Cas no 1160574-12-8 (3-Bromo-2-fluoro-5-iodobenzonitrile)

3-Bromo-2-fluoro-5-iodobenzonitrile is a halogenated benzonitrile derivative with a unique substitution pattern, making it a valuable intermediate in organic synthesis and pharmaceutical research. The presence of bromo, fluoro, and iodo substituents on the aromatic ring offers multiple sites for further functionalization via cross-coupling reactions, nucleophilic substitutions, or metal-catalyzed transformations. Its electron-withdrawing nitrile group enhances reactivity in heterocycle formation and other condensation reactions. This compound is particularly useful in the development of agrochemicals, liquid crystals, and bioactive molecules due to its structural versatility. High purity grades ensure consistent performance in demanding synthetic applications. Proper handling is required due to potential sensitivity to light and moisture.
3-Bromo-2-fluoro-5-iodobenzonitrile structure
1160574-12-8 structure
Product Name:3-Bromo-2-fluoro-5-iodobenzonitrile
CAS No:1160574-12-8
MF:C7H2BrFIN
MW:325.904356479645
MDL:MFCD11846060
CID:4574260
Update Time:2025-06-10

3-Bromo-2-fluoro-5-iodobenzonitrile Chemical and Physical Properties

Names and Identifiers

    • 3-Bromo-2-fluoro-5-iodobenzonitrile
    • Benzonitrile, 3-bromo-2-fluoro-5-iodo-
    • MDL: MFCD11846060
    • Inchi: 1S/C7H2BrFIN/c8-6-2-5(10)1-4(3-11)7(6)9/h1-2H
    • InChI Key: MNSJLMXWCZEFKV-UHFFFAOYSA-N
    • SMILES: C(#N)C1=CC(I)=CC(Br)=C1F

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0

3-Bromo-2-fluoro-5-iodobenzonitrile Pricemore >>

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Additional information on 3-Bromo-2-fluoro-5-iodobenzonitrile

Introduction to 3-Bromo-2-fluoro-5-iodobenzonitrile (CAS No. 1160574-12-8)

3-Bromo-2-fluoro-5-iodobenzonitrile, identified by the Chemical Abstracts Service Number (CAS No.) 1160574-12-8, is a specialized organic compound that has garnered significant attention in the field of medicinal chemistry and synthetic organic chemistry. This compound belongs to the class of halogenated benzonitriles, a subgroup known for its versatile applications in the development of pharmaceuticals, agrochemicals, and advanced materials. The unique arrangement of bromine, fluorine, and iodine substituents on the benzene ring, coupled with the nitrile functional group, makes it a valuable intermediate in constructing complex molecular architectures.

The significance of 3-Bromo-2-fluoro-5-iodobenzonitrile lies in its role as a building block for synthesizing biologically active molecules. The presence of multiple halogen atoms enhances its reactivity, allowing for further functionalization through cross-coupling reactions, nucleophilic substitutions, and other transformations. These properties have made it a preferred choice for researchers aiming to develop novel therapeutic agents targeting various diseases.

In recent years, there has been a surge in research focused on halogenated benzonitriles due to their potential in drug discovery. A notable area of interest is their application in the synthesis of kinase inhibitors, which are critical in treating cancers and inflammatory diseases. For instance, studies have demonstrated that compounds derived from 3-Bromo-2-fluoro-5-iodobenzonitrile can serve as scaffolds for designing potent inhibitors of tyrosine kinases. These inhibitors have shown promise in preclinical trials by selectively blocking aberrant signaling pathways involved in tumor growth and progression.

Another emerging application of 3-Bromo-2-fluoro-5-iodobenzonitrile is in the development of antiviral drugs. The structural features of this compound allow it to interact with viral enzymes, disrupting their function and thereby inhibiting viral replication. Researchers have explored its derivatives as potential candidates against RNA viruses, including those responsible for influenza and hepatitis C. Preliminary findings suggest that certain modifications to the nitrile group can enhance binding affinity and reduce toxicity, making these compounds viable for further clinical development.

The synthesis of 3-Bromo-2-fluoro-5-iodobenzonitrile involves multi-step organic reactions that require precise control over reaction conditions to achieve high yields and purity. Typically, the process begins with the bromination and fluorination of a benzene precursor, followed by iodination at the desired position. The introduction of the nitrile group is often performed via cyanation reactions, which can be facilitated by metal catalysts such as palladium or copper complexes. Advances in catalytic methods have improved the efficiency and sustainability of these synthetic routes, reducing waste and energy consumption.

One of the key challenges in working with 3-Bromo-2-fluoro-5-iodobenzonitrile is its sensitivity to environmental conditions. Halogenated benzonitriles can undergo decomposition under prolonged exposure to light or heat, leading to side reactions and reduced yields. To mitigate these issues, researchers employ inert atmospheres and low temperatures during storage and manipulation. Additionally, purification techniques such as column chromatography or recrystallization are essential to isolate the desired product from impurities.

The growing demand for 3-Bromo-2-fluoro-5-iodobenzonitrile has prompted several chemical manufacturers to optimize production processes for scalability and cost-effectiveness. Continuous flow chemistry has emerged as a promising approach for synthesizing this compound efficiently on an industrial scale. This method allows for better control over reaction parameters, leading to consistent product quality and reduced solvent usage. Furthermore, green chemistry principles are being integrated into synthetic protocols to minimize environmental impact.

In conclusion,3-Bromo-2-fluoro-5-iodobenzonitrile (CAS No. 1160574-12-8) represents a critical intermediate in modern drug discovery and material science. Its unique structural features enable diverse chemical modifications, making it indispensable for designing novel therapeutics targeting various diseases. As research continues to uncover new applications for halogenated benzonitriles,3-Bromo-2-fluoro-5-iodobenzonitrile is poised to play an increasingly significant role in advancing scientific innovation.

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