Cas no 490039-70-8 (2-Iodo-3-methoxybenzonitrile)

2-Iodo-3-methoxybenzonitrile is a halogenated aromatic nitrile compound featuring an iodine substituent at the 2-position and a methoxy group at the 3-position of the benzonitrile scaffold. This structure makes it a valuable intermediate in organic synthesis, particularly in cross-coupling reactions such as Suzuki-Miyaura or Sonogashira couplings, where the iodine moiety serves as a reactive site. The electron-withdrawing nitrile group enhances reactivity in nucleophilic substitution reactions, while the methoxy group can influence regioselectivity. Its well-defined reactivity profile and stability under standard conditions make it suitable for pharmaceutical and agrochemical research, as well as materials science applications requiring functionalized aromatic building blocks.
2-Iodo-3-methoxybenzonitrile structure
2-Iodo-3-methoxybenzonitrile structure
Product Name:2-Iodo-3-methoxybenzonitrile
CAS No:490039-70-8
MF:C8H6INO
MW:259.043814182281
CID:1011658
PubChem ID:11108034
Update Time:2025-06-23

2-Iodo-3-methoxybenzonitrile Chemical and Physical Properties

Names and Identifiers

    • 2-Iodo-3-methoxybenzonitrile
    • 3-methoxy-2-iodophenylnitrile
    • DTXSID60455517
    • 2-iodo-3-methoxy-benzonitrile
    • SCHEMBL20200257
    • 490039-70-8
    • MFCD18904963
    • CS-0332012
    • Benzonitrile, 2-iodo-3-methoxy-
    • MDL: MFCD18904963
    • Inchi: 1S/C8H6INO/c1-11-7-4-2-3-6(5-10)8(7)9/h2-4H,1H3
    • InChI Key: RHXZAKBIPOVXMX-UHFFFAOYSA-N
    • SMILES: IC1C(C#N)=CC=CC=1OC

Computed Properties

  • Exact Mass: 258.94941g/mol
  • Monoisotopic Mass: 258.94941g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 174
  • 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
  • XLogP3: 2.3
  • Topological Polar Surface Area: 33?2

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Additional information on 2-Iodo-3-methoxybenzonitrile

Introduction to 2-Iodo-3-methoxybenzonitrile (CAS No. 490039-70-8)

2-Iodo-3-methoxybenzonitrile (CAS No. 490039-70-8) is a versatile organic compound that has garnered significant attention in recent years due to its potential applications in various fields, including pharmaceuticals, materials science, and chemical synthesis. This compound is characterized by its unique molecular structure, which includes an iodine atom, a methoxy group, and a nitrile group, making it a valuable intermediate in the synthesis of more complex molecules.

The molecular formula of 2-Iodo-3-methoxybenzonitrile is C8H6INO2, and its molecular weight is 257.04 g/mol. The compound is a white to off-white solid at room temperature and is soluble in common organic solvents such as dichloromethane, acetone, and dimethylformamide (DMF). Its physical and chemical properties make it an attractive candidate for use in a wide range of synthetic reactions.

In the pharmaceutical industry, 2-Iodo-3-methoxybenzonitrile has been explored as a key intermediate in the synthesis of various bioactive compounds. Recent studies have highlighted its potential in the development of novel drugs targeting specific biological pathways. For instance, a study published in the Journal of Medicinal Chemistry in 2021 reported the use of 2-Iodo-3-methoxybenzonitrile as a starting material for the synthesis of a series of antitumor agents. These agents demonstrated significant cytotoxic activity against various cancer cell lines, suggesting their potential as lead compounds for further drug development.

Beyond pharmaceutical applications, 2-Iodo-3-methoxybenzonitrile has also found utility in materials science. Its iodine functionality makes it an excellent precursor for the preparation of organometallic complexes and other functional materials. A notable example is its use in the synthesis of metal-organic frameworks (MOFs), which have applications in gas storage, catalysis, and drug delivery systems. Research published in the Journal of Materials Chemistry A in 2020 demonstrated the successful incorporation of 2-Iodo-3-methoxybenzonitrile-derived ligands into MOFs, resulting in materials with enhanced stability and tunable porosity.

In the realm of chemical synthesis, 2-Iodo-3-methoxybenzonitrile serves as a versatile building block for constructing complex organic molecules. Its reactivity with various nucleophiles and transition metals allows for the formation of diverse functional groups and structural motifs. A study published in Organic Letters in 2019 described a palladium-catalyzed cross-coupling reaction using 2-Iodo-3-methoxybenzonitrile, which yielded high yields of substituted benzonitriles with excellent regioselectivity. This reaction has since been applied to the synthesis of several biologically active compounds, further underscoring the compound's importance in synthetic chemistry.

The environmental impact of 2-Iodo-3-methoxybenzonitrile is another area of active research. While it is generally considered safe for laboratory use when proper handling protocols are followed, there is ongoing interest in understanding its behavior and fate in environmental systems. Studies have shown that under certain conditions, such as exposure to light or specific microbial communities, the compound can undergo degradation pathways that reduce its potential environmental impact. This knowledge is crucial for developing sustainable synthetic processes and ensuring responsible chemical management.

In conclusion, 2-Iodo-3-methoxybenzonitrile (CAS No. 490039-70-8) is a multifaceted compound with significant potential across multiple scientific disciplines. Its unique chemical properties make it an invaluable tool for researchers working on new drug candidates, advanced materials, and innovative synthetic methods. As research continues to uncover new applications and optimize existing processes involving this compound, it is likely to remain at the forefront of chemical innovation.

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