4-Iodo-2-nitroaniline CAS 20691-72-9

What is 4-Iodo-2-nitroaniline CAS 20691-72-9?

4-Iodo-2-nitroaniline CAS 20691-72-9 emerged in the late 20th century alongside advancements in halogenated aromatics for synthetic versatility. It is typically prepared via selective iodination of 2-nitroaniline using iodine sources like N-iodosuccinimide in acidic media or Sandmeyer-type processes from diazonium precursors, with production scaled up in research labs and fine chemical facilities to meet demands in pharmaceutical and materials development, emphasizing purification techniques to achieve high purity grades above 98% for downstream applications.

Specification

Feature

• Flexible Referencing: Designated with synonyms such as 4-iodo-2-nitrophenylamine and 2-amino-5-iodonitrobenzene, allowing flexible referencing in chemical databases and facilitating procurement under standardized nomenclature in global supply chains.
• Catalog Integration: Classified under MDL number MFCD06808526 for cataloging, enabling easy integration into computational screening tools for drug design and synthetic route planning in cheminformatics workflows.
• Krohnke Pyridine Synthesis: Serves as a building block in named reactions like the Krohnke pyridine synthesis, where it participates as a halo-substituted aniline to form nitrogen heterocycles through condensation with α,β-unsaturated ketones.
• Friedländer Quinoline Synthesis: Supports the Friedländer quinoline synthesis by acting as an o-amino carbonyl equivalent after nitro reduction, promoting cyclization with aldehydes or ketones to yield fused ring systems in alkaloid analogs.
• Feist-Benary Furan Synthesis: Enables the Feist-Benary furan synthesis as a 2-halo ketone precursor following derivatization, contributing to the assembly of oxygen heterocycles via reaction with 1,3-diketones under basic conditions.
• Custom Synthesis Compatibility: Compatible with custom synthesis services from suppliers like BOC Sciences and TRC, offering scalability from milligram research quantities to kilogram batches while adhering to cGMP standards for pharmaceutical-grade intermediates.

Application

• Organic Synthesis and Heterocycle Formation: Utilized in multi-component reactions such as the Krohnke, Friedländer, and Feist-Benary syntheses to construct pyridines, quinolines, and furans, which serve as core scaffolds in natural product mimics and functional materials like luminescent probes.
• Dye and Pigment Intermediate: Employed in the production of specialty azo dyes and chromophoric compounds, where the iodo group allows for late-stage modifications via Suzuki or Heck couplings to tune color properties for textile and ink formulations.
• Pharmaceutical Development: Acts as a precursor for active pharmaceutical ingredients, including potential antimicrobial agents and enzyme inhibitors, through selective reduction of the nitro group followed by amide bond formation or palladium-catalyzed cross-couplings to build drug-like libraries.
• Agrochemical Synthesis: Integrated into the creation of herbicide and pesticide analogs, leveraging its halogenated structure for introducing aryl substituents in pyrazole or triazole-based active moieties that enhance soil stability and target specificity.
• Materials Science Research: Applied in the design of conjugated polymers and organic semiconductors, where Sonogashira coupling of the iodo functionality links it to alkyne units, yielding materials for OLEDs and photovoltaic devices with improved charge transport.
• Analytical and Biochemical Assays: Incorporated into fluorescent labeling reagents after nitro conversion to amine handles, enabling tracking of biomolecules in high-throughput screening assays for drug discovery and proteomics studies.

Packaging

Mikem offers flexible packaging options, including 25 kg of fiber drums for liquid products and 15–25 kg PP/PE bags for powder products, all customizable to meet your specific needs.