Cas no 477535-40-3 (3,5-Dibromo-2-fluorobenzaldehyde)

3,5-Dibromo-2-fluorobenzaldehyde is a halogenated aromatic aldehyde with the molecular formula C7H3Br2FO. This compound features bromine and fluorine substituents at the 3,5- and 2-positions, respectively, enhancing its reactivity and utility in selective organic transformations. Its electron-withdrawing groups make it a valuable intermediate in Suzuki-Miyaura cross-coupling reactions, nucleophilic aromatic substitutions, and other palladium-catalyzed processes. The presence of both bromine and fluorine atoms allows for further functionalization, enabling precise modifications in pharmaceutical and agrochemical synthesis. With high purity and stability under standard conditions, it is suitable for research and industrial applications requiring regioselective control. Proper handling is advised due to its potential sensitivity to moisture and light.
3,5-Dibromo-2-fluorobenzaldehyde structure
477535-40-3 structure
Product Name:3,5-Dibromo-2-fluorobenzaldehyde
CAS No:477535-40-3
MF:C7H3Br2FO
MW:281.904524087906
MDL:MFCD03094096
CID:1029221
PubChem ID:2773968
Update Time:2025-06-12

3,5-Dibromo-2-fluorobenzaldehyde Chemical and Physical Properties

Names and Identifiers

    • 3,5-Dibromo-2-fluorobenzaldehyde
    • AC1MCNQG
    • AG-A-48273
    • CTK7H8566
    • MolPort-001-771-289
    • PC0751
    • PubChem8457
    • AK136538
    • 4.77535403E8
    • 9538AF
    • LS10208
    • CM11918
    • AS05574
    • FCH1320982
    • BC003348
    • AX8258106
    • 3,5-Dibromo-2-fluorobenzaldehyde, AldrichCPR
    • DTXSID90378806
    • MFCD03094096
    • SCHEMBL1592418
    • DB-365738
    • 477535-40-3
    • AKOS022171944
    • A856623
    • 3,5-dibromo-2-fluoro-benzaldehyde
    • CS-0059170
    • CUA53540
    • DS-5537
    • MDL: MFCD03094096
    • Inchi: 1S/C7H3Br2FO/c8-5-1-4(3-11)7(10)6(9)2-5/h1-3H
    • InChI Key: UZLJTDXCWOCFJP-UHFFFAOYSA-N
    • SMILES: BrC1=CC(=CC(C=O)=C1F)Br

Computed Properties

  • Exact Mass: 281.85142g/mol
  • Monoisotopic Mass: 279.85347g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 153
  • 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: 17.1
  • XLogP3: 2.9

Experimental Properties

  • Density: 2.047±0.06 g/cm3 (20 oC 760 Torr),
  • Boiling Point: 280.1±35.0 oC (760 Torr),
  • Flash Point: 123.2±25.9 oC,
  • Solubility: Almost insoluble (0.048 g/l) (25 o C),

3,5-Dibromo-2-fluorobenzaldehyde Security Information

  • Hazard Statement: Irritant
  • Hazardous Material Identification: Xi

3,5-Dibromo-2-fluorobenzaldehyde Pricemore >>

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Additional information on 3,5-Dibromo-2-fluorobenzaldehyde

Recent Advances in the Application of 3,5-Dibromo-2-fluorobenzaldehyde (CAS: 477535-40-3) in Chemical Biology and Pharmaceutical Research

3,5-Dibromo-2-fluorobenzaldehyde (CAS: 477535-40-3) has emerged as a versatile building block in medicinal chemistry and chemical biology research. Recent studies have highlighted its importance as a key intermediate in the synthesis of various biologically active compounds. This halogen-rich aromatic aldehyde offers unique reactivity patterns due to the strategic placement of bromine and fluorine substituents, making it particularly valuable for structure-activity relationship (SAR) studies and drug discovery programs.

In a 2023 study published in the Journal of Medicinal Chemistry, researchers utilized 3,5-Dibromo-2-fluorobenzaldehyde as a starting material for the development of novel kinase inhibitors. The compound's ability to undergo selective cross-coupling reactions while maintaining the aldehyde functionality proved crucial for creating diverse molecular architectures. The research team reported significant improvements in inhibitor potency and selectivity when compared to previous generations of compounds, demonstrating the value of this building block in rational drug design.

Recent synthetic methodology developments have expanded the utility of 477535-40-3 in pharmaceutical applications. A 2024 publication in Organic Letters described an efficient palladium-catalyzed amination protocol that preserves the aldehyde group while allowing for selective modification of the bromine positions. This advancement has enabled more streamlined routes to complex drug candidates, particularly in the area of CNS-targeted therapeutics where the fluorinated aromatic core shows favorable blood-brain barrier penetration properties.

The compound has also found applications in chemical biology probe development. A Nature Chemical Biology paper from early 2024 reported the use of 3,5-Dibromo-2-fluorobenzaldehyde derivatives as covalent inhibitors for studying protein-protein interactions. The researchers designed activity-based probes that could selectively label target proteins in live cells, providing new tools for understanding disease mechanisms at the molecular level.

From a safety and handling perspective, recent material safety data sheet (MSDS) updates for 477535-40-3 have provided more detailed information about its storage conditions and reactivity. These updates reflect the growing body of knowledge about handling halogenated aromatic aldehydes in research settings, emphasizing the need for proper ventilation and personal protective equipment when working with this compound.

Looking forward, the unique properties of 3,5-Dibromo-2-fluorobenzaldehyde continue to attract attention in pharmaceutical development. Current research directions include its incorporation into PROTAC (proteolysis targeting chimera) molecules and its use in fragment-based drug discovery platforms. The compound's combination of halogen atoms for potential halogen bonding interactions and the reactive aldehyde group for further derivatization makes it particularly valuable for these emerging therapeutic approaches.

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