Cas no 1163707-56-9 (1-(4-bromopyridin-2-yl)cyclopropane-1-carbonitrile)

1-(4-Bromopyridin-2-yl)cyclopropane-1-carbonitrile is a versatile brominated pyridine derivative featuring a cyclopropane-carbonitrile moiety. This compound serves as a valuable intermediate in organic synthesis, particularly in pharmaceutical and agrochemical applications, due to its reactive 4-bromopyridyl group and sterically constrained cyclopropane ring. The presence of both electron-withdrawing (bromine and nitrile) and rigid structural components enhances its utility in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, enabling efficient derivatization. Its stability and well-defined reactivity profile make it suitable for constructing complex heterocyclic frameworks. The compound is typically handled under inert conditions to preserve its integrity.
1-(4-bromopyridin-2-yl)cyclopropane-1-carbonitrile structure
1163707-56-9 structure
Product Name:1-(4-bromopyridin-2-yl)cyclopropane-1-carbonitrile
CAS No:1163707-56-9
MF:C9H7BrN2
MW:223.069280862808
MDL:MFCD13191450
CID:1035782
PubChem ID:57417093
Update Time:2025-11-02

1-(4-bromopyridin-2-yl)cyclopropane-1-carbonitrile Chemical and Physical Properties

Names and Identifiers

    • 1-(4-Bromopyridin-2-yl)cyclopropanecarbonitrile
    • 1-(4-bromopyridin-2-yl)cyclopropane-1-carbonitrile
    • AB90891
    • 1-(4-bromo-pyridin-2-yl)-cyclopropanecarbonitrile
    • DTXSID90726262
    • AKOS016000483
    • SCHEMBL1938995
    • A905441
    • 1163707-56-9
    • Cyclopropanecarbonitrile, 1-(4-bromo-2-pyridinyl)-
    • CS-0079208
    • EN300-3221942
    • MDMVBPTVKDMKFG-UHFFFAOYSA-N
    • DB-362853
    • MDL: MFCD13191450
    • Inchi: 1S/C9H7BrN2/c10-7-1-4-12-8(5-7)9(6-11)2-3-9/h1,4-5H,2-3H2
    • InChI Key: MDMVBPTVKDMKFG-UHFFFAOYSA-N
    • SMILES: BrC1C=CN=C(C=1)C1(C#N)CC1

Computed Properties

  • Exact Mass: 221.97926g/mol
  • Monoisotopic Mass: 221.97926g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 226
  • 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: 1.6
  • Topological Polar Surface Area: 36.7?2

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1-(4-bromopyridin-2-yl)cyclopropane-1-carbonitrile Related Literature

Additional information on 1-(4-bromopyridin-2-yl)cyclopropane-1-carbonitrile

1-(4-Bromopyridin-2-yl)cyclopropane-1-carbonitrile (CAS 1163707-56-9): A Versatile Building Block in Modern Organic Synthesis

1-(4-Bromopyridin-2-yl)cyclopropane-1-carbonitrile (CAS 1163707-56-9) is an increasingly important heterocyclic compound that has gained significant attention in pharmaceutical research and material science. This bromopyridine derivative with its unique cyclopropane-carbonitrile structure serves as a valuable chemical intermediate for various synthetic applications.

The molecular structure of 1-(4-bromopyridin-2-yl)cyclopropane-1-carbonitrile combines three key functional elements: a pyridine ring, a cyclopropane moiety, and a nitrile group. This combination creates a versatile scaffold that can participate in numerous cross-coupling reactions, making it particularly valuable in medicinal chemistry for drug discovery programs. The bromine substituent at the 4-position of the pyridine ring offers an excellent handle for palladium-catalyzed reactions, while the cyclopropane-carbonitrile unit provides opportunities for further structural elaboration.

Recent trends in organic synthesis have highlighted the growing demand for 1-(4-bromopyridin-2-yl)cyclopropane-1-carbonitrile as researchers explore novel small molecule therapeutics. The compound's ability to serve as a precursor for kinase inhibitors and other biologically active compounds has made it particularly relevant in addressing current challenges in drug development. Many researchers are searching for information about "synthesis of bromopyridine derivatives" or "applications of cyclopropane-carbonitrile compounds," reflecting the scientific community's interest in this chemical space.

In material science applications, 1-(4-bromopyridin-2-yl)cyclopropane-1-carbonitrile has shown promise as a building block for organic electronic materials. Its rigid cyclopropane structure and electron-withdrawing nitrile group can influence the electronic properties of resulting materials, making it interesting for OLED development and organic semiconductors. The compound's thermal stability and synthetic versatility contribute to its utility in these advanced applications.

The synthesis of 1-(4-bromopyridin-2-yl)cyclopropane-1-carbonitrile typically involves palladium-catalyzed cross-coupling strategies or nucleophilic substitution reactions starting from appropriate pyridine precursors. Modern synthetic approaches focus on improving atom economy and reaction efficiency, addressing common search queries like "green synthesis of heterocyclic nitriles" or "optimized routes to bromopyridine derivatives." These developments align with the growing emphasis on sustainable chemistry practices in the pharmaceutical industry.

Analytical characterization of 1-(4-bromopyridin-2-yl)cyclopropane-1-carbonitrile typically employs standard techniques including NMR spectroscopy, mass spectrometry, and HPLC analysis. The compound's purity is particularly important for its applications in high-value chemical synthesis, with many researchers searching for "analytical methods for nitrile-containing compounds" to ensure quality control in their work.

The commercial availability of 1-(4-bromopyridin-2-yl)cyclopropane-1-carbonitrile has increased in recent years to meet growing demand from both academic research and industrial applications. Suppliers often highlight its use as a pharmaceutical intermediate or material science precursor, responding to market needs for specialized chemical building blocks. Current pricing trends reflect its status as a high-value specialty chemical with applications in cutting-edge research areas.

Looking forward, 1-(4-bromopyridin-2-yl)cyclopropane-1-carbonitrile is expected to maintain its importance in organic synthesis as researchers continue to explore its potential in drug discovery and advanced materials. The compound's unique structural features and synthetic flexibility position it well to address emerging challenges in these fields, making it a subject of ongoing scientific interest and commercial development.

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