Cas no 108940-96-1 (3,5-Dibromo-4-methoxybenzaldehyde)

3,5-Dibromo-4-methoxybenzaldehyde is a brominated aromatic aldehyde with a methoxy substituent, widely used as an intermediate in organic synthesis and pharmaceutical research. Its key advantages include high reactivity due to the aldehyde functional group, which facilitates further derivatization, and the presence of bromine atoms that enhance its utility in cross-coupling reactions, such as Suzuki or Heck couplings. The methoxy group contributes to electronic modulation, improving selectivity in certain transformations. This compound is particularly valuable in the synthesis of complex molecules, including agrochemicals and bioactive compounds, owing to its stability and well-defined reactivity profile under controlled conditions.
3,5-Dibromo-4-methoxybenzaldehyde structure
108940-96-1 structure
Product Name:3,5-Dibromo-4-methoxybenzaldehyde
CAS No:108940-96-1
MF:C8H6Br2O2
MW:293.940041065216
MDL:MFCD00858984
CID:1083389
PubChem ID:1494332
Update Time:2025-05-22

3,5-Dibromo-4-methoxybenzaldehyde Chemical and Physical Properties

Names and Identifiers

    • 3,5-Dibromo-4-methoxybenzaldehyde
    • 3,5-Dibrom-4-methoxy-benzaldehyd
    • 3,5-dibromo-4-methoxy-benzaldehyde
    • 3,5-dibromoanisaldehyde
    • 3,5-dibromo-p-anisaldehyde
    • AC1LSSY1
    • AC1Q44LU
    • BBL022969
    • CTK4A6248
    • STK039821
    • AB0036448
    • ST24041194
    • Y3645
    • 108940-96-1
    • AKOS000290641
    • A895167
    • Z57772454
    • MFCD00858984
    • CHEBI:206456
    • CS-0061915
    • DTXSID40973986
    • 5844-80-4
    • s10819
    • DB-365742
    • SY025710
    • SCHEMBL2588646
    • AS-19677
    • EN300-41709
    • DTXCID001401425
    • MDL: MFCD00858984
    • Inchi: 1S/C8H6Br2O2/c1-12-8-6(9)2-5(4-11)3-7(8)10/h2-4H,1H3
    • InChI Key: CAGHJINSPMGDKT-UHFFFAOYSA-N
    • SMILES: BrC1C=C(C=O)C=C(C=1OC)Br

Computed Properties

  • Exact Mass: 291.87338
  • Monoisotopic Mass: 291.87345g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • Complexity: 151
  • 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: 26.3
  • XLogP3: 2.7

Experimental Properties

  • Density: 1.866±0.06 g/cm3 (20 oC 760 Torr),
  • Melting Point: 90-91 oC
  • Boiling Point: 332.0±37.0℃/760mmHg
  • Solubility: Almost insoluble (0.053 g/l) (25 o C),
  • PSA: 26.3

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Additional information on 3,5-Dibromo-4-methoxybenzaldehyde

3,5-Dibromo-4-methoxybenzaldehyde (CAS No: 108940-96-1)

3,5-Dibromo-4-methoxybenzaldehyde is a versatile aromatic compound with significant applications in organic synthesis and materials science. This compound, identified by the CAS registry number 108940-96-1, has garnered attention in recent years due to its unique chemical properties and potential for use in advanced materials and pharmaceuticals. The molecule consists of a benzene ring substituted with two bromine atoms at the 3 and 5 positions, a methoxy group at the 4 position, and an aldehyde group at the para position relative to the methoxy group.

The structure of 3,5-dibromo-4-methoxybenzaldehyde makes it highly reactive in various chemical transformations. The presence of electron-withdrawing groups like bromine and the electron-donating methoxy group creates a unique electronic environment on the benzene ring, which can be exploited in cross-coupling reactions, electrophilic substitutions, and other organic transformations. Recent studies have highlighted its utility as a precursor for synthesizing biologically active molecules and functional materials.

One of the most promising applications of 3,5-dibromo-4-methoxybenzaldehyde lies in its use as a building block for constructing complex aromatic systems. Researchers have demonstrated that this compound can undergo Suzuki-Miyaura coupling reactions to form biaryl structures with high efficiency. These biaryl compounds are valuable in drug discovery and materials science due to their enhanced electronic properties and structural diversity.

In addition to its role in organic synthesis, 3,5-dibromo-4-methoxybenzaldehyde has been explored for its potential in catalysis. The bromine substituents on the benzene ring can act as directing groups, facilitating the formation of metal complexes that exhibit catalytic activity in various reactions. Recent advancements in heterogeneous catalysis have leveraged this property to develop more sustainable and efficient catalysts for industrial applications.

The synthesis of 3,5-dibromo-4-methoxybenzaldehyde typically involves multi-step processes that combine bromination, alkylation, and oxidation reactions. One common approach involves the bromination of 4-methoxybenzaldehyde using bromine in a suitable solvent under controlled conditions. This method ensures high yields and excellent regioselectivity due to the directing effects of the methoxy group.

From an environmental standpoint, 3,5-dibromo-4-methoxybenzaldehyde has been studied for its biodegradation potential and toxicity profile. Recent research indicates that this compound exhibits moderate biodegradability under aerobic conditions, making it less persistent in aquatic environments compared to other halogenated aromatic compounds. However, further studies are required to fully understand its environmental impact and develop strategies for safe disposal.

In conclusion, 3,5-dibromo-4-methoxybenzaldehyde (CAS No: 108940-96-1) is a multifaceted compound with significant potential in organic synthesis, catalysis, and materials science. Its unique chemical properties and reactivity make it an invaluable tool for researchers seeking to develop novel compounds with tailored functionalities. As ongoing research continues to uncover new applications for this compound, it is poised to play an increasingly important role in both academic and industrial settings.

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