Cas no 885521-22-2 (3-iodo-4-nitro-1H-indazole)

3-Iodo-4-nitro-1H-indazole is a heterocyclic organic compound featuring an indazole core substituted with iodine at the 3-position and a nitro group at the 4-position. This structure imparts unique reactivity, making it a valuable intermediate in pharmaceutical and agrochemical synthesis. The iodine moiety offers versatility for further functionalization via cross-coupling reactions, while the nitro group enhances electrophilic properties, facilitating nucleophilic substitution or reduction to amines. Its high purity and stability under standard conditions ensure reliable performance in research and industrial applications. This compound is particularly useful in the development of bioactive molecules, serving as a key building block for targeted drug discovery and material science innovations.
3-iodo-4-nitro-1H-indazole structure
3-iodo-4-nitro-1H-indazole structure
Product Name:3-iodo-4-nitro-1H-indazole
CAS No:885521-22-2
MF:C7H4IN3O2
MW:289.030033111572
MDL:MFCD07781574
CID:720080
PubChem ID:24728193
Update Time:2025-05-25

3-iodo-4-nitro-1H-indazole Chemical and Physical Properties

Names and Identifiers

    • 1H-Indazole,3-iodo-4-nitro-
    • 3-Iodo-4-nitro (1H)indazole
    • 3-iodo-4-nitro-1H-indazole
    • 3-iodo-4-nitro-2H-indazole
    • NULL
    • 3-iodanyl-4-nitro-2H-indazole
    • iodonitroindazole
    • 3-Iodo-4-nitro-1H-indazole (ACI)
    • AOTAXYVEONHYHY-UHFFFAOYSA-N
    • DTXSID10646251
    • AKOS005072415
    • CS-0051310
    • 3-Iodo-4-nitro(1H)indazole
    • DB-077964
    • J-512683
    • SCHEMBL1172817
    • PB26282
    • EN300-303669
    • MFCD07781574
    • 885521-22-2
    • ED-0749
    • MDL: MFCD07781574
    • Inchi: 1S/C7H4IN3O2/c8-7-6-4(9-10-7)2-1-3-5(6)11(12)13/h1-3H,(H,9,10)
    • InChI Key: AOTAXYVEONHYHY-UHFFFAOYSA-N
    • SMILES: [O-][N+](C1C2=C(NN=C2I)C=CC=1)=O

Computed Properties

  • Exact Mass: 288.93500
  • Monoisotopic Mass: 288.935
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 220
  • 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: 74.5A^2
  • XLogP3: 2.1

Experimental Properties

  • Melting Point: 210-212°
  • Refractive Index: 1.818
  • PSA: 74.50000
  • LogP: 2.59890

3-iodo-4-nitro-1H-indazole Security Information

  • HazardClass:IRRITANT

3-iodo-4-nitro-1H-indazole Customs Data

  • HS CODE:2933990090
  • Customs Data:

    China Customs Code:

    2933990090

    Overview:

    2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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3-iodo-4-nitro-1H-indazole Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Potassium hydroxide Solvents: Dimethylformamide ;  4 d, rt
Reference
Identification of 3-sulfonylindazole derivatives as potent and selective 5-HT6 antagonists
Liu, Kevin G.; Robichaud, Albert J.; Greenfield, Alexander A.; Lo, Jennifer R.; Grosanu, Cristina; et al, Bioorganic & Medicinal Chemistry, 2011, 19(1), 650-662

3-iodo-4-nitro-1H-indazole Raw materials

3-iodo-4-nitro-1H-indazole Preparation Products

Additional information on 3-iodo-4-nitro-1H-indazole

3-Iodo-4-Nitro-1H-Indazole: A Comprehensive Overview

3-Iodo-4-nitro-1H-indazole (CAS No. 885521-22-2) is a heterocyclic aromatic compound that has garnered significant attention in the fields of organic chemistry, pharmacology, and materials science. This compound belongs to the indazole family, which is a bicyclic structure consisting of a benzene ring fused with an imidazole ring. The presence of an iodine atom at the 3-position and a nitro group at the 4-position imparts unique electronic and structural properties to this molecule, making it a valuable compound for various applications.

The synthesis of 3-iodo-4-nitro-1H-indazole typically involves multi-step reactions, often starting from indazole precursors. Recent advancements in synthetic methodologies have focused on optimizing reaction conditions to improve yield and purity. For instance, researchers have explored the use of microwave-assisted synthesis and catalytic systems to streamline the process. These innovations not only enhance the efficiency of production but also pave the way for large-scale manufacturing, which is crucial for its potential commercial applications.

In terms of pharmacological activity, 3-iodo-4-nitro-1H-indazole has shown promising results in preclinical studies. The nitro group at the 4-position is known to confer strong electron-withdrawing properties, which can influence the compound's interaction with biological systems. Recent studies have demonstrated its potential as an anti-tumor agent, particularly in targeting specific signaling pathways involved in cancer cell proliferation. Additionally, the iodine substituent at the 3-position may play a role in modulating the compound's bioavailability and pharmacokinetics, making it a candidate for drug delivery systems.

The electronic properties of 3-iodo-4-nitro-1H-indazole make it an interesting material for optoelectronic applications. The conjugated system within the indazole framework allows for efficient charge transport, which is essential in devices such as organic light-emitting diodes (OLEDs) and photovoltaic cells. Recent research has highlighted its potential as a hole transport material due to its high conductivity and stability under operational conditions. Furthermore, the substituents' electronic effects can be fine-tuned to optimize performance in these devices.

In conclusion, 3-iodo-4-nitro-1H-indazole (CAS No. 885521-22-2) stands out as a versatile compound with applications spanning multiple disciplines. Its unique structure, combined with recent advancements in synthesis and application development, positions it as a valuable tool in both academic research and industrial settings. As ongoing studies continue to uncover new insights into its properties and functionalities, this compound is poised to make significant contributions to fields ranging from medicine to materials science.

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