Cas no 54226-45-8 (2-(5,6-dichloropyridin-3-yl)acetonitrile)

2-(5,6-Dichloropyridin-3-yl)acetonitrile is a versatile organic intermediate primarily used in pharmaceutical and agrochemical synthesis. Its dichloropyridine backbone enhances reactivity, making it valuable for constructing complex heterocyclic compounds. The nitrile group offers further functionalization potential through hydrolysis, reduction, or cyclization reactions. This compound exhibits high purity and stability under standard storage conditions, ensuring consistent performance in multi-step synthetic routes. Its structural features make it particularly useful in the development of active ingredients for crop protection and medicinal applications. The precise substitution pattern on the pyridine ring allows for selective modifications, facilitating tailored molecular designs in research and industrial settings.
2-(5,6-dichloropyridin-3-yl)acetonitrile structure
54226-45-8 structure
Product Name:2-(5,6-dichloropyridin-3-yl)acetonitrile
CAS No:54226-45-8
MF:C7H4Cl2N2
MW:187.026059150696
CID:4029169
PubChem ID:20483532
Update Time:2025-05-27

2-(5,6-dichloropyridin-3-yl)acetonitrile Chemical and Physical Properties

Names and Identifiers

    • 3-Pyridineacetonitrile, 5,6-dichloro-
    • 2-(5,6-dichloropyridin-3-yl)acetonitrile
    • SCHEMBL1141731
    • AKOS026730105
    • EN300-134076
    • 54226-45-8
    • ECA22645
    • 843-997-5
    • Inchi: 1S/C7H4Cl2N2/c8-6-3-5(1-2-10)4-11-7(6)9/h3-4H,1H2
    • InChI Key: WQZMGKXBEWNAFP-UHFFFAOYSA-N
    • SMILES: ClC1=C(N=CC(CC#N)=C1)Cl

Computed Properties

  • Exact Mass: 185.9751535g/mol
  • Monoisotopic Mass: 185.9751535g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 175
  • 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: 2.1
  • Topological Polar Surface Area: 36.7?2

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Additional information on 2-(5,6-dichloropyridin-3-yl)acetonitrile

Research Brief on 3-Pyridineacetonitrile, 5,6-dichloro- (CAS: 54226-45-8) in Chemical Biology and Pharmaceutical Applications

3-Pyridineacetonitrile, 5,6-dichloro- (CAS: 54226-45-8) is a chlorinated pyridine derivative that has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound, characterized by its nitrile and dichloro-substituted pyridine ring, serves as a key intermediate in the synthesis of bioactive molecules, including kinase inhibitors and antiviral agents. Recent studies have highlighted its potential in drug discovery, particularly in targeting protein-protein interactions and modulating enzymatic activity.

A 2023 study published in the Journal of Medicinal Chemistry explored the use of 3-Pyridineacetonitrile, 5,6-dichloro- as a scaffold for developing selective kinase inhibitors. The research team employed structure-activity relationship (SAR) analysis to optimize the compound's binding affinity for specific kinase targets, demonstrating its efficacy in inhibiting aberrant signaling pathways associated with cancer. The study reported a 40% improvement in inhibitory potency compared to earlier analogs, underscoring the compound's potential in oncology therapeutics.

In addition to its role in kinase inhibition, recent investigations have revealed the compound's utility in antiviral drug development. A 2024 preprint in BioRxiv detailed its incorporation into nucleoside analogs, where it exhibited promising activity against RNA viruses, including SARS-CoV-2 variants. The dichloro-substitution was found to enhance metabolic stability, addressing a common limitation in antiviral prodrug design. These findings position 3-Pyridineacetonitrile, 5,6-dichloro- as a valuable building block for next-generation antiviral agents.

From a synthetic chemistry perspective, advancements in the scalable production of 3-Pyridineacetonitrile, 5,6-dichloro- have been reported in Organic Process Research & Development (2023). Researchers developed a novel catalytic system using palladium nanoparticles, achieving an 85% yield with reduced environmental impact compared to traditional methods. This breakthrough addresses supply chain challenges for pharmaceutical manufacturers relying on this intermediate.

Ongoing clinical trials (Phase I/II) are evaluating derivatives of 3-Pyridineacetonitrile, 5,6-dichloro- as potential treatments for neurodegenerative diseases. Preliminary data presented at the 2024 American Chemical Society meeting suggests these compounds can cross the blood-brain barrier and exhibit neuroprotective effects in animal models of Parkinson's disease. The mechanism appears to involve modulation of mitochondrial function and reduction of oxidative stress.

Future research directions for 3-Pyridineacetonitrile, 5,6-dichloro- include exploration of its chiral derivatives for asymmetric synthesis applications and investigation of its photophysical properties for biosensing applications. The compound's unique electronic configuration, resulting from the electron-withdrawing chloro and nitrile groups, makes it particularly interesting for materials science applications in organic electronics.

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