What Is Ethyl 3-Iodo-1H-Indole-2-Carboxylate?

Ethyl 3-iodo-1H-indole-2-carboxylate (SKU: E725161) is a synthetic organic compound belonging to the indole family of heterocycles. Its structure consists of a bicyclic indole core functionalized with an iodine atom at the C-3 position and an ethyl ester group at the C-2 position. The molecular formula is C₁₁H₁₀INO₂, giving a molecular weight of approximately 315.11 g/mol.

The C-3 iodo group renders this compound highly reactive toward metal-catalyzed cross-coupling reactions (e.g., Suzuki, Sonogashira, Negishi, and Heck couplings), while the ethyl ester at C-2 provides an additional handle for further chemical elaboration, including hydrolysis, amidation, and reduction. The free NH of the indole nitrogen is also available for N-functionalization under appropriate conditions.

Key Applications in Organic Synthesis

The combination of a reactive C–I bond and an electron-withdrawing ester group makes Ethyl 3-iodo-1H-indole-2-carboxylate a particularly valuable intermediate in pharmaceutical and agrochemical research. Common applications include:

• Palladium-catalyzed cross-coupling: The C-3 iodo group undergoes efficient Suzuki–Miyaura, Sonogashira, and Negishi couplings, allowing introduction of aryl, heteroaryl, vinyl, or alkynyl groups at C-3.
• Directed metalation and further functionalization: The ester group can direct ortholithiation or serve as a precursor to carboxylic acids, amides, aldehydes, and alcohols.
• Synthesis of complex indole alkaloids and drug scaffolds: The 2,3-disubstituted indole framework is present in many biologically active natural products and pharmaceuticals.
• Radical reactions: The C–I bond can participate in radical-mediated cyclization and addition reactions.

Researchers in medicinal chemistry, total synthesis, and material science routinely employ this compound as a starting material or advanced intermediate.

Handling, Safety, and Storage Guidelines

As with all laboratory reagents, Ethyl 3-iodo-1H-indole-2-carboxylate should be handled with appropriate precautions:

• Personal protective equipment: Wear nitrile gloves, safety glasses, and a laboratory coat when handling this compound. Use in a fume hood to avoid inhalation of dust or vapors.
• Storage: Store in a tightly sealed container in a cool, dry, and well-ventilated area away from direct light and incompatible materials (strong oxidizers, strong bases). Specific recommended storage temperature should be verified against the current Safety Data Sheet (SDS) for SKU E725161.
• Stability: The C–I bond in aryl iodides is generally stable under ambient storage conditions but may be sensitive to prolonged exposure to light or moisture. Users should confirm stability data from the product SDS.
• Disposal: Dispose of waste in accordance with local, regional, and national regulations for halogenated organic compounds.

Always consult the current SDS provided by Aladdin Scientific before use.

Ordering, Purity, and Specifications

Ethyl 3-iodo-1H-indole-2-carboxylate is available from Aladdin Scientific under SKU E725161. When placing an order, researchers and procurement staff should note the following:

• Purity: The purity grade and exact specification (e.g., ≥95% or ≥97% by HPLC or GC) should be confirmed on the current product page or by contacting Aladdin customer service, as these details were not specified in the source material.
• Available quantities: Pack sizes and available quantities should be verified on the Aladdin Scientific website or through your regional distributor.
• Certificate of Analysis (CoA): A CoA documenting purity, appearance, and analytical data is available upon request for each lot.
• Lead time: Standard stock availability and lead times vary; contact Aladdin Scientific sales or check the product listing for current stock status.

For bulk quantities, custom synthesis inquiries, or special purity requirements, please contact Aladdin Scientific directly.

Quality Assurance and Analytical Characterization

Aladdin Scientific ensures reagent quality through standard analytical characterization of each production lot. For Ethyl 3-iodo-1H-indole-2-carboxylate (E725161), characterization typically includes:

• Chromatographic purity: HPLC or GC analysis to confirm purity of the bulk material.
• Structural confirmation: NMR spectroscopy (¹H and ¹³C) and/or mass spectrometry to confirm molecular identity.
• Physical appearance: Visual inspection for color and physical state consistency (specific appearance data should be confirmed from the product CoA).

Researchers requiring additional analytical data or custom testing should contact Aladdin Scientific technical support. All lot-specific analytical data are documented on the Certificate of Analysis available per batch.