Cas no 1456863-37-8 (2-Bromopyrimidine-5-carbaldehyde)

2-Bromopyrimidine-5-carbaldehyde is a versatile heterocyclic building block widely used in pharmaceutical and agrochemical synthesis. Its key functional groups—a bromine substituent and an aldehyde moiety—enable diverse reactivity, facilitating cross-coupling reactions, nucleophilic substitutions, and condensations. The electron-deficient pyrimidine core enhances its utility in constructing complex molecular architectures. This compound is particularly valuable in medicinal chemistry for the development of kinase inhibitors and other bioactive molecules. High purity and stability under standard conditions ensure consistent performance in synthetic applications. Its well-defined reactivity profile makes it a preferred intermediate for targeted modifications in drug discovery and material science.
2-Bromopyrimidine-5-carbaldehyde structure
1456863-37-8 structure
Product Name:2-Bromopyrimidine-5-carbaldehyde
CAS No:1456863-37-8
MF:C5H3BrN2O
MW:186.994119882584
MDL:MFCD25371819
CID:4600746
PubChem ID:75480598
Update Time:2025-06-11

2-Bromopyrimidine-5-carbaldehyde Chemical and Physical Properties

Names and Identifiers

    • 2-Bromopyrimidine-5-carbaldehyde
    • 2-Bromo-pyrimidine-5-carbaldehyde
    • 5-Pyrimidinecarboxaldehyde, 2-bromo-
    • SB56555
    • MDL: MFCD25371819
    • Inchi: 1S/C5H3BrN2O/c6-5-7-1-4(3-9)2-8-5/h1-3H
    • InChI Key: SYXSPPBOICULFV-UHFFFAOYSA-N
    • SMILES: BrC1=NC=C(C=O)C=N1

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 1
  • Complexity: 101
  • XLogP3: 0.7
  • Topological Polar Surface Area: 42.8

2-Bromopyrimidine-5-carbaldehyde Pricemore >>

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Additional information on 2-Bromopyrimidine-5-carbaldehyde

Introduction to 2-Bromopyrimidine-5-carbaldehyde (CAS No. 1456863-37-8)

2-Bromopyrimidine-5-carbaldehyde, identified by the Chemical Abstracts Service Number (CAS No.) 1456863-37-8, is a significant intermediate in the field of organic synthesis and pharmaceutical chemistry. This compound belongs to the pyrimidine derivatives, a class of heterocyclic aromatic compounds that play a crucial role in the development of various bioactive molecules. The structural features of 2-Bromopyrimidine-5-carbaldehyde, including the presence of a bromine substituent at the 2-position and an aldehyde group at the 5-position, make it a versatile building block for constructing more complex molecular architectures.

The synthesis and application of 2-Bromopyrimidine-5-carbaldehyde have garnered considerable attention in recent years due to its utility in medicinal chemistry and materials science. The bromine atom at the 2-position provides a reactive handle for further functionalization via cross-coupling reactions, such as Suzuki-Miyaura, Stille, and Buchwald-Hartwig couplings. These reactions enable the introduction of diverse aryl or vinyl groups, facilitating the construction of novel heterocyclic compounds. Additionally, the aldehyde functionality at the 5-position allows for condensation reactions with various nucleophiles, including amines and hydrazines, leading to the formation of imines, imidazoles, and other nitrogen-containing heterocycles.

In the realm of pharmaceutical research, 2-Bromopyrimidine-5-carbaldehyde has been explored as a precursor for developing small-molecule inhibitors targeting various biological pathways. Pyrimidine derivatives are well-documented for their pharmacological activity, with many exhibiting antimicrobial, antiviral, anticancer, and anti-inflammatory properties. The aldehyde group in 2-Bromopyrimidine-5-carbaldehyde serves as a key moiety for generating covalent bonds with biological targets, enhancing drug binding affinity and efficacy. Recent studies have highlighted its role in synthesizing kinase inhibitors, which are critical in treating cancers and inflammatory diseases.

One notable application of 2-Bromopyrimidine-5-carbaldehyde is in the development of antiviral agents. The pyrimidine scaffold is structurally analogous to nucleobases found in DNA and RNA, making it a natural candidate for interfering with viral replication cycles. Researchers have leveraged the reactivity of 2-Bromopyrimidine-5-carbaldehyde to design molecules that inhibit viral polymerases or integrases. For instance, modifications at the 2- and 5-positions have been strategically employed to optimize binding interactions with viral enzymes while minimizing off-target effects.

The compound has also found utility in materials science, particularly in the synthesis of organic semiconductors and light-emitting diodes (OLEDs). Pyrimidine-based polymers and small molecules exhibit excellent optoelectronic properties due to their rigid aromatic structure and tunable electronic characteristics. By incorporating 2-Bromopyrimidine-5-carbaldehyde into polymer backbones or as a monomer unit, researchers can fine-tune the energy levels and charge transport properties of these materials. This has led to advancements in flexible electronics, photovoltaic devices, and display technologies.

Recent advancements in computational chemistry have further enhanced the understanding of 2-Bromopyrimidine-5-carbaldehyde's reactivity and potential applications. Molecular modeling studies have predicted novel reaction pathways and optimized synthetic strategies for incorporating this intermediate into complex drug candidates. Additionally, high-throughput screening techniques have been employed to rapidly identify derivatives of 2-Bromopyrimidine-5-carbaldehyde with enhanced biological activity. These computational and experimental approaches collectively accelerate the discovery process in medicinal chemistry.

The safety profile of 2-Bromopyrimidine-5-carbaldehyde is another critical consideration in its industrial applications. While it is not classified as a hazardous substance under standard regulatory frameworks, proper handling procedures must be followed to prevent exposure risks. Personal protective equipment (PPE), such as gloves and safety goggles, should be used when handling this compound in laboratory or industrial settings. Furthermore, adequate ventilation systems are essential to minimize inhalation hazards during synthesis or scale-up operations.

In conclusion,2-Bromopyrimidine-5-carbaldehyde (CAS No. 1456863-37-8) is a multifaceted compound with broad applications in pharmaceuticals and materials science. Its unique structural features enable diverse functionalization strategies, making it an invaluable intermediate for drug discovery and material innovation. As research continues to uncover new synthetic pathways and biological applications,2-Bromopyrimidine-5-carbaldehyde is poised to remain a cornerstone in modern chemical synthesis.

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