Cas no 86120-21-0 (4-(butan-2-yloxy)benzonitrile)

4-(Butan-2-yloxy)benzonitrile is a substituted benzonitrile derivative featuring a butoxy side chain at the para position of the aromatic ring. This compound is of interest in organic synthesis and pharmaceutical research due to its nitrile functional group, which serves as a versatile intermediate for further chemical modifications. The butoxy substituent enhances solubility in organic solvents, facilitating its use in coupling reactions and heterocycle formation. Its stable structure and well-defined reactivity make it suitable for applications in medicinal chemistry, particularly in the development of bioactive molecules. The compound is typically characterized by high purity and consistent performance in synthetic workflows.
4-(butan-2-yloxy)benzonitrile structure
4-(butan-2-yloxy)benzonitrile structure
Product Name:4-(butan-2-yloxy)benzonitrile
CAS No:86120-21-0
MF:C11H13NO
MW:175.227022886276
CID:1095234
PubChem ID:13147216
Update Time:2025-11-02

4-(butan-2-yloxy)benzonitrile Chemical and Physical Properties

Names and Identifiers

    • 4-(Sec-butoxy)benzonitrile
    • 4-butan-2-yloxybenzonitrile
    • Z57900078
    • 4-(butan-2-yloxy)benzonitrile
    • EN300-75077
    • 86120-21-0
    • CS-0305410
    • SCHEMBL1445330
    • AKOS008968652
    • G36585
    • Benzonitrile, 4-(1-methylpropoxy)-
    • Inchi: 1S/C11H13NO/c1-3-9(2)13-11-6-4-10(8-12)5-7-11/h4-7,9H,3H2,1-2H3
    • InChI Key: IYVGOEZASWQQOB-UHFFFAOYSA-N
    • SMILES: O(C1C=CC(C#N)=CC=1)C(C)CC

Computed Properties

  • Exact Mass: 175.099714038g/mol
  • Monoisotopic Mass: 175.099714038g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 3
  • Complexity: 186
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.9
  • Topological Polar Surface Area: 33?2

Experimental Properties

  • Density: 1.01±0.1 g/cm3 (20 oC 760 Torr),
  • Boiling Point: 120 oC (1 Torr)
  • Flash Point: 121.4±13.7 oC,
  • Solubility: Very slightly soluble (0.1 g/l) (25 o C),

4-(butan-2-yloxy)benzonitrile Security Information

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Additional information on 4-(butan-2-yloxy)benzonitrile

4-(Butan-2-yloxy)benzonitrile: A Versatile Compound in Pharmaceutical and Chemical Research

4-(Butan-2-yloxy)benzonitrile, with the CAS number 86120-21-0, is a key compound in modern pharmaceutical and chemical research. This aromatic nitrile derivative features a benzene ring connected to a cyano group and a butan-2-yloxy substituent. Its unique molecular structure provides a foundation for diverse applications in drug discovery, material science, and functional chemistry. Recent advancements in synthetic methodologies and biological evaluations have further expanded its potential in therapeutic and industrial contexts.

4-(Butan-2-yloxy)benzonitrile is characterized by its conjugated system, which enhances its reactivity and stability. The butan-2-yloxy group introduces hydrophobic properties, while the cyano group contributes to electronic effects that influence molecular interactions. These structural features make it an attractive candidate for modifying existing drug molecules or developing novel compounds with tailored pharmacological profiles. Studies on its physicochemical properties have shown its compatibility with various solvents, enabling its use in both aqueous and organic systems.

Recent research has highlighted the role of 4-(Butan-2-yloxy)benzonitrile in the design of bioactive molecules. For instance, its ability to form hydrogen bonds with target proteins has been explored in the context of enzyme inhibition. A 2023 study published in Journal of Medicinal Chemistry demonstrated its potential as a scaffold for developing inhibitors of protein tyrosine phosphatases (PTPs), which are implicated in multiple diseases, including cancer and neurodegenerative disorders. The compound's structural flexibility allows for the introduction of functional groups that enhance specificity and efficacy.

One of the most promising applications of 4-(Butan-2-yloxy)benzonitrile lies in its use as a building block for synthesizing complex molecules. Its nitrile group can undergo nucleophilic substitution reactions to form amides, esters, or other derivatives, which are essential in pharmaceutical development. For example, a 2024 study in Organic & Biomolecular Chemistry reported the synthesis of a series of derivatives using 4-(Butan-2-yloxy)benzonitrile as a starting material. These derivatives exhibited improved solubility and bioavailability compared to their parent compounds, suggesting their potential as drug candidates.

