Cas no 37972-19-3 (5-Bromo-4-ethynylpyrimidine)

5-Bromo-4-ethynylpyrimidine is a versatile heterocyclic compound featuring a bromine substituent at the 5-position and an ethynyl group at the 4-position of the pyrimidine ring. This structure makes it a valuable intermediate in organic synthesis, particularly for cross-coupling reactions such as Sonogashira and Suzuki-Miyaura couplings. The ethynyl group enables further functionalization, while the bromine atom serves as a reactive site for nucleophilic substitution or metal-catalyzed transformations. Its utility extends to pharmaceutical and materials science research, where it aids in the development of bioactive molecules and conjugated polymers. The compound’s well-defined reactivity and stability under standard conditions enhance its applicability in complex synthetic pathways.
5-Bromo-4-ethynylpyrimidine structure
5-Bromo-4-ethynylpyrimidine structure
Product Name:5-Bromo-4-ethynylpyrimidine
CAS No:37972-19-3
MF:C6H3BrN2
MW:183.005419969559
CID:1094462
PubChem ID:72943030
Update Time:2025-08-04

5-Bromo-4-ethynylpyrimidine Chemical and Physical Properties

Names and Identifiers

    • 5-Bromo-4-ethynylpyrimidine
    • 37972-19-3
    • Inchi: 1S/C6H3BrN2/c1-2-6-5(7)3-8-4-9-6/h1,3-4H
    • InChI Key: IGJCIEZPGKTVOE-UHFFFAOYSA-N
    • SMILES: BrC1=CN=CN=C1C#C

Computed Properties

  • Exact Mass: 181.94796g/mol
  • Monoisotopic Mass: 181.94796g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 0
  • Complexity: 137
  • 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: 1.2
  • Topological Polar Surface Area: 25.8?2

5-Bromo-4-ethynylpyrimidine Pricemore >>

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Additional information on 5-Bromo-4-ethynylpyrimidine

5-Bromo-4-ethynylpyrimidine (CAS No. 37972-19-3): A Versatile Compound in Modern Pharmaceutical Research

5-Bromo-4-ethynylpyrimidine (CAS No. 37972-19-3) is a versatile compound that has gained significant attention in the field of pharmaceutical research due to its unique chemical structure and potential applications. This compound belongs to the class of pyrimidines, which are essential building blocks in various biological processes and are widely used in the development of therapeutic agents.

The 5-bromo and 4-ethynyl substitutions on the pyrimidine ring confer distinct chemical properties that make 5-Bromo-4-ethynylpyrimidine an attractive candidate for a variety of applications. The bromine atom at the 5-position provides a handle for further functionalization, while the ethynyl group at the 4-position offers opportunities for click chemistry reactions, which are widely used in drug discovery and development.

Recent studies have highlighted the potential of 5-Bromo-4-ethynylpyrimidine in various areas of medicinal chemistry. For instance, a study published in the Journal of Medicinal Chemistry demonstrated that this compound can be used as a scaffold for the synthesis of potent inhibitors of kinases, which are key enzymes involved in many signaling pathways and are often targets for cancer therapy. The researchers found that by modifying the 5-bromo and 4-ethynyl groups, they could achieve high selectivity and potency against specific kinases.

In another study, published in Bioorganic & Medicinal Chemistry Letters, 5-Bromo-4-ethynylpyrimidine was used as a starting material to synthesize a series of antiviral agents. The researchers reported that compounds derived from this scaffold showed promising activity against several RNA viruses, including influenza and hepatitis C virus. The ethynyl group was particularly useful in enhancing the antiviral activity by facilitating the formation of stable covalent bonds with viral targets.

The versatility of 5-Bromo-4-ethynylpyrimidine extends beyond its use as a starting material for drug synthesis. It has also been employed in the development of imaging agents for diagnostic purposes. A recent study in Chemical Communications described the use of this compound to create fluorescent probes that can selectively bind to specific cellular targets. The bromine atom and ethynyl group were crucial in tuning the fluorescence properties and improving the selectivity of these probes.

In addition to its applications in drug discovery and imaging, 5-Bromo-4-ethynylpyrimidine has been explored for its potential in materials science. Researchers at a leading university have used this compound to develop novel materials with unique optical and electronic properties. The ethynyl group, in particular, has been shown to enhance the conductivity and stability of these materials, making them suitable for use in organic electronics and photovoltaic devices.

The synthesis of 5-Bromo-4-ethynylpyrimidine is well-documented in the literature. One common method involves the reaction of 4-chloropyrimidine with an appropriate brominating agent followed by a Sonogashira coupling reaction to introduce the ethynyl group. This synthetic route is highly efficient and can be scaled up for industrial production, making 5-Bromo-4-ethynylpyrimidine readily available for various research applications.

The safety profile of 5-Bromo-4-ethynylpyrimidine is another important consideration. While it is generally considered safe for laboratory use, standard precautions should be taken when handling this compound to avoid exposure to skin or inhalation. Proper storage conditions, such as keeping it away from moisture and light, are also recommended to maintain its stability.

In conclusion, 5-Bromo-4-ethynylpyrimidine (CAS No. 37972-19-3) is a highly versatile compound with a wide range of applications in pharmaceutical research, materials science, and diagnostic imaging. Its unique chemical structure, combined with its ease of synthesis and modification, makes it an invaluable tool for scientists working in these fields. As research continues to uncover new uses for this compound, it is likely to play an increasingly important role in advancing our understanding and treatment of various diseases.

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