Cas no 1628507-86-7 (1-(4-Borono-2-fluorophenyl)cyclopropane-1-carboxylic acid)

1-(4-Borono-2-fluorophenyl)cyclopropane-1-carboxylic acid is a boronic acid derivative featuring a cyclopropane carboxylic acid scaffold and a fluorine-substituted aromatic ring. This compound is of interest in medicinal chemistry and organic synthesis due to its unique structural properties, which facilitate its use as a versatile building block in Suzuki-Miyaura cross-coupling reactions. The presence of both boronic acid and carboxylic acid functional groups enhances its utility in bioconjugation and the development of bioactive molecules. The fluorine substitution may improve metabolic stability and binding affinity in drug design applications. Its well-defined reactivity profile makes it suitable for precise synthetic modifications in pharmaceutical research and material science.
1-(4-Borono-2-fluorophenyl)cyclopropane-1-carboxylic acid structure
1628507-86-7 structure
Product Name:1-(4-Borono-2-fluorophenyl)cyclopropane-1-carboxylic acid
CAS No:1628507-86-7
MF:C10H10BFO4
MW:223.993406772614
MDL:MFCD21609532
CID:4609774
Update Time:2025-05-20

1-(4-Borono-2-fluorophenyl)cyclopropane-1-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 1-(4-borono-2-fluorophenyl)cyclopropane-1-carboxylic acid
    • W2839
    • 1-(4-Borono-2-fluorophenyl)cyclopropane-1-carboxylic acid
    • MDL: MFCD21609532
    • Inchi: 1S/C10H10BFO4/c12-8-5-6(11(15)16)1-2-7(8)10(3-4-10)9(13)14/h1-2,5,15-16H,3-4H2,(H,13,14)
    • InChI Key: ZLVIHPPSVIXBSY-UHFFFAOYSA-N
    • SMILES: FC1C=C(B(O)O)C=CC=1C1(C(=O)O)CC1

Computed Properties

  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 3
  • Complexity: 293
  • Topological Polar Surface Area: 77.8

Experimental Properties

  • Density: 1.5±0.1 g/cm3
  • Boiling Point: 445.8±55.0 °C at 760 mmHg
  • Flash Point: 223.4±31.5 °C
  • Vapor Pressure: 0.0±1.1 mmHg at 25°C

1-(4-Borono-2-fluorophenyl)cyclopropane-1-carboxylic acid Security Information

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Additional information on 1-(4-Borono-2-fluorophenyl)cyclopropane-1-carboxylic acid

Introduction to 1-(4-Borono-2-fluorophenyl)cyclopropane-1-carboxylic acid (CAS No. 1628507-86-7)

1-(4-Borono-2-fluorophenyl)cyclopropane-1-carboxylic acid (CAS No. 1628507-86-7) is a sophisticated organic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound, characterized by its unique structural features, including a cyclopropane ring and a boronic acid moiety attached to a fluorophenyl group, exhibits promising potential in the development of novel therapeutic agents. The presence of these functional groups not only enhances its chemical reactivity but also opens up diverse possibilities for its application in drug design and synthesis.

The boronic acid component of this molecule is particularly noteworthy, as boronic acids are well-known for their role in various biological processes and have been extensively studied for their applications in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern organic synthesis. This reaction is pivotal in constructing complex molecular architectures, which are often required in the development of biologically active compounds. The fluorophenyl group, on the other hand, introduces a fluorine atom into the aromatic ring, a modification that is frequently employed to improve metabolic stability, binding affinity, and overall pharmacological properties of drug candidates.

The cyclopropane ring is another key structural feature that contributes to the unique chemical profile of this compound. Cyclopropanes are known for their strained three-membered ring structure, which can lead to high reactivity and interesting electronic properties. This strain can be exploited to facilitate various chemical transformations, making cyclopropane-containing compounds valuable intermediates in synthetic chemistry. Moreover, the incorporation of cyclopropane units into drug molecules has been shown to enhance their bioavailability and binding interactions with biological targets.

In recent years, there has been a surge in research focused on developing new methodologies for the synthesis of fluorinated aromatic compounds due to their widespread use in pharmaceuticals. The compound 1-(4-Borono-2-fluorophenyl)cyclopropane-1-carboxylic acid exemplifies this trend, as it combines the advantages of both fluorine-containing systems and boronic acids. The fluorine atom can modulate electronic effects and influence the conformational preferences of the molecule, while the boronic acid moiety provides a versatile handle for further functionalization.

One of the most exciting applications of this compound lies in its potential use as a building block for the synthesis of more complex molecules with therapeutic implications. For instance, researchers have explored its utility in generating novel heterocyclic scaffolds by incorporating it into multi-step synthetic routes. These heterocycles are often found in bioactive natural products and have been successfully translated into pharmacologically relevant entities. The combination of cyclopropane, boronic acid, and fluorophenyl moieties offers a rich palette of possibilities for medicinal chemists to explore.

The interest in 1-(4-Borono-2-fluorophenyl)cyclopropane-1-carboxylic acid has also been fueled by its potential role in addressing emerging challenges in drug discovery. With an increasing demand for innovative therapeutic solutions, particularly in areas such as oncology and infectious diseases, the development of new molecular entities is crucial. This compound represents a promising candidate due to its unique structural attributes and the potential synergistic effects arising from its multiple functional groups.

Recent advancements in computational chemistry have further enhanced our ability to predict and optimize the properties of such compounds. By leveraging computational tools, researchers can now design experiments more efficiently and tailor molecular structures to meet specific pharmacological requirements. The virtual screening and molecular modeling studies have identified 1-(4-Borono-2-fluorophenyl)cyclopropane-1-carboxylic acid as a valuable starting point for developing novel drug candidates.

The synthesis of this compound involves sophisticated organic transformations that highlight the ingenuity of modern synthetic strategies. Key steps include the introduction of the boronic acid functionality via lithiation-borylation sequences followed by ring-closing metathesis to form the cyclopropane unit. These reactions require precise control over reaction conditions to ensure high yields and purity. The integration of fluorine into the aromatic ring is typically achieved through metal-catalyzed cross-coupling reactions or direct fluorination methods.

The pharmacological potential of 1-(4-Borono-2-fluorophenyl)cyclopropane-1-carboxylic acid has been investigated through various experimental approaches. Initial studies have suggested that it may exhibit inhibitory activity against certain enzymes and receptors relevant to human health conditions. These findings are particularly encouraging given the growing body of evidence supporting the importance of fluorinated compounds in medicinal chemistry.

The versatility of this compound extends beyond its role as an intermediate in drug synthesis; it also serves as a model system for studying electronic effects and steric influences on molecular reactivity. By comparing its behavior with structurally related compounds, researchers can gain deeper insights into how different substituents influence chemical properties at both atomic and molecular levels.

In conclusion,1-(4-Borono-2-fluorophenyl)cyclopropane-1-carboxylic acid (CAS No. 1628507-86-7) stands out as a multifaceted compound with significant implications for pharmaceutical research and development. Its unique structural composition opens up numerous avenues for innovation, making it an attractive scaffold for designing next-generation therapeutics aimed at addressing unmet medical needs across various therapeutic domains.

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