Cas no 117571-49-0 (4-(4-Benzyloxyphenyl)benzonitrile)

4-(4-Benzyloxyphenyl)benzonitrile is a synthetic organic compound featuring a benzonitrile core substituted with a benzyloxyphenyl group. This structure imparts unique electronic and steric properties, making it valuable as an intermediate in pharmaceutical and materials chemistry. Its aromatic and polar nitrile functionality enhances reactivity in cross-coupling reactions, facilitating the synthesis of complex molecules. The benzyloxy group offers additional versatility for further functionalization or deprotection under mild conditions. With high purity and stability, this compound is well-suited for research applications requiring precise molecular scaffolds. Its consistent performance and compatibility with diverse reaction conditions make it a reliable choice for advanced synthetic workflows.
4-(4-Benzyloxyphenyl)benzonitrile structure
117571-49-0 structure
Product Name:4-(4-Benzyloxyphenyl)benzonitrile
CAS No:117571-49-0
MF:C20H15NO
MW:285.339205026627
MDL:MFCD06802283
CID:131567
PubChem ID:20099933
Update Time:2025-05-20

4-(4-Benzyloxyphenyl)benzonitrile Chemical and Physical Properties

Names and Identifiers

    • 4'-(Benzyloxy)-[1,1'-biphenyl]-4-carbonitrile
    • [1,1'-Biphenyl]-4-carbonitrile,4'-(phenylmethoxy)-
    • 4-(4-phenylmethoxyphenyl)benzonitrile
    • 4'-BENZYLOXY-4-CYANO-1,1'-BIPHENYL
    • Benzyloxycyanobiphenyl
    • BB 0223334
    • 4 inverted exclamation marka-(Phenylmethoxy)[1,1 inverted exclamation marka-biphenyl]-4-carbonitrile
    • 4'-(Benzyloxy)[1,1'-biphenyl]-4-carbonitrile
    • 4'-Benzyloxy-biphenyl-4-carbonitrile
    • AKOS004116161
    • CS-0210573
    • 4-(4-Benzyloxyphenyl)benzonitrile
    • 117571-49-0
    • MFCD06802283
    • BS-26092
    • DTXSID10602453
    • GFKDFMBBVRNDIQ-UHFFFAOYSA-N
    • 4-benzyloxy-4'-bi-phenylcarbonitrile
    • SCHEMBL7372943
    • 4-benzyloxy-4'-biphenylcarbonitrile
    • MDL: MFCD06802283
    • Inchi: 1S/C20H15NO/c21-14-16-6-8-18(9-7-16)19-10-12-20(13-11-19)22-15-17-4-2-1-3-5-17/h1-13H,15H2
    • InChI Key: GFKDFMBBVRNDIQ-UHFFFAOYSA-N
    • SMILES: O(CC1C=CC=CC=1)C1C=CC(=CC=1)C1C=CC(C#N)=CC=1

Computed Properties

  • Exact Mass: 285.11545
  • Monoisotopic Mass: 285.115364102g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 22
  • Rotatable Bond Count: 4
  • Complexity: 362
  • 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: 5.1
  • Topological Polar Surface Area: 33?2

Experimental Properties

  • PSA: 33.02

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Additional information on 4-(4-Benzyloxyphenyl)benzonitrile

Professional Introduction to 4-(4-Benzyloxyphenyl)benzonitrile (CAS No. 117571-49-0)

4-(4-Benzyloxyphenyl)benzonitrile, with the chemical formula C21H17NO, is a significant compound in the field of pharmaceutical chemistry and organic synthesis. This compound is characterized by its unique structural features, which include a benzonitrile moiety linked to a phenyl ring that is further substituted with a benzyloxy group. The presence of these functional groups makes it a versatile intermediate in the synthesis of various bioactive molecules.

The CAS number 117571-49-0 provides a unique identifier for this compound, ensuring accurate classification and referencing in scientific literature and industrial applications. The benzonitrile group is known for its ability to participate in nucleophilic addition reactions, while the benzyloxy group introduces hydrophobicity and can serve as a protecting group in synthetic pathways. These properties make 4-(4-Benzyloxyphenyl)benzonitrile a valuable building block in the development of new pharmaceuticals.

In recent years, there has been growing interest in the application of 4-(4-Benzyloxyphenyl)benzonitrile in medicinal chemistry. Its structural framework is conducive to the design of molecules with potential therapeutic effects. For instance, derivatives of this compound have been explored as inhibitors of enzymes involved in inflammatory pathways. The benzyloxyphenyl moiety, in particular, has shown promise in modulating the activity of targets such as kinases and phosphodiesterases, which are crucial in various disease mechanisms.

One of the most compelling aspects of 4-(4-Benzyloxyphenyl)benzonitrile is its role in the synthesis of small-molecule drugs. Researchers have leveraged its reactivity to develop novel compounds that exhibit improved pharmacokinetic properties compared to existing therapies. The benzonitrile group can be further functionalized to introduce additional substituents, allowing for fine-tuning of biological activity. This flexibility has led to several patents and ongoing clinical trials investigating the efficacy of molecules derived from this scaffold.

The pharmaceutical industry has also recognized the potential of 4-(4-Benzyloxyphenyl)benzonitrile in drug discovery programs. Its incorporation into libraries of compounds has facilitated high-throughput screening processes aimed at identifying new lead candidates. The compound’s ability to undergo cross-coupling reactions, such as Suzuki-Miyaura coupling, further enhances its utility as a synthetic intermediate. These reactions enable the rapid assembly of complex molecular structures, which would be otherwise challenging to achieve through traditional synthetic methods.

Recent advancements in computational chemistry have also highlighted the significance of 4-(4-Benzyloxyphenyl)benzonitrile in drug design. Molecular modeling studies have demonstrated that modifications to its structure can influence binding affinity and selectivity towards biological targets. This has spurred interest in developing computational tools that predict the behavior of such compounds before experimental synthesis. Such innovations are expected to accelerate the drug development pipeline and reduce costs associated with traditional trial-and-error approaches.

The long-tail keyword "synthesis of 4-(4-Benzyloxyphenyl)benzonitrile" underscores its importance as a synthetic intermediate. The compound’s accessibility through multi-step organic synthesis routes has made it a preferred choice for researchers aiming to explore novel chemical entities. Its stability under various reaction conditions further enhances its appeal, ensuring consistent yields and purity levels required for pharmaceutical applications.

In conclusion, 4-(4-Benzyloxyphenyl)benzonitrile (CAS No. 117571-49-0) represents a cornerstone in modern pharmaceutical chemistry. Its unique structural attributes and reactivity profile make it an indispensable tool for medicinal chemists seeking to develop innovative therapeutic agents. As research continues to uncover new applications for this compound, its significance in drug discovery is likely to grow even further.

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