Cas no 197243-48-4 (2-Iodo-3-nitrophenol)

2-Iodo-3-nitrophenol is a halogenated nitrophenol compound with the molecular formula C?H?INO?. This yellow to light brown crystalline solid is primarily utilized as an intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. Its distinct molecular structure, featuring both iodine and nitro functional groups, enables selective reactivity in cross-coupling reactions and electrophilic substitutions. The compound exhibits moderate solubility in organic solvents, facilitating its use in controlled synthetic processes. Due to its stability under standard conditions and well-characterized reactivity, 2-Iodo-3-nitrophenol is valued for its role in constructing complex aromatic frameworks in research and industrial applications. Proper handling is advised due to potential irritant properties.
2-Iodo-3-nitrophenol structure
2-Iodo-3-nitrophenol structure
Product Name:2-Iodo-3-nitrophenol
CAS No:197243-48-4
MF:C6H4INO3
MW:265.005333900452
MDL:MFCD06797891
CID:117073
PubChem ID:12167350
Update Time:2025-10-07

2-Iodo-3-nitrophenol Chemical and Physical Properties

Names and Identifiers

    • Phenol, 2-iodo-3-nitro-
    • 2-iodo-3-nitrophenol
    • SCHEMBL3677999
    • DTXSID40479039
    • AC-30072
    • SY060719
    • 197243-48-4
    • nitroiodophenol
    • EN300-175100
    • A925131
    • AC1618
    • CS-12550
    • AKOS027323054
    • MFCD06797891
    • BFXOSMOZBIBXHU-UHFFFAOYSA-N
    • STL450355
    • DB-182286
    • 2-Iodo-3-nitrophenol
    • MDL: MFCD06797891
    • Inchi: 1S/C6H4INO3/c7-6-4(8(10)11)2-1-3-5(6)9/h1-3,9H
    • InChI Key: BFXOSMOZBIBXHU-UHFFFAOYSA-N
    • SMILES: IC1C(=CC=CC=1[N+](=O)[O-])O

Computed Properties

  • Exact Mass: 264.92312
  • Monoisotopic Mass: 264.92359g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 158
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 66?2
  • Surface Charge: 0
  • Tautomer Count: 3
  • XLogP3: 2

Experimental Properties

  • Density: 2.176±0.06 g/cm3 (20 oC 760 Torr),
  • Melting Point: 134 oC
  • Boiling Point: 271.2±30.0 oC (760 Torr),
  • Flash Point: 117.8±24.6 oC,
  • Solubility: Very slightly soluble (0.9 g/l) (25 o C),
  • PSA: 63.37

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2-Iodo-3-nitrophenol Related Literature

Additional information on 2-Iodo-3-nitrophenol

Research Briefing on 2-Iodo-3-nitrophenol (CAS: 197243-48-4) in Chemical Biology and Pharmaceutical Applications

2-Iodo-3-nitrophenol (CAS: 197243-48-4) is a halogenated nitrophenol derivative that has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound serves as a crucial intermediate in the synthesis of various bioactive molecules, including potential drug candidates and diagnostic agents. Recent studies have explored its utility in cross-coupling reactions, medicinal chemistry, and materials science, highlighting its broad applicability.

In the context of pharmaceutical research, 2-Iodo-3-nitrophenol has been investigated for its role in the development of novel antimicrobial and anticancer agents. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its efficacy as a building block for the synthesis of iodinated quinoline derivatives, which exhibited potent activity against multidrug-resistant bacterial strains. The study emphasized the compound's unique reactivity, attributed to the synergistic effects of the iodine and nitro functional groups.

From a chemical biology perspective, 2-Iodo-3-nitrophenol has been utilized as a probe to study enzyme mechanisms and protein-ligand interactions. A recent preprint on bioRxiv detailed its use in photoaffinity labeling experiments, where it served as a photoactivatable crosslinker to map binding sites in target proteins. This application underscores its potential in elucidating molecular pathways and identifying new therapeutic targets.

Advancements in synthetic methodologies have also been reported, with a focus on improving the yield and purity of 2-Iodo-3-nitrophenol. A 2024 publication in Organic Process Research & Development described a scalable, green chemistry approach using catalytic iodination, reducing the environmental impact of its production. These innovations are critical for meeting the growing demand for high-quality intermediates in drug discovery pipelines.

In conclusion, 2-Iodo-3-nitrophenol (CAS: 197243-48-4) continues to be a valuable tool in both academic and industrial research settings. Its multifaceted applications—from drug development to chemical biology—highlight its importance in advancing scientific knowledge and therapeutic innovation. Future research directions may include exploring its potential in nanotechnology and targeted drug delivery systems, further expanding its utility in the life sciences.

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