2-(Isopropylamino)-1,3-thiazole-4-carboxylic acid: Properties & Lab Guide
2-(Isopropylamino)-1,3-thiazole-4-carboxylic acid: Properties & Lab Guide
2-(Isopropylamino)-1,3-thiazole-4-carboxylic acid is a functionalized aminothiazole heterocyclic compound widely employed as a synthetic building block in medicinal chemistry and drug discovery programs.
- Chemical Name
- 2-(Isopropylamino)-1,3-thiazole-4-carboxylic acid
- SKU
- T726373
- Core Scaffold
- 1,3-Thiazole ring with isopropylamino substituent at C-2 and carboxylic acid at C-4
- Functional Groups
- Secondary amine (isopropylamino), carboxylic acid, aromatic thiazole
- Primary Application
- Synthetic intermediate and building block for heterocyclic compound libraries
- Storage Recommendation
- Store in a cool, dry, well-ventilated location away from incompatible materials
Chemical Structure and Key Properties
2-(Isopropylamino)-1,3-thiazole-4-carboxylic acid (Aladdin SKU: T726373) is a thiazole-based heterocyclic compound. The molecule features a five-membered 1,3-thiazole aromatic ring bearing two key substituents: an isopropylamino (secondary amine) group at the C-2 position and a carboxylic acid group at the C-4 position. This bifunctional architecture makes the compound a versatile scaffold in synthetic organic and medicinal chemistry.
The isopropylamino group at C-2 donates electron density into the thiazole ring through resonance, influencing the electronic character of the heterocycle and enhancing its capacity to participate in hydrogen-bonding interactions. The carboxylic acid at C-4 provides a reactive handle for amide bond formation, esterification, and other coupling reactions, making the compound highly amenable to downstream derivatization.
The compound is expected to be a solid at room temperature, consistent with typical aminothiazole carboxylic acids of similar molecular weight. Precise physicochemical data including melting point, solubility profile, and pKa values should be confirmed from the certificate of analysis (CoA) supplied with each lot.
Handling, Safety, and Storage Guidelines
As with all fine chemical reagents containing amine and carboxylic acid functionalities, appropriate laboratory safety practices must be followed when handling 2-(Isopropylamino)-1,3-thiazole-4-carboxylic acid. Personnel should wear appropriate personal protective equipment (PPE), including chemical-resistant gloves, laboratory coat, and eye protection, to minimize dermal and ocular exposure.
The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated area, away from strong oxidizing agents and strong bases or acids that could react with the carboxylic acid or amine functionalities. Exposure to moisture should be minimized to preserve reagent integrity over time.
In the event of skin or eye contact, immediately flush with large amounts of water and seek medical advice if irritation persists. Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for comprehensive hazard information, first-aid measures, and disposal guidance before use. Specific GHS hazard classifications and pictograms should be verified from the product SDS.
Research and Synthetic Applications
Aminothiazole carboxylic acids represent an important class of heterocyclic building blocks in medicinal chemistry, combinatorial chemistry, and pharmaceutical research. The 2-aminothiazole motif is a privileged scaffold found in a broad range of biologically active compounds and approved drugs, valued for its ability to engage in hydrogen-bond donor and acceptor interactions with biological targets.
2-(Isopropylamino)-1,3-thiazole-4-carboxylic acid is particularly useful as a synthetic intermediate for the construction of amide libraries via coupling with amines using standard peptide coupling reagents (e.g., HATU, EDC/HOBt, or T3P). The carboxylic acid can also be converted to acid chlorides, mixed anhydrides, or activated esters to enable further diversification. The isopropylamino group itself may serve as a handle for additional functionalization or may contribute to the pharmacophore in a target molecule.
Potential research applications include: (1) fragment-based drug discovery (FBDD) as a thiazole fragment; (2) construction of kinase inhibitor scaffolds; (3) preparation of fluorescent probes or metal-chelating ligands incorporating the thiazole unit; and (4) use as a reference standard in analytical method development. Researchers are encouraged to consult the primary literature for specific application protocols relevant to their target biological systems.
Quality, Purity, and Ordering Information
Aladdin Scientific supplies 2-(Isopropylamino)-1,3-thiazole-4-carboxylic acid under SKU T726373. Each lot is accompanied by a Certificate of Analysis (CoA) documenting identity confirmation (typically by NMR and/or MS), purity (typically assessed by HPLC), and appearance. Researchers should request or download the relevant CoA for their specific lot to verify that the material meets the specifications required for their application.
For applications requiring the highest level of confidence in structural identity and purity—such as biological assays, reference standard preparation, or regulatory submissions—researchers should review the CoA carefully and may wish to perform independent analytical verification (e.g., LC-MS, ¹H NMR) upon receipt.
To order, visit the Aladdin Scientific website and search by product name or SKU T726373. For bulk quantities, custom packaging, or additional technical support, contact the Aladdin Scientific sales and technical service team directly. Pricing and availability are subject to change; consult the website or contact customer service for current information.
Frequently asked questions
What is the recommended solvent for dissolving 2-(Isopropylamino)-1,3-thiazole-4-carboxylic acid?
Aminothiazole carboxylic acids of this type are generally soluble in polar aprotic solvents such as DMSO and DMF, and may also dissolve in dilute aqueous base (e.g., dilute NaOH or sodium bicarbonate solution) due to the ionizable carboxylic acid group. Solubility in aqueous buffers at neutral pH is typically limited. Researchers should confirm solubility empirically for their specific application and consult the CoA or SDS for additional guidance.
Can the carboxylic acid group of this compound be used directly in amide coupling reactions?
Yes. The carboxylic acid at C-4 of the thiazole ring is well-suited for standard amide bond-forming reactions using common coupling reagents such as HATU, EDC/HOBt, DCC/HOBt, or T3P in the presence of a suitable base. The isopropylamino group at C-2 is a secondary amine and is generally less reactive under standard coupling conditions, but researchers should consider potential competing side reactions and optimize conditions accordingly.
How should I verify the identity and purity of the received material?
Identity can be confirmed by comparing the ¹H NMR spectrum and/or high-resolution mass spectrum of the received material against the molecular formula and expected chemical shifts for the compound. Purity is most reliably assessed by reverse-phase HPLC with UV detection. The Certificate of Analysis (CoA) provided by Aladdin Scientific with each lot documents the analytical results obtained during quality control and should be reviewed upon receipt.
What is the shelf life of 2-(Isopropylamino)-1,3-thiazole-4-carboxylic acid?
Shelf life information is lot-specific and is stated on the product label and Certificate of Analysis. In general, heterocyclic carboxylic acid building blocks stored under recommended conditions (cool, dry, sealed, away from light and moisture) remain stable for an extended period. Researchers should verify the expiry date on the CoA and re-analyze the material if there is any doubt about its integrity after prolonged storage.
References
- Aladdin Scientific product page for 2-(Isopropylamino)-1,3-thiazole-4-carboxylic acid, SKU T726373.
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for amide bond-forming reactions and heterocyclic chemistry.
- Joule, J. A.; Mills, K. Heterocyclic Chemistry. Blackwell Publishing. Standard reference for the chemistry and reactivity of thiazole ring systems.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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