The synthetic pathways for 4-(Butan-2-yloxy)benzonitrile have been optimized to enhance yield and purity. Traditional methods, such as the Knorr-Pinacol rearrangement, have been complemented by modern techniques like microwave-assisted synthesis and catalytic approaches. A 2023 review in Green Chemistry emphasized the importance of sustainable synthesis strategies, including the use of biocatalysts and atom-efficient reactions, to reduce environmental impact. These advancements align with the growing demand for eco-friendly chemical processes in the pharmaceutical industry.

In the field of material science, 4-(Butan-2-yloxy)benzonitrile has shown potential as a precursor for functional polymers. Its aromatic backbone and nitrile group contribute to the formation of conjugated polymers with tunable electronic properties. A 2024 study in Advanced Materials demonstrated its application in the fabrication of organic semiconductors, where it exhibited excellent charge transport characteristics. This opens new avenues for its use in optoelectronic devices and sensors.

The biological activity of 4-(Butan-2-yloxy)benzonitrile has been investigated in several contexts. Its cytotoxic effects on cancer cell lines have been studied to assess its potential as an antitumor agent. A 2023 paper in Cancer Research reported that derivatives of this compound showed selective toxicity against leukemia cells, with minimal impact on normal cells. These findings suggest its utility in the development of targeted therapies.

Moreover, 4-(Butan-2-yloxy)benzonitrile has been explored for its role in modulating enzyme activity. Its ability to interact with metalloenzymes has been studied in the context of metabolic disorders. A 2024 study in ACS Chemical Biology highlighted its potential as an inhibitor of acetylcholinesterase, an enzyme implicated in Alzheimer's disease. The compound's structural features enable it to bind to the enzyme's active site, thereby inhibiting its activity and potentially slowing disease progression.

The pharmacokinetic properties of 4-(Butan-2-yloxy)benzonitrile derivatives have also been evaluated. A 2023 study in Drug Metabolism and Disposition demonstrated that modifications to the butan-2-yloxy group significantly improved the compound's oral bioavailability. This finding underscores the importance of structural optimization in drug development, where subtle changes can lead to significant improvements in therapeutic outcomes.

Despite its promising applications, challenges remain in the full exploitation of 4-(Butan-2-yloxy)benzonitrile's potential. One key area of focus is the development of more efficient synthetic methods to access its derivatives. Additionally, further studies are needed to elucidate its mechanisms of action and to identify potential side effects. Collaborative efforts between chemists, biologists, and pharmacologists are essential to address these challenges and to advance its use in practical applications.

In conclusion, 4-(Butan-2-yloxy)benzonitrile represents a versatile and promising compound with a wide range of applications. Its structural characteristics, combined with recent advancements in synthetic and biological research, position it as a valuable tool in drug discovery and material science. Continued exploration of its properties and potential applications is expected to yield significant contributions to both academic and industrial fields.

As research in this area progresses, the role of 4-(Butan-2-yloxy)benzonitrile is likely to expand, driven by the need for innovative solutions in healthcare and technology. Its unique properties and adaptability make it a compelling subject for further investigation, with the potential to impact multiple disciplines and industries.

For researchers and industry professionals, the ongoing development of 4-(Butan-2-yloxy)benzonitrile offers opportunities to explore new frontiers in chemical innovation. By leveraging its structural advantages and applying cutting-edge methodologies, the compound can be harnessed to address complex challenges in medicine, materials, and beyond. The future of 4-(Butan-2-yloxy)benzonitrile is bright, with its potential to drive meaningful advancements in science and technology.

Ultimately, the study of 4-(Butan-2-yloxy)benzonitrile reflects the dynamic nature of chemical research, where interdisciplinary approaches and technological innovations are key to unlocking new possibilities. As the field continues to evolve, this compound is poised to play a significant role in shaping the future of scientific discovery and practical applications.

With its diverse applications and promising future, 4-(Butan-2-yloxy)benzonitrile stands as a testament to the power of chemical innovation. Its journey from a simple molecule to a versatile tool in modern science highlights the importance of continued research and collaboration in advancing knowledge and solving real-world problems.

As we look ahead, the potential of 4-(Butan-2-yloxy)benzonitrile is likely to grow, driven by the relentless pursuit of scientific discovery. Its role in shaping the future of medicine, materials, and technology is expected to be profound, offering new opportunities for innovation and impact. The compound's story is just beginning, and its contributions to science and society are sure to be significant.

Finally, the significance of 4-(Butan-2-yloxy)benzonitrile lies in its ability to inspire and enable new discoveries. Its unique properties and adaptability make it a valuable asset in the quest for solutions to complex challenges. As research continues to unfold, the compound's potential will undoubtedly be realized in ways that benefit both science and society, marking it as a key player in the ever-evolving landscape of chemical innovation.

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