ions makes it a candidate for use in imaging techniques or as a precursor in the synthesis of contrast agents used in medical diagnostics.

In summary, Ethyl 2-amino-4-methylthiazole-5-carboxylate is a significant compound in both synthetic and applied chemistry. Its discovery and subsequent applications have led to advancements in pharmaceuticals, agriculture, and materials science. The unique combination of functional groups on the thiazole ring provides the compound with versatile reactivity, making it a valuable tool in the development of new chemical entities and technologies.

References

2024. Design, Synthesis, Molecular Docking, Drug-Likeness/ADMET and Molecular Dynamics Studies of Thiazolyl Benzenesulfonamide Carboxylates as Antimalarial Agents. Chemistry Africa, 7(4).
DOI: 10.1007/s42250-024-00904-7

2021. 1-Methylimidazolium ionic liquid supported on Ni@zeolite-Y: fabrication and performance as a novel multi-functional nanocatalyst for one-pot synthesis of 2-aminothiazoles and 2-aryl benzimidazoles. Research on Chemical Intermediates, 48(1).
DOI: 10.1007/s11164-021-04630-4

2018. One-Pot Telescoped Synthesis of Thiazole Derivatives from β-Keto Esters and Thioureas Promoted by Tribromoisocyanuric Acid. Synthesis, 50(24).
DOI: 10.1055/s-0037-1610243