Cas no 1160923-92-1 (4-Chloro-5-vinylnicotinonitrile)

4-Chloro-5-vinylnicotinonitrile is a versatile heterocyclic compound featuring a chloro-substituted pyridine core with a vinyl and nitrile functional group. Its unique structure makes it a valuable intermediate in organic synthesis, particularly in the development of pharmaceuticals and agrochemicals. The presence of both electron-withdrawing (chloro and nitrile) and electron-donating (vinyl) groups enhances its reactivity, enabling selective modifications for tailored applications. This compound is particularly useful in cross-coupling reactions and cyclization processes, offering synthetic flexibility. Its high purity and stability under standard conditions ensure reliable performance in research and industrial settings. Suitable for further functionalization, it serves as a key building block in medicinal chemistry and material science.
4-Chloro-5-vinylnicotinonitrile structure
1160923-92-1 structure
Product Name:4-Chloro-5-vinylnicotinonitrile
CAS No:1160923-92-1
MF:C8H5ClN2
MW:164.591700315475
CID:1081235
PubChem ID:68447128
Update Time:2025-06-13

4-Chloro-5-vinylnicotinonitrile Chemical and Physical Properties

Names and Identifiers

    • 4-Chloro-5-vinylnicotinonitrile
    • 4-chloro-5-ethenylpyridine-3-carbonitrile
    • SCHEMBL2934623
    • 1160923-92-1
    • Inchi: 1S/C8H5ClN2/c1-2-6-4-11-5-7(3-10)8(6)9/h2,4-5H,1H2
    • InChI Key: IAOCPQXAWJXUKZ-UHFFFAOYSA-N
    • SMILES: ClC1C(C#N)=CN=CC=1C=C

Computed Properties

  • Exact Mass: 164.0141259g/mol
  • Monoisotopic Mass: 164.0141259g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 194
  • 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: 2
  • Topological Polar Surface Area: 36.7?2

4-Chloro-5-vinylnicotinonitrile Pricemore >>

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Additional information on 4-Chloro-5-vinylnicotinonitrile

Introduction to 4-Chloro-5-vinylnicotinonitrile (CAS No. 1160923-92-1)

4-Chloro-5-vinylnicotinonitrile, identified by the Chemical Abstracts Service Number (CAS No.) 1160923-92-1, is a significant intermediate in the field of organic synthesis and pharmaceutical chemistry. This compound belongs to the class of nicotinonitrile derivatives, which have garnered considerable attention due to their diverse applications in medicinal chemistry and material science. The structural features of 4-Chloro-5-vinylnicotinonitrile, including the presence of both a chloro substituent and a vinyl group, make it a versatile building block for the synthesis of more complex molecules.

The chloro functional group at the 4-position and the vinyl group at the 5-position provide unique reactivity that allows for further functionalization through various chemical transformations. These include nucleophilic substitution reactions, cross-coupling reactions, and addition reactions, which are pivotal in constructing biologically active scaffolds. The compound's ability to undergo such modifications has made it a valuable reagent in the development of novel pharmaceuticals and agrochemicals.

In recent years, there has been a growing interest in nicotinonitrile derivatives due to their potential pharmacological properties. Studies have demonstrated that these compounds exhibit a range of biological activities, including antimicrobial, anti-inflammatory, and anticancer effects. The structural motif of 4-Chloro-5-vinylnicotinonitrile is particularly noteworthy because it can be modified to target specific biological pathways. For instance, modifications at the chloro and vinyl positions can alter the compound's interaction with biological targets, leading to enhanced efficacy or selectivity.

One of the most exciting developments in the field has been the application of 4-Chloro-5-vinylnicotinonitrile in drug discovery programs. Researchers have leveraged its structural flexibility to design molecules that interact with enzymes and receptors involved in disease mechanisms. For example, derivatives of this compound have shown promise in inhibiting kinases and other enzymes implicated in cancer progression. The ability to fine-tune the structure through strategic modifications has opened up new avenues for therapeutic intervention.

The synthesis of 4-Chloro-5-vinylnicotinonitrile itself is an intriguing aspect of organic chemistry. Traditional methods involve multi-step processes that often require careful optimization to achieve high yields and purity. However, advances in synthetic methodologies have enabled more efficient routes to this intermediate. Catalytic processes, for instance, have been employed to streamline the synthesis while maintaining high selectivity. These improvements not only reduce production costs but also make the compound more accessible for research and industrial applications.

The role of computational chemistry in understanding the reactivity of 4-Chloro-5-vinylnicotinonitrile cannot be overstated. Molecular modeling techniques have provided insights into how different substituents influence its behavior in chemical reactions. By predicting reaction outcomes before conducting experiments, researchers can save time and resources. Furthermore, computational studies have helped identify new synthetic strategies that might not be apparent through experimental alone.

Recent research has also highlighted the importance of green chemistry principles in the synthesis of intermediates like 4-Chloro-5-vinylnicotinonitrile. Efforts are underway to develop more environmentally friendly methods that minimize waste and reduce hazardous byproducts. Solvent-free reactions, for example, have been explored as an alternative to traditional solvent-based processes. Such innovations align with global efforts to promote sustainable chemical practices.

The pharmaceutical industry has been particularly keen on exploring novel derivatives of 4-Chloro-5-vinylnicotinonitrile due to their potential therapeutic benefits. Preclinical studies have shown that certain analogs exhibit significant activity against resistant strains of bacteria and viruses. This has spurred interest in developing new antibiotics and antiviral agents based on this scaffold. The versatility of 4-Chloro-5-vinylnicotinonitrile as a starting material makes it an attractive candidate for further exploration.

In conclusion, 4-Chloro-5-vinylnicotinonitrile (CAS No. 1160923-92-1) is a multifaceted compound with broad applications in synthetic chemistry and drug development. Its unique structural features enable diverse chemical transformations, making it a valuable intermediate for constructing complex molecules with potential pharmacological activity. As research continues to uncover new synthetic methods and biological applications, this compound is poised to play an increasingly important role in the future of medicinal chemistry.

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