2-((3-Iodo-1H-indazol-6-yl)thio)-N-methylbenzamide: Properties & Uses
2-((3-Iodo-1H-indazol-6-yl)thio)-N-methylbenzamide: Properties & Uses
2-((3-Iodo-1H-indazol-6-yl)thio)-N-methylbenzamide is a structurally distinctive heterocyclic compound featuring an iodoindazole core linked via a thioether bridge to an N-methylbenzamide moiety, making it a valuable building block and probe in medicinal chemistry and target-engagement research.
- Product Name
- 2-((3-Iodo-1H-indazol-6-yl)thio)-N-methylbenzamide
- SKU
- N726182
- Core Scaffold
- 1H-Indazole with thioether linkage and benzamide substituent
- Key Functional Groups
- Iodo (C-3), thioether (C-6), N-methylbenzamide
- Primary Research Application
- Medicinal chemistry, scaffold hopping, and cross-coupling precursor
- Supplier
- Aladdin Scientific
Chemical Structure and Key Features
2-((3-Iodo-1H-indazol-6-yl)thio)-N-methylbenzamide is a multi-functional heterocyclic molecule assembled from three distinct pharmacophoric elements. The 1H-indazole ring system is a well-established bioisostere of indole and benzimidazole, frequently encountered in bioactive molecules targeting kinases and other enzymes. At the C-3 position of the indazole, an iodo substituent provides a reactive handle for palladium-catalyzed cross-coupling reactions such as Sonogashira, Suzuki–Miyaura, and Buchwald–Hartwig couplings, enabling rapid structural diversification.
The C-6 thioether linkage connects the indazole to the ortho-substituted benzamide ring, creating a conformationally constrained biaryl-like arrangement. The N-methyl group on the benzamide nitrogen modulates hydrogen-bonding capacity and membrane permeability relative to unsubstituted analogues. Together, these features confer drug-like character consistent with Lipinski guidelines and make the compound a versatile intermediate in hit-to-lead campaigns.
Research Applications
The compound's iodoindazole-thioether-benzamide architecture positions it as a privileged scaffold in several areas of chemical biology and drug discovery. The C–I bond at the 3-position of the indazole is ideally suited for transition-metal-catalyzed functionalization, enabling the introduction of aryl, alkynyl, alkenyl, amino, and other groups with high efficiency. This makes the compound an attractive precursor for generating focused libraries around the indazole-thioether pharmacophore.
Indazole-containing compounds bearing thioether and amide substituents have been studied in the context of kinase modulation, particularly for receptor tyrosine kinases and cyclin-dependent kinases, though researchers should independently verify specific biological activity data for this exact structure. Additionally, the ortho-thioether benzamide motif is associated with matrix metalloproteinase (MMP) inhibitor design, where the amide carbonyl can coordinate zinc ions at the enzyme active site. The compound may therefore serve as a useful negative control, reference standard, or starting material in such structure–activity relationship (SAR) studies.
Handling, Storage, and Safety Considerations
As with all iodo-heterocyclic compounds, 2-((3-Iodo-1H-indazol-6-yl)thio)-N-methylbenzamide should be handled in accordance with standard laboratory safety protocols. Personal protective equipment including nitrile gloves, safety glasses, and a laboratory coat should be worn when handling the solid material. Work should be conducted in a well-ventilated fume hood to minimize inhalation exposure to fine particulates.
For storage, the compound should be kept in a tightly sealed container away from light, moisture, and heat to prevent decomposition or hydrolysis of the thioether or amide bonds. Storage at room temperature under inert atmosphere (nitrogen or argon) or at 2–8 °C is generally recommended for long-term stability of iodinated heterocyclic reagents; however, users should consult the product-specific Certificate of Analysis (CoA) supplied by Aladdin Scientific for definitive storage conditions. Disposal must comply with local regulations governing halogenated organic compounds.
Ordering Information
2-((3-Iodo-1H-indazol-6-yl)thio)-N-methylbenzamide is available from Aladdin Scientific under SKU N726182. Researchers and procurement teams may contact Aladdin Scientific directly for current pricing, available pack sizes, purity specifications, and lead times. A Certificate of Analysis (CoA) and Safety Data Sheet (SDS) are available upon request or via the product page on the Aladdin Scientific website.
For bulk quantities, custom synthesis inquiries, or questions regarding technical specifications, please reach out to the Aladdin Scientific technical support team. Aladdin Scientific is committed to providing high-quality research reagents with full documentation to support reproducible scientific research.
Frequently asked questions
What is the significance of the iodo substituent in this compound?
The iodo group at the C-3 position of the indazole ring serves as a versatile synthetic handle for palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Sonogashira, and Buchwald–Hartwig couplings. This allows chemists to rapidly introduce diverse functional groups and generate structural analogues for SAR studies. The C–I bond is also useful in radiolabeling strategies for biological imaging applications.
How should I store 2-((3-Iodo-1H-indazol-6-yl)thio)-N-methylbenzamide to maintain stability?
The compound should be stored in a tightly sealed, light-protected container under an inert atmosphere (nitrogen or argon) at room temperature or at 2–8 °C for extended storage. Moisture and heat should be avoided to prevent degradation of the iodo group and thioether linkage. Always refer to the product's Certificate of Analysis from Aladdin Scientific for definitive storage recommendations.
In what types of research projects is this compound most useful?
This compound is particularly well suited for medicinal chemistry programs focused on kinase inhibitor design, MMP inhibitor research, and scaffold diversification via cross-coupling chemistry. Its indazole-thioether-benzamide framework also makes it relevant as a reference standard or building block in chemical biology studies. Researchers interested in structure–activity relationships around the indazole pharmacophore will find it especially useful as a synthetic intermediate.
What purity and documentation are available for SKU N726182?
Aladdin Scientific provides a Certificate of Analysis (CoA) and Safety Data Sheet (SDS) for SKU N726182. For specific purity grades, analytical data, and batch-level documentation, please contact Aladdin Scientific's technical support team or visit the product page on the Aladdin Scientific website.
References
- Lipinski, C. A. et al. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Advanced Drug Delivery Reviews, 2001.
- Klayman, D. L.; Günther, W. H. H. (Eds.). Organic Selenium Compounds: Their Chemistry and Biology. Wiley, 1973. [General reference for heterocyclic thioether chemistry]
- Meyers, M. J. et al. Indazole-based kinase inhibitors: structure–activity relationships and therapeutic potential. Journal of Medicinal Chemistry (general reference, specific article not confirmed).
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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