5-(2-Thiazolyl)isoxazole-3-carboxylic Acid: Properties & Uses
5-(2-Thiazolyl)isoxazole-3-carboxylic Acid: Properties & Uses
5-(2-Thiazolyl)isoxazole-3-carboxylic Acid is a bifunctional heterocyclic compound combining an isoxazole core with a thiazolyl substituent and a carboxylic acid handle, making it a versatile building block for medicinal chemistry and synthetic research.
- Chemical Name
- 5-(2-Thiazolyl)isoxazole-3-carboxylic Acid
- SKU
- I691780
- Core Heterocycles
- Isoxazole and Thiazole
- Key Functional Group
- Carboxylic acid (-COOH) at position 3 of the isoxazole ring
- Primary Application
- Heterocyclic building block for medicinal chemistry and material science research
- Supplier
- Aladdin Scientific
Chemical Structure and Properties
5-(2-Thiazolyl)isoxazole-3-carboxylic Acid is a heteroaromatic compound featuring two distinct aromatic nitrogen-containing rings. The isoxazole ring, a five-membered ring containing both oxygen and nitrogen, is substituted at the 5-position by a 2-thiazolyl group—itself a sulfur- and nitrogen-containing five-membered aromatic ring—and bears a carboxylic acid group at the 3-position.
This combination of pharmacophoric elements endows the molecule with a rich hydrogen-bond donor and acceptor profile. The carboxylic acid moiety (-COOH) provides an acidic proton and acts as a handle for amide coupling, esterification, and other classic carboxylic acid transformations. The heteroaromatic system contributes π-stacking capability and coordination potential toward metal centers, properties valued in both drug discovery and materials science contexts.
Synthesis and Reactivity
Isoxazole-3-carboxylic acid derivatives are commonly prepared via [3+2] cycloaddition strategies, wherein nitrile oxides—generated in situ from hydroxamoyl chlorides or aldoximes—react with appropriate dipolarophiles. The incorporation of a thiazolyl group at the 5-position may be achieved by selecting a 2-thiazolyl-substituted alkyne or enone as the dipolarophile, or through post-cyclization cross-coupling methodologies.
The carboxylic acid group at the 3-position is highly reactive and readily participates in standard transformations: amide bond formation using coupling reagents such as EDC or HATU, esterification under acidic or carbodiimide-mediated conditions, and conversion to acyl halides or mixed anhydrides for further elaboration. These properties make 5-(2-Thiazolyl)isoxazole-3-carboxylic Acid a practical synthetic intermediate for constructing more complex heterocyclic architectures.
Research and Medicinal Chemistry Applications
Compounds bearing isoxazole and thiazole rings are well represented in bioactive molecules and approved pharmaceuticals. Both ring systems are recognized bioisosteres of amide bonds and carboxylic acids, contributing to metabolic stability and favorable pharmacokinetic profiles. As a bifunctional building block, 5-(2-Thiazolyl)isoxazole-3-carboxylic Acid is of interest in fragment-based drug discovery, where compact heteroaromatic fragments are screened and elaborated into lead compounds.
In addition to pharmaceutical research, the coordination chemistry of bis-heterocyclic systems is exploited in the design of metal-organic frameworks (MOFs) and coordination polymers. The dual nitrogen-donor capacity of the thiazolyl-isoxazole scaffold, combined with the carboxylate group present under basic conditions, supports chelation to transition metals and the assembly of supramolecular structures with potential applications in catalysis and sensing.
Handling, Storage, and Safety Considerations
As with most research-grade heteroaromatic carboxylic acids, 5-(2-Thiazolyl)isoxazole-3-carboxylic Acid should be handled with standard laboratory precautions. Personnel should wear appropriate personal protective equipment including gloves, safety glasses, and a lab coat. The compound should be handled in a well-ventilated area or fume hood to minimize inhalation exposure to dust or aerosols.
For storage, the material should be kept in a tightly sealed container under cool, dry conditions, away from strong oxidizing agents and bases that could react with the carboxylic acid functionality or degrade the heteroaromatic rings. Refer to the product-specific Safety Data Sheet (SDS) supplied by Aladdin Scientific for detailed hazard classifications, first-aid measures, and disposal guidance.
Frequently asked questions
What is 5-(2-Thiazolyl)isoxazole-3-carboxylic Acid used for in research?
It is primarily used as a heterocyclic building block in medicinal chemistry for the synthesis of more complex drug-like molecules. Its reactive carboxylic acid group enables amide coupling and esterification, while the bis-heteroaromatic scaffold is valuable in fragment-based drug discovery and coordination chemistry research.
How should 5-(2-Thiazolyl)isoxazole-3-carboxylic Acid be stored?
The compound should be stored in a tightly sealed container under cool, dry conditions, away from strong oxidizing agents and bases. Always consult the product Safety Data Sheet (SDS) from Aladdin Scientific for specific storage recommendations.
What reactions can the carboxylic acid group of this compound undergo?
The carboxylic acid at the 3-position of the isoxazole ring can undergo amide bond formation using standard coupling reagents (e.g., EDC, HATU), esterification under acidic or carbodiimide-mediated conditions, and conversion to acyl chlorides or mixed anhydrides, enabling diverse synthetic elaborations.
Is 5-(2-Thiazolyl)isoxazole-3-carboxylic Acid suitable for metal coordination chemistry?
Yes. The compound's thiazolyl and isoxazole nitrogen atoms provide multiple donor sites for transition metal coordination, and the carboxylate group under basic conditions further supports chelation. This makes it a candidate ligand for the construction of metal-organic frameworks and coordination polymers.
References
- Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed.; Wiley-Blackwell: Oxford, 2010. (General reference on isoxazole and thiazole chemistry.)
- Aladdin Scientific Product Page. 5-(2-Thiazolyl)isoxazole-3-carboxylic Acid, SKU I691780.
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