Cas no 1806518-24-0 (2-Bromo-4-nitrophenylpropanal)

2-Bromo-4-nitrophenylpropanal is a brominated nitro-substituted phenylpropanal compound, primarily utilized as an intermediate in organic synthesis and pharmaceutical research. Its distinct structure, featuring both bromo and nitro functional groups, enables selective reactivity in cross-coupling reactions, nucleophilic substitutions, and other transformations. The compound's electron-withdrawing nitro group enhances its utility in electrophilic aromatic substitution processes, while the bromine atom offers versatility for further derivatization. Suitable for controlled synthetic applications, it is commonly employed in the development of fine chemicals and bioactive molecules. Proper handling is advised due to its potential reactivity, and storage under inert conditions is recommended to maintain stability.
2-Bromo-4-nitrophenylpropanal structure
2-Bromo-4-nitrophenylpropanal structure
Product Name:2-Bromo-4-nitrophenylpropanal
CAS No:1806518-24-0
MF:C9H8BrNO3
MW:258.06872177124
CID:4961728
PubChem ID:165478741
Update Time:2025-05-26

2-Bromo-4-nitrophenylpropanal Chemical and Physical Properties

Names and Identifiers

    • 2-Bromo-4-nitrophenylpropanal
    • Inchi: 1S/C9H8BrNO3/c1-6(5-12)8-3-2-7(11(13)14)4-9(8)10/h2-6H,1H3
    • InChI Key: VBUQSSHUZPWUDK-UHFFFAOYSA-N
    • SMILES: BrC1C=C(C=CC=1C(C=O)C)[N+](=O)[O-]

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 2
  • Complexity: 229
  • XLogP3: 2.4
  • Topological Polar Surface Area: 62.9

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2-Bromo-4-nitrophenylpropanal Related Literature

Additional information on 2-Bromo-4-nitrophenylpropanal

Professional Introduction to 2-Bromo-4-nitrophenylpropanal (CAS No. 1806518-24-0)

2-Bromo-4-nitrophenylpropanal, identified by the Chemical Abstracts Service Number (CAS No.) 1806518-24-0, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical chemistry and synthetic biology due to its unique structural and functional properties. This compound belongs to the class of aromatic aldehydes, characterized by a benzene ring substituted with bromine and nitro groups, coupled with an aldehyde functional group at the propyl side chain. The precise arrangement of these substituents imparts distinct reactivity and makes it a valuable intermediate in the synthesis of more complex molecules.

The bromo and nitro substituents on the phenyl ring play a crucial role in determining the compound's chemical behavior. The bromine atom, being highly electronegative, influences the electron density distribution across the aromatic system, making certain positions more susceptible to nucleophilic attack. On the other hand, the nitro group, a strong electron-withdrawing moiety, not only affects the aromaticity but also introduces polarity and reactivity that can be exploited in synthetic pathways. These features make 2-Bromo-4-nitrophenylpropanal a versatile building block for constructing heterocyclic compounds, which are prevalent in many biologically active molecules.

In recent years, there has been growing interest in leveraging such halogenated aromatic aldehydes for the development of novel therapeutic agents. The presence of both bromine and nitro groups on the same aromatic core provides multiple handles for further functionalization, enabling chemists to design molecules with tailored properties. For instance, palladium-catalyzed cross-coupling reactions are frequently employed to introduce additional aryl or vinyl groups, expanding the structural diversity of derivatives. These transformations have been instrumental in generating libraries of compounds for high-throughput screening, a common strategy in drug discovery pipelines.

One particularly notable application of 2-Bromo-4-nitrophenylpropanal is in the synthesis of kinase inhibitors. Kinases are enzymes that play pivotal roles in cellular signaling pathways, and their dysregulation is implicated in numerous diseases, including cancer. By designing small molecules that selectively inhibit specific kinases, researchers aim to develop targeted therapies with improved efficacy and reduced side effects. The aldehyde group in 2-Bromo-4-nitrophenylpropanal serves as a convenient site for conjugation with other pharmacophores that can interact with the kinase active site or allosteric pockets. Additionally, the electronic properties influenced by the bromo and nitro groups can be fine-tuned to optimize binding affinity and selectivity.

Another area where this compound has shown promise is in the development of probes for biochemical studies. Aldehydes are well-known for their ability to react with nucleophiles such as amines and thiols, forming stable adducts. This reactivity has been exploited to label proteins or other biomolecules with fluorescent or affinity tags for analytical purposes. The unique combination of substituents in 2-Bromo-4-nitrophenylpropanal allows for orthogonal labeling strategies, enabling researchers to study multiple targets simultaneously without interference.

The synthesis of 2-Bromo-4-nitrophenylpropanal typically involves multi-step organic transformations starting from commercially available precursors like 4-nitrotoluene or 4-bromonitrobenzaldehyde. Key steps often include bromination at the appropriate position on the aromatic ring followed by reduction or formylation to introduce the aldehyde functionality at the propyl side chain. Advances in catalytic methods have significantly improved the efficiency and scalability of these processes, making it feasible to produce this compound in quantities suitable for research applications.

In conclusion, 2-Bromo-4-nitrophenylpropanal (CAS No. 1806518-24-0) represents a fascinating compound with broad utility in pharmaceutical and biochemical research. Its unique structural features enable diverse synthetic possibilities, making it an indispensable tool for chemists striving to develop innovative therapeutics and diagnostic agents. As our understanding of molecular interactions continues to evolve, compounds like this will undoubtedly play an increasingly critical role in advancing scientific discovery.

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