Cas no 868860-65-5 (1-Allyl-3-bromo-5-fluorobenzene)

1-Allyl-3-bromo-5-fluorobenzene is a halogenated aromatic compound featuring an allyl substituent, bromine, and fluorine functional groups. Its distinct structure makes it a valuable intermediate in organic synthesis, particularly in cross-coupling reactions such as Suzuki-Miyaura or Heck couplings. The presence of both bromine and fluorine enhances its reactivity, allowing selective modifications at different positions. The allyl group further enables additional functionalization via olefin metathesis or radical reactions. This compound is well-suited for pharmaceutical and agrochemical research, where precise structural tuning is critical. Its stability under standard conditions ensures ease of handling and storage, making it a practical choice for synthetic applications.
1-Allyl-3-bromo-5-fluorobenzene structure
868860-65-5 structure
Product Name:1-Allyl-3-bromo-5-fluorobenzene
CAS No:868860-65-5
MF:C9H8BrF
MW:215.062225341797
CID:3165208
PubChem ID:69446193
Update Time:2025-10-18

1-Allyl-3-bromo-5-fluorobenzene Chemical and Physical Properties

Names and Identifiers

    • 1-Allyl-3-bromo-5-fluorobenzene
    • SCHEMBL5449546
    • DS-9852
    • 1-bromo-3-fluoro-5-prop-2-enylbenzene
    • AKOS026674287
    • CS-0456690
    • 868860-65-5
    • C76836
    • 816-986-8
    • MDL: A195435
    • Inchi: 1S/C9H8BrF/c1-2-3-7-4-8(10)6-9(11)5-7/h2,4-6H,1,3H2
    • InChI Key: RICOTNMALOCCKV-UHFFFAOYSA-N
    • SMILES: BrC1=CC(=CC(=C1)CC=C)F

Computed Properties

  • Exact Mass: 213.979
  • Monoisotopic Mass: 213.979
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 2
  • Complexity: 136
  • 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: 0A^2
  • XLogP3: 3.8

Experimental Properties

  • Color/Form: No data available
  • Density: 1.4±0.1 g/cm3
  • Melting Point: No data available
  • Boiling Point: 218.5±25.0 °C at 760 mmHg
  • Flash Point: 88.8±18.0 °C

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Additional information on 1-Allyl-3-bromo-5-fluorobenzene

Professional Introduction to 1-Allyl-3-bromo-5-fluorobenzene (CAS No. 868860-65-5)

1-Allyl-3-bromo-5-fluorobenzene, with the chemical formula C?H?BrF, is a significant compound in the field of organic synthesis and pharmaceutical research. This compound is characterized by its unique structural features, which include a benzene ring substituted with an allyl group, a bromine atom, and a fluorine atom. These substituents contribute to its versatile reactivity and make it a valuable intermediate in the synthesis of various bioactive molecules.

The allyl group in 1-Allyl-3-bromo-5-fluorobenzene introduces a double bond that can participate in various chemical reactions, such as cross-coupling reactions, which are widely used in the preparation of complex organic molecules. The bromo substituent provides a handle for further functionalization via nucleophilic substitution reactions, allowing for the introduction of diverse functional groups. The fluorine atom, on the other hand, enhances the metabolic stability of the molecule and can influence its electronic properties, making it an attractive component in drug design.

In recent years, 1-Allyl-3-bromo-5-fluorobenzene has garnered attention in the pharmaceutical industry due to its potential applications in the development of novel therapeutic agents. Its structural motifs are found in several pharmacophores that exhibit desirable biological activities. For instance, benzene derivatives with fluorine and bromine substituents have been shown to possess anti-inflammatory, antiviral, and anticancer properties. The presence of an allyl group further expands its utility as a building block for more complex scaffolds.

One of the most promising applications of 1-Allyl-3-bromo-5-fluorobenzene is in the synthesis of kinase inhibitors. Kinases are enzymes that play a crucial role in cell signaling pathways and are often targeted in cancer therapy. Researchers have utilized this compound as a precursor to develop small-molecule inhibitors that can modulate kinase activity. The combination of the allyl and bromo groups allows for selective modifications that can fine-tune the binding affinity and selectivity of these inhibitors towards specific kinases.

Moreover, 1-Allyl-3-bromo-5-fluorobenzene has been explored in the development of Fluorescent Resonance Energy Transfer (FRET) probes for bioimaging applications. FRET probes are widely used in cellular imaging to study protein-protein interactions and other dynamic processes within cells. The fluorine atom in this compound can act as an electron-withdrawing group, enhancing the fluorescence properties of the molecule when coupled with appropriate dyes. This makes it a valuable tool for researchers studying intracellular events.

The compound's reactivity also makes it useful in materials science applications. For example, it can be used to synthesize polymers with tailored electronic properties by incorporating it into conjugated systems. These polymers have potential applications in organic electronics, such as organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs). The allyl group facilitates polymerization reactions, while the bromo and fluorine substituents can influence the optoelectronic properties of the resulting materials.

In academic research, 1-Allyl-3-bromo-5-fluorobenzene has been employed as a key intermediate in synthetic chemistry studies aimed at developing new synthetic methodologies. Its unique structure provides chemists with opportunities to explore novel reaction pathways and develop more efficient synthetic routes to complex molecules. These efforts contribute to the broader advancement of organic synthesis and provide valuable tools for future research.

The pharmaceutical industry continues to invest heavily in discovering new active ingredients derived from benzene derivatives like 1-Allyl-3-bromo-5-fluorobenzene. The demand for innovative drugs that address unmet medical needs has driven significant interest in this class of compounds. Researchers are leveraging its structural features to design molecules with improved efficacy and reduced side effects. Collaborative efforts between academia and industry are essential to translate these findings into tangible therapeutic benefits for patients.

As our understanding of biological systems grows, so does the need for sophisticated tools to study them at the molecular level. Compounds like 1-Allyl-3-bromo-5-fluorobenzene play a critical role in this endeavor by serving as versatile building blocks for probes and inhibitors. Their ability to modulate biological processes makes them indispensable tools for researchers seeking to unravel the complexities of life.

In conclusion, 1-Allyl-3-bromo-5-fluorobenzene (CAS No. 868860-65-5) is a multifaceted compound with significant potential across various fields of science and technology. Its unique structural features make it a valuable intermediate in pharmaceutical synthesis, bioimaging, materials science, and organic synthesis research. As scientific understanding progresses, we can expect this compound to continue playing a pivotal role in advancing our knowledge and capabilities.

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