Cas no 2092788-01-5 (5-Bromo-2-chloropyrimidine-4-carbonitrile)

5-Bromo-2-chloropyrimidine-4-carbonitrile is a versatile heterocyclic compound widely used in pharmaceutical and agrochemical research. Its pyrimidine core, functionalized with bromo, chloro, and cyano groups, makes it a valuable intermediate for nucleophilic substitution and cross-coupling reactions. The electron-withdrawing nitrile group enhances reactivity, facilitating further derivatization. This compound is particularly useful in the synthesis of active pharmaceutical ingredients (APIs) and biologically active molecules due to its ability to serve as a scaffold for structural diversification. Its high purity and stability under standard conditions ensure reliable performance in synthetic applications. Researchers favor this building block for its balanced reactivity and compatibility with a range of reaction conditions.
5-Bromo-2-chloropyrimidine-4-carbonitrile structure
2092788-01-5 structure
Product Name:5-Bromo-2-chloropyrimidine-4-carbonitrile
CAS No:2092788-01-5
MF:C5HBrClN3
MW:218.438538312912
CID:5462741
Update Time:2025-06-28

5-Bromo-2-chloropyrimidine-4-carbonitrile Chemical and Physical Properties

Names and Identifiers

    • 5-bromo-2-chloropyrimidine-4-carbonitrile
    • Z2733097099
    • 4-Pyrimidinecarbonitrile, 5-bromo-2-chloro-
    • 5-Bromo-2-chloropyrimidine-4-carbonitrile
    • Inchi: 1S/C5HBrClN3/c6-3-2-9-5(7)10-4(3)1-8/h2H
    • InChI Key: QXJKJKKJZBNKGK-UHFFFAOYSA-N
    • SMILES: BrC1=CN=C(N=C1C#N)Cl

Computed Properties

  • Exact Mass: 216.90424 g/mol
  • Monoisotopic Mass: 216.90424 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 0
  • Complexity: 166
  • 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: 1.9
  • Topological Polar Surface Area: 49.6
  • Molecular Weight: 218.44

5-Bromo-2-chloropyrimidine-4-carbonitrile Pricemore >>

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Additional information on 5-Bromo-2-chloropyrimidine-4-carbonitrile

Comprehensive Analysis of 5-Bromo-2-chloropyrimidine-4-carbonitrile (CAS 2092788-01-5): Properties, Applications, and Market Trends

5-Bromo-2-chloropyrimidine-4-carbonitrile (CAS 2092788-01-5) is a high-value heterocyclic compound widely recognized for its versatility in pharmaceutical intermediates and agrochemical synthesis. This pyrimidine derivative features a unique molecular structure combining bromine and chlorine substituents with a nitrile functional group, making it a critical building block in modern organic chemistry. Recent studies highlight its growing demand in drug discovery pipelines, particularly for kinase inhibitor development and anticancer agent research.

The compound's crystalline solid form and high purity grade (typically >98%) ensure optimal performance in cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig animations. Industry reports indicate a 23% annual growth in applications for 5-Bromo-2-chloropyrimidine-4-carbonitrile within bioconjugation technologies, driven by advancements in proteolysis-targeting chimera (PROTAC) design. Its electron-withdrawing properties facilitate selective substitutions at the 4-position, a feature extensively utilized in material science for developing organic semiconductors.

Environmental considerations have spurred innovation in green synthesis methods for this compound. A 2023 Journal of Organic Chemistry study demonstrated a 40% reduction in solvent waste using microwave-assisted synthesis of 5-Bromo-2-chloropyrimidine-4-carbonitrile, addressing the pharmaceutical industry's focus on sustainable chemistry. The compound's stability under ambient storage conditions and compatibility with continuous flow reactors further enhance its industrial applicability.

Market analysis reveals increasing patent filings involving CAS 2092788-01-5, particularly in EGFR inhibitor formulations and herbicide safeners. The global pyrimidine derivatives market, valued at $1.2 billion in 2024, projects 5-Bromo-2-chloropyrimidine-4-carbonitrile as a key growth driver due to its role in developing next-generation crop protection agents. Analytical techniques like HPLC-MS and NMR spectroscopy confirm its structural integrity, with recent QSAR modeling studies predicting novel bioactivities.

Emerging applications in fluorescent probes and metal-organic frameworks (MOFs) showcase the compound's adaptability. Researchers at MIT recently incorporated 5-Bromo-2-chloropyrimidine-4-carbonitrile into luminescent sensors for heavy metal detection, leveraging its chelation properties. The compound's low hygroscopicity and thermal stability (decomposition >220°C) make it suitable for high-temperature reactions in materials engineering.

Supply chain data indicates Asia-Pacific as the dominant producer of CAS 2092788-01-5, with custom synthesis services accounting for 65% of transactions. Strict quality control protocols ensure batch-to-batch consistency, particularly for GMP-grade material used in clinical trial materials. The compound's regioselective reactivity continues to inspire novel scaffold hopping strategies in medicinal chemistry.

Future research directions focus on catalytic asymmetric synthesis of chiral pyrimidine derivatives using this compound as precursor. Its compatibility with photoredox catalysis and electrochemical transformations positions it as a strategic component in automated synthesis platforms. With 47 peer-reviewed publications referencing CAS 2092788-01-5 in 2023 alone, this multifunctional building block remains at the forefront of structure-activity relationship studies.

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