Cas no 627527-17-7 (7-Bromo-2-naphthaldehyde)

7-Bromo-2-naphthaldehyde is a versatile aromatic aldehyde featuring a bromine substituent at the 7-position of the naphthalene ring. This compound serves as a valuable intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and functional materials. Its reactive aldehyde group enables facile derivatization, while the bromine moiety offers opportunities for further functionalization via cross-coupling reactions. The compound's rigid naphthalene backbone contributes to its stability and utility in constructing complex molecular architectures. It is commonly employed in Suzuki, Heck, and other palladium-catalyzed reactions, making it a useful building block for researchers in medicinal and materials chemistry.
7-Bromo-2-naphthaldehyde structure
7-Bromo-2-naphthaldehyde structure
Product Name:7-Bromo-2-naphthaldehyde
CAS No:627527-17-7
MF:C11H7BrO
MW:235.076682329178
MDL:MFCD09029699
CID:1642292
PubChem ID:11424850
Update Time:2025-06-07

7-Bromo-2-naphthaldehyde Chemical and Physical Properties

Names and Identifiers

    • 7-bromonaphthalene-2-carbaldehyde
    • 7-bromo-2-naphthalenecarbaldehyde
    • 7-bromo-naphthalene-2-carbaldehyde
    • CTK7H9806
    • 7-bromo-2-naphthalene-carbaldehyde
    • 7-bromo-2-naphthaldehyde
    • 2-Naphthalenecarboxaldehyde, 7-bromo-
    • AGN-PC-008UG1
    • QC-8090
    • AG-C-24430
    • 627527-17-7
    • DB-399955
    • 7-Bromo-2-naphthalenecarboxaldehyde
    • G67481
    • Z1269233153
    • EN300-3088362
    • SCHEMBL5783154
    • DTXSID60465474
    • CAB52717
    • AKOS015962700
    • 7-Bromo-2-naphthaldehyde
    • MDL: MFCD09029699
    • Inchi: 1S/C11H7BrO/c12-11-4-3-9-2-1-8(7-13)5-10(9)6-11/h1-7H
    • InChI Key: JJRAGKQULVEFTB-UHFFFAOYSA-N
    • SMILES: BrC1C=CC2=CC=C(C=O)C=C2C=1

Computed Properties

  • Exact Mass: 233.96801
  • Monoisotopic Mass: 233.96803g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 193
  • 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: 3.3
  • Topological Polar Surface Area: 17.1?2

Experimental Properties

  • PSA: 17.07

7-Bromo-2-naphthaldehyde Pricemore >>

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Additional information on 7-Bromo-2-naphthaldehyde

Introduction to 7-Bromo-2-naphthaldehyde (CAS No. 627527-17-7)

7-Bromo-2-naphthaldehyde, with the chemical formula C8H4Br2O, is a significant intermediate in the field of organic synthesis and pharmaceutical chemistry. This compound, identified by its CAS number 627527-17-7, has garnered attention due to its versatile applications in the development of fine chemicals and biologically active molecules. The presence of both a bromine substituent and an aldehyde group on the naphthalene core makes it a valuable building block for constructing more complex structures, particularly in medicinal chemistry.

The aldehyde functional group in 7-Bromo-2-naphthaldehyde serves as a reactive site for various chemical transformations, including condensation reactions, oxidation, and reduction processes. These reactions are pivotal in synthesizing heterocyclic compounds, which are widely prevalent in pharmaceuticals. The bromine atom, positioned at the 7-position of the naphthalene ring, introduces electrophilic characteristics that enhance its reactivity in cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig couplings. These reactions are instrumental in forming carbon-carbon bonds, a fundamental requirement for constructing complex molecular architectures.

In recent years, 7-Bromo-2-naphthaldehyde has been extensively explored in the synthesis of biologically active compounds. Its structural motif is frequently incorporated into drug candidates targeting various therapeutic areas, including oncology, neurology, and infectious diseases. For instance, studies have demonstrated its utility in generating Schiff bases and other imine derivatives, which exhibit potent pharmacological activities. The bromine substituent facilitates further functionalization via palladium-catalyzed reactions, enabling the introduction of diverse groups such as amines and thiols, thereby expanding the scope of possible derivatives.

One notable application of 7-Bromo-2-naphthaldehyde is in the development of small-molecule inhibitors for kinases and other enzymes involved in cancer progression. Researchers have leveraged its aldehyde group to form covalent bonds with key residues in target proteins, leading to the discovery of novel therapeutic agents. Additionally, its incorporation into peptidomimetics has shown promise in modulating protein-protein interactions relevant to inflammatory diseases. The compound’s ability to serve as a precursor for enantiomerically pure compounds has also been exploited in asymmetric synthesis, underscoring its importance in chiral drug development.

The synthetic methodologies involving 7-Bromo-2-naphthaldehyde have seen significant advancements due to its reactivity profile. Recent innovations include catalytic asymmetric hydrogenation to produce enantiomerically enriched aldehydes and brominated naphthalenes under mild conditions. These developments have not only improved yields but also reduced environmental impact by minimizing waste generation. Furthermore, flow chemistry approaches have been adapted for large-scale production of this compound, enhancing scalability for industrial applications.

From a computational chemistry perspective, the interaction between 7-Bromo-2-naphthaldehyde and biological targets has been scrutinized using molecular modeling techniques. These studies have provided insights into binding affinities and mechanism-of-action, guiding rational drug design efforts. The compound’s electronic properties have been particularly studied through density functional theory (DFT) calculations, revealing how electron distribution influences reactivity and binding interactions. Such computational insights are increasingly integrated into experimental workflows to accelerate the discovery process.

The role of 7-Bromo-2-naphthaldehyde in material science is also emerging as a promising area of research. Its ability to participate in polymerization reactions has led to the development of novel functional materials with applications ranging from coatings to electronic devices. The bromine moiety allows for controlled cross-linking and network formation, resulting in materials with tailored mechanical and thermal properties. This versatility positions 7-Bromo-2-naphthaldehyde as a multifaceted compound with broad industrial relevance.

In conclusion,7-Bromo-2-naphthaldehyde (CAS No. 627527-17-7) is a cornerstone intermediate with far-reaching implications across multiple scientific disciplines. Its unique structural features enable diverse synthetic transformations that are critical for pharmaceutical development, material science innovations, and fundamental research advancements. As our understanding of its reactivity evolves through interdisciplinary collaboration,7-Bromo-2-naphthaldehyde will undoubtedly continue to play a pivotal role in shaping future scientific discoveries.

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