Cas no 1160995-48-1 (4-Bromopyrimidine-2-carbonitrile)

4-Bromopyrimidine-2-carbonitrile is a versatile heterocyclic compound featuring a bromine substituent at the 4-position and a cyano group at the 2-position of the pyrimidine ring. This structure makes it a valuable intermediate in organic synthesis, particularly in pharmaceutical and agrochemical applications. The bromine moiety facilitates further functionalization via cross-coupling reactions, while the electron-withdrawing cyano group enhances reactivity in nucleophilic substitutions. Its high purity and stability under standard conditions ensure reliable performance in complex transformations. The compound is commonly employed in the preparation of biologically active molecules, including kinase inhibitors and other therapeutic agents, due to its well-defined reactivity profile and compatibility with diverse synthetic routes.
4-Bromopyrimidine-2-carbonitrile structure
1160995-48-1 structure
Product Name:4-Bromopyrimidine-2-carbonitrile
CAS No:1160995-48-1
MF:C5H2BrN3
MW:183.993479251862
MDL:MFCD12400798
CID:1068160
PubChem ID:53407910
Update Time:2025-11-02

4-Bromopyrimidine-2-carbonitrile Chemical and Physical Properties

Names and Identifiers

    • 4-Bromopyrimidine-2-carbonitrile
    • 4-Bromo-pyrimidine-2-carbonitrile
    • Z1201626471
    • 1160995-48-1
    • SCHEMBL3632318
    • A893618
    • IPBOWNBJKYDXQB-UHFFFAOYSA-N
    • AKOS006240729
    • MB11791
    • EN300-217582
    • 4-bromo-2-cyanopyrimidine
    • MFCD12400798
    • FT-0750282
    • 2-Pyrimidinecarbonitrile, 4-bromo-
    • DTXSID80696102
    • CS-0341607
    • AS-32729
    • DA-15160
    • MDL: MFCD12400798
    • Inchi: 1S/C5H2BrN3/c6-4-1-2-8-5(3-7)9-4/h1-2H
    • InChI Key: IPBOWNBJKYDXQB-UHFFFAOYSA-N
    • SMILES: BrC1C=CN=C(C#N)N=1

Computed Properties

  • Exact Mass: 182.943
  • Monoisotopic Mass: 182.943
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 0
  • Complexity: 138
  • 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
  • Topological Polar Surface Area: 49.6A^2
  • XLogP3: 1.3

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Additional information on 4-Bromopyrimidine-2-carbonitrile

4-Bromopyrimidine-2-carbonitrile (CAS 1160995-48-1): A Versatile Building Block in Pharmaceutical and Material Sciences

4-Bromopyrimidine-2-carbonitrile (CAS 1160995-48-1) is a highly valuable heterocyclic compound that has gained significant attention in recent years due to its versatile applications in pharmaceutical research and material science. This brominated pyrimidine derivative serves as a crucial building block for the synthesis of various biologically active molecules and functional materials.

The molecular structure of 4-Bromopyrimidine-2-carbonitrile features a pyrimidine ring substituted with a bromine atom at the 4-position and a cyano group at the 2-position. This unique arrangement makes it an excellent substrate for nucleophilic aromatic substitution reactions and cross-coupling reactions, which are fundamental transformations in modern organic synthesis.

In pharmaceutical applications, 4-Bromopyrimidine-2-carbonitrile has become increasingly important as researchers explore new treatments for various diseases. Recent studies have shown its potential in developing kinase inhibitors, which are crucial for cancer therapy. The compound's ability to serve as a precursor for modified nucleoside analogs has also attracted attention in antiviral drug development, particularly in the context of emerging viral infections.

The material science field has benefited from 4-Bromopyrimidine-2-carbonitrile as well. Its incorporation into organic electronic materials has shown promise for developing more efficient organic light-emitting diodes (OLEDs) and organic photovoltaics. The compound's electron-withdrawing properties make it particularly valuable for tuning the electronic characteristics of π-conjugated systems.

From a synthetic chemistry perspective, 4-Bromopyrimidine-2-carbonitrile offers several advantages. The bromine atom serves as an excellent leaving group for palladium-catalyzed cross-coupling reactions, while the cyano group can be transformed into various functional groups or serve as a hydrogen bond acceptor. This dual functionality makes the compound a versatile intermediate for constructing complex molecular architectures.

Recent advancements in flow chemistry and continuous processing have opened new possibilities for the efficient production and utilization of 4-Bromopyrimidine-2-carbonitrile. These technologies address the growing demand for sustainable and scalable synthetic methods in the chemical industry.

The stability and storage requirements of 4-Bromopyrimidine-2-carbonitrile are important considerations for researchers and manufacturers. Proper handling under inert atmosphere and storage at controlled temperatures can significantly extend the compound's shelf life and maintain its reactivity for subsequent transformations.

Analytical characterization of 4-Bromopyrimidine-2-carbonitrile typically involves a combination of techniques including nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, and high-performance liquid chromatography (HPLC). These methods ensure the purity and identity of the compound, which is critical for its applications in sensitive research areas.

As the demand for specialty chemicals continues to grow in pharmaceutical and material science research, 4-Bromopyrimidine-2-carbonitrile maintains its position as an important synthetic intermediate. Its unique combination of reactivity and stability makes it particularly valuable for researchers developing new drugs and advanced materials.

The global market for pyrimidine derivatives like 4-Bromopyrimidine-2-carbonitrile has seen steady growth, driven by increasing research activities in medicinal chemistry and materials science. Manufacturers continue to optimize production processes to meet the growing demand while maintaining high purity standards.

Future research directions involving 4-Bromopyrimidine-2-carbonitrile may include its application in metal-organic frameworks (MOFs) and other advanced materials, as well as its potential in developing novel therapeutic agents. The compound's versatility ensures it will remain a valuable tool for chemists across multiple disciplines.

For researchers working with 4-Bromopyrimidine-2-carbonitrile, understanding its reactivity patterns and potential side reactions is crucial for successful synthetic applications. Recent literature provides valuable insights into optimizing reaction conditions and exploring new transformations involving this important building block.

In conclusion, 4-Bromopyrimidine-2-carbonitrile (CAS 1160995-48-1) represents a significant compound in modern chemical research. Its applications span from pharmaceutical development to advanced materials, making it an essential component in the toolkit of synthetic chemists. As research in these fields continues to advance, the importance of this bromopyrimidine derivative is likely to grow even further.

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