Cas no 778646-96-1 (4-(4-Bromophenyl)-2-(methylthio)pyrimidine)

4-(4-Bromophenyl)-2-(methylthio)pyrimidine is a brominated pyrimidine derivative featuring a methylthio substituent at the 2-position. This compound serves as a versatile intermediate in organic synthesis, particularly in the development of pharmaceuticals, agrochemicals, and functional materials. The bromophenyl group enhances reactivity for cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, enabling further structural diversification. The methylthio moiety offers additional functionalization potential through oxidation or nucleophilic substitution. Its well-defined structure and high purity make it suitable for precise synthetic applications. The compound’s stability under standard conditions ensures reliable handling and storage, supporting its use in research and industrial processes.
4-(4-Bromophenyl)-2-(methylthio)pyrimidine structure
778646-96-1 structure
Product Name:4-(4-Bromophenyl)-2-(methylthio)pyrimidine
CAS No:778646-96-1
MF:C11H9BrN2S
MW:281.171560049057
CID:1029366
PubChem ID:57936294
Update Time:2025-05-22

4-(4-Bromophenyl)-2-(methylthio)pyrimidine Chemical and Physical Properties

Names and Identifiers

    • 4-(4-Bromophenyl)-2-(methylthio)pyrimidine
    • 4-(4-bromophenyl)-2-methylsulfanylpyrimidine
    • GNSLWJAFESZPBJ-UHFFFAOYSA-N
    • AKOS022171850
    • 3-PYRIDINEACETICACID,A-OXO,ETHYLESTER
    • 4-(4-Bromophenyl)-2-(methylsulfanyl)pyrimidine
    • A848248
    • SCHEMBL4487034
    • FT-0713931
    • 778646-96-1
    • DTXSID30728321
    • 4-(4-Bromo-phenyl)-2-methylsulfanyl-pyrimidine
    • SB60273
    • DA-22585
    • Inchi: 1S/C11H9BrN2S/c1-15-11-13-7-6-10(14-11)8-2-4-9(12)5-3-8/h2-7H,1H3
    • InChI Key: GNSLWJAFESZPBJ-UHFFFAOYSA-N
    • SMILES: BrC1C=CC(=CC=1)C1C=CN=C(N=1)SC

Computed Properties

  • Exact Mass: 279.96698g/mol
  • Monoisotopic Mass: 279.96698g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 2
  • Complexity: 195
  • 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: 3.4
  • Topological Polar Surface Area: 51.1?2

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Additional information on 4-(4-Bromophenyl)-2-(methylthio)pyrimidine

4-(4-Bromophenyl)-2-(methylthio)pyrimidine: A Comprehensive Overview

The compound 4-(4-Bromophenyl)-2-(methylthio)pyrimidine, identified by the CAS number 778646-96-1, is a heterocyclic aromatic compound with significant potential in various chemical and pharmaceutical applications. This molecule belongs to the class of pyrimidines, which are six-membered rings containing two nitrogen atoms at positions 1 and 3. The substitution pattern of this compound includes a bromophenyl group at position 4 and a methylthio group at position 2, making it a unique derivative with distinct chemical properties.

The synthesis of 4-(4-Bromophenyl)-2-(methylthio)pyrimidine typically involves multi-step reactions, often starting from basic pyrimidine precursors. Recent advancements in synthetic chemistry have enabled the development of more efficient and environmentally friendly methods for its production. For instance, researchers have explored the use of microwave-assisted synthesis and catalytic systems to optimize reaction conditions, reducing both time and energy consumption. These methods not only enhance the yield but also improve the purity of the final product, making it more suitable for high-quality applications.

The structural features of 4-(4-Bromophenyl)-2-(methylthio)pyrimidine contribute to its unique electronic properties. The methylthio group at position 2 introduces electron-donating effects, which can influence the reactivity of the molecule in various chemical reactions. This property has been leveraged in recent studies to explore its potential as a building block in medicinal chemistry. For example, this compound has been investigated as a lead molecule for the development of new drug candidates targeting specific biological pathways.

In terms of applications, 4-(4-Bromophenyl)-2-(methylthio)pyrimidine has shown promise in the field of pharmacology. Its ability to interact with specific biological targets makes it a valuable tool in drug discovery programs. Recent research has focused on its potential as an anti-inflammatory agent, where it has demonstrated moderate activity in inhibiting key enzymes involved in inflammatory processes. Additionally, studies have explored its role as an antimicrobial agent, particularly against gram-positive bacteria, highlighting its potential in developing new antibiotics.

The bromophenyl substituent at position 4 plays a crucial role in modulating the physical and chemical properties of this compound. Bromine's electron-withdrawing effects can influence the molecule's solubility, stability, and reactivity. These characteristics are particularly important when considering its use in pharmaceutical formulations, where bioavailability and shelf life are critical factors. Recent studies have also examined the impact of this substituent on the compound's photostability, which is essential for applications involving light-sensitive systems.

The methylthio group at position 2 adds another layer of complexity to this molecule's behavior. This group is known for its ability to participate in sulfur-based interactions, which can be exploited in designing drugs that target specific protein pockets or enzyme active sites. Recent computational studies have provided insights into how this group interacts with biological molecules at the molecular level, offering valuable information for rational drug design.

In conclusion, 4-(4-Bromophenyl)-2-(methylthio)pyrimidine, with its unique structural features and versatile properties, continues to be an area of active research across multiple disciplines. Its potential applications span from materials science to pharmacology, making it a valuable compound for both academic and industrial settings. As research progresses, further insights into its properties and functionalities are expected to unlock new opportunities for its utilization.

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