Cas no 359867-42-8 (3-Amino-4-bromobenzaldehyde (Technical Grade))

3-Amino-4-bromobenzaldehyde (Technical Grade) is a brominated aromatic aldehyde with an amino substituent, commonly utilized as an intermediate in organic synthesis and pharmaceutical manufacturing. Its reactive aldehyde and amino groups enable versatile applications in the preparation of heterocyclic compounds, dyes, and agrochemicals. The bromine moiety further enhances its utility in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings. Technical grade material is suitable for industrial processes where high purity is not critical, offering a cost-effective solution for bulk synthesis. The compound exhibits moderate stability under standard conditions but should be stored in a cool, dry environment to minimize degradation.
3-Amino-4-bromobenzaldehyde (Technical Grade) structure
359867-42-8 structure
Product Name:3-Amino-4-bromobenzaldehyde (Technical Grade)
CAS No:359867-42-8
MF:C7H6BrNO
MW:200.03264093399
MDL:MFCD11858306
CID:1004822
PubChem ID:23497537
Update Time:2025-06-08

3-Amino-4-bromobenzaldehyde (Technical Grade) Chemical and Physical Properties

Names and Identifiers

    • 3-Amino-4-bromo-benzaldehyde
    • 3-amino-4-bromobenzaldehyde
    • AT23717
    • SCHEMBL2278898
    • SB36817
    • DB-069292
    • NEMFHQCQKJUENY-UHFFFAOYSA-N
    • Benzaldehyde, 3-amino-4-bromo-
    • 359867-42-8
    • MFCD11858306
    • DTXSID70634497
    • BS-28303
    • CS-0029751
    • 3-Amino-4-bromobenzaldehyde, tech grade
    • 3-Amino-4-bromobenzaldehyde (Technical Grade)
    • MDL: MFCD11858306
    • Inchi: 1S/C7H6BrNO/c8-6-2-1-5(4-10)3-7(6)9/h1-4H,9H2
    • InChI Key: NEMFHQCQKJUENY-UHFFFAOYSA-N
    • SMILES: BrC1=CC=C(C=O)C=C1N

Computed Properties

  • Exact Mass: 198.96300
  • Monoisotopic Mass: 198.96328g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 1
  • Complexity: 129
  • 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: 1.4
  • Topological Polar Surface Area: 43.1?2

Experimental Properties

  • PSA: 43.09000
  • LogP: 2.42500

3-Amino-4-bromobenzaldehyde (Technical Grade) Pricemore >>

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Additional information on 3-Amino-4-bromobenzaldehyde (Technical Grade)

Introduction to 3-Amino-4-bromobenzaldehyde (Technical Grade) and Its Significance in Modern Chemical Research

3-Amino-4-bromobenzaldehyde (Technical Grade), with the CAS number 359867-42-8, is a versatile intermediate compound that has garnered significant attention in the field of organic synthesis and pharmaceutical research. This compound, characterized by its amino and bromo substituents on a benzaldehyde backbone, serves as a crucial building block for the development of various bioactive molecules. Its unique structural features make it particularly valuable in the synthesis of heterocyclic compounds, which are widely explored for their potential therapeutic applications.

The 3-amino-4-bromobenzaldehyde molecule exhibits a high degree of reactivity due to the presence of both an amino group and a bromine atom. These functional groups allow for diverse chemical transformations, including nucleophilic aromatic substitution, cross-coupling reactions, and condensation reactions. Such reactivity is exploited in synthetic protocols to construct complex molecular architectures, making this compound indispensable in medicinal chemistry laboratories.

In recent years, there has been a surge in research focused on developing novel therapeutic agents targeting neurological disorders. 3-Amino-4-bromobenzaldehyde has emerged as a key intermediate in the synthesis of small-molecule inhibitors that modulate neurotransmitter receptors. For instance, studies have demonstrated its utility in constructing benzodiazepine analogs, which exhibit potential anxiolytic and sedative properties. The bromine substituent facilitates further functionalization via palladium-catalyzed cross-coupling reactions, enabling the introduction of additional pharmacophores that enhance binding affinity and selectivity.

Another area where 3-amino-4-bromobenzaldehyde has shown promise is in the development of anticancer agents. Researchers have leveraged its reactivity to synthesize benzimidazole derivatives known for their inhibitory effects on kinases and other enzymes involved in tumor proliferation. The amino group allows for facile coupling with carboxylic acid-containing molecules, while the bromine atom serves as a handle for subsequent Suzuki-Miyaura couplings. These transformations have led to the discovery of several lead compounds with significant antitumor activity.

The pharmaceutical industry also values 3-amino-4-bromobenzaldehyde for its role in producing antimicrobial agents. The structural motif is found in numerous natural products with known antibacterial and antifungal properties. By modifying the substituents on the benzaldehyde ring, chemists can fine-tune the activity spectrum of these compounds against resistant strains of pathogens. The technical-grade quality ensures consistency in purity and reactivity, which is critical for large-scale synthesis and subsequent clinical trials.

Advances in computational chemistry have further enhanced the utility of 3-amino-4-bromobenzaldehyde by enabling rapid virtual screening of potential drug candidates. Molecular modeling studies suggest that derivatives of this compound can interact with specific biological targets through hydrogen bonding networks formed by the amino group. Additionally, the bromine atom can participate in halogen bonding interactions, which are increasingly recognized as important non-covalent forces in drug design.

The synthesis of 3-amino-4-bromobenzaldehyde itself is an intriguing process that highlights modern synthetic methodologies. Traditional approaches often involve multi-step sequences starting from readily available aromatic precursors. However, recent innovations have enabled more efficient routes, including one-pot reactions that minimize waste and improve yields. These advancements align with global efforts to promote sustainable chemistry practices.

Industrial applications of 3-amino-4-bromobenzaldehyde extend beyond pharmaceuticals into materials science. For example, it serves as a precursor for synthesizing conductive polymers used in organic electronics. The ability to introduce various functional groups onto its structure allows chemists to tailor electrical properties such as conductivity and stability for specific applications.

Regulatory considerations play a significant role in the handling and distribution of 3-amino-4-bromobenzaldehyde. While it is not classified as a hazardous material under current guidelines, proper storage conditions must be maintained to prevent degradation or unwanted side reactions. Manufacturers provide detailed safety data sheets (SDS) to ensure that users are aware of necessary precautions when working with this compound.

The future prospects for 3-amino-4-bromobenzaldehyde are bright, driven by ongoing research into novel bioactive molecules and innovative synthetic techniques. As our understanding of disease mechanisms deepens, so does the demand for sophisticated molecular tools like this intermediate compound. Collaborative efforts between academia and industry will continue to accelerate discoveries that could lead to breakthrough treatments for unmet medical needs.

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