Cas no 154188-73-5 ((5-aminopent-1-yn-1-yl)trimethylsilane)

(5-Aminopent-1-yn-1-yl)trimethylsilane is a functionalized alkyne derivative featuring both a terminal alkyne group protected by a trimethylsilyl (TMS) moiety and a primary amine group at the opposite end of the pentynyl chain. This bifunctional structure makes it a versatile intermediate in organic synthesis, particularly in click chemistry applications such as Cu-catalyzed azide-alkyne cycloadditions (CuAAC). The TMS group enhances stability and allows for selective deprotection under mild conditions, while the amine functionality offers further derivatization potential. Its well-defined reactivity and compatibility with various reaction conditions make it valuable for constructing complex molecular architectures in pharmaceuticals, materials science, and bioconjugation.
(5-aminopent-1-yn-1-yl)trimethylsilane structure
154188-73-5 structure
Product Name:(5-aminopent-1-yn-1-yl)trimethylsilane
CAS No:154188-73-5
MF:C8H17NSi
MW:155.312783002853
CID:3799522
Update Time:2025-05-27

(5-aminopent-1-yn-1-yl)trimethylsilane Chemical and Physical Properties

Names and Identifiers

    • 4-Pentyn-1-amine, 5-(trimethylsilyl)-
    • (5-aminopent-1-yn-1-yl)trimethylsilane
    • Inchi: 1S/C8H17NSi/c1-10(2,3)8-6-4-5-7-9/h4-5,7,9H2,1-3H3
    • InChI Key: DNFJAHRRHWZTFE-UHFFFAOYSA-N
    • SMILES: C(N)CCC#C[Si](C)(C)C

Experimental Properties

  • Density: 0.847±0.06 g/cm3(Predicted)
  • Boiling Point: 175.8±23.0 °C(Predicted)
  • pka: 9.99±0.10(Predicted)

(5-aminopent-1-yn-1-yl)trimethylsilane Pricemore >>

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Additional information on (5-aminopent-1-yn-1-yl)trimethylsilane

Recent Advances in the Application of (5-aminopent-1-yn-1-yl)trimethylsilane (CAS: 154188-73-5) in Chemical Biology and Pharmaceutical Research

The compound (5-aminopent-1-yn-1-yl)trimethylsilane (CAS: 154188-73-5) has recently garnered significant attention in the field of chemical biology and pharmaceutical research. This molecule, characterized by its terminal alkyne and amine functionalities, serves as a versatile building block in organic synthesis and bioconjugation strategies. Recent studies have highlighted its potential in the development of novel therapeutics, diagnostic tools, and chemical probes for biological systems.

One of the most notable applications of (5-aminopent-1-yn-1-yl)trimethylsilane is its role in click chemistry, particularly in copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. The terminal alkyne group facilitates efficient conjugation with azide-containing molecules, enabling the synthesis of complex biomolecules with high specificity. Recent research has demonstrated its utility in the labeling of proteins, nucleic acids, and small molecules, thereby enhancing the study of biological processes at the molecular level.

In the context of drug discovery, (5-aminopent-1-yn-1-yl)trimethylsilane has been employed as a key intermediate in the synthesis of pharmacologically active compounds. For instance, it has been used to develop novel kinase inhibitors and antimicrobial agents. A 2023 study published in the Journal of Medicinal Chemistry reported the successful incorporation of this compound into a series of potent inhibitors targeting tyrosine kinases, which are implicated in various cancers. The study underscored the compound's role in improving the pharmacokinetic properties of the inhibitors, such as solubility and bioavailability.

Beyond its applications in drug development, (5-aminopent-1-yn-1-yl)trimethylsilane has also been explored in the field of chemical biology for the design of activity-based probes (ABPs). These probes enable the real-time monitoring of enzyme activity in living systems, providing valuable insights into disease mechanisms. A recent study in ACS Chemical Biology utilized this compound to develop a probe for detecting caspase activity, a critical mediator of apoptosis. The probe exhibited high sensitivity and selectivity, making it a promising tool for studying programmed cell death in cancer research.

Despite its promising applications, challenges remain in the large-scale synthesis and handling of (5-aminopent-1-yn-1-yl)trimethylsilane. Researchers have noted the need for optimized protocols to ensure reproducibility and safety, particularly given the compound's reactive alkyne moiety. Recent advancements in synthetic methodologies, such as flow chemistry, have shown potential in addressing these challenges, offering more efficient and scalable routes for its production.

In conclusion, (5-aminopent-1-yn-1-yl)trimethylsilane (CAS: 154188-73-5) represents a valuable tool in chemical biology and pharmaceutical research. Its versatility in bioconjugation, drug discovery, and probe development underscores its importance in advancing our understanding of biological systems and therapeutic interventions. Future research should focus on overcoming synthetic challenges and expanding its applications in emerging areas such as targeted drug delivery and personalized medicine.

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