• 1. Evolving better nanoparticles: Genetic algorithms for optimising cluster geometries
  Dalton Trans., 2003, 4193-4207
• 2. Estimating and correcting interference fringes in infrared spectra in infrared hyperspectral imaging
  Ghazal Azarfar,Ebrahim Aboualizadeh,Nicholas M. Walter,Simona Ratti,Camilla Olivieri,Alessandra Norici,Michael Nasse,Achim Kohler,Mario Giordano Analyst, 2018,143, 4674-4683
• 3. Distinguishing between polymorphic forms of linezolid by solid-phase electronic and vibrational circular dichroism?
  Jadwiga Frelek,Marcin Górecki,Marta ?aszcz,Agata Suszczyńska,Elemér Vass,Wojciech J. Szczepek Chem. Commun., 2012,48, 5295-5297
• 4. Examination of the hydrogen-bonding networks in small water clusters (n = 2–5, 13, 17) using absolutely localized molecular orbital energy decomposition analysis?
  Erika A. Cobar,Paul R. Horn,Robert G. Bergman,Martin Head-Gordon Phys. Chem. Chem. Phys., 2012,14, 15328-15339
• 5. Excimer emission and magnetoluminescence of radical-based zinc(ii) complexes doped in host crystals?
  Shojiro Kimura,Tetsuro Kusamoto Chem. Commun., 2020,56, 11195-11198

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Aniline and substituted anilines

Introduction to 4-Chloro-2-((trimethylsilyl)ethynyl)aniline (CAS No. 180624-15-1)

4-Chloro-2-((trimethylsilyl)ethynyl)aniline, identified by its Chemical Abstracts Service Number (CAS No.) 180624-15-1, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical chemistry and materials science. This compound belongs to the class of arylacetylenes and features a unique structural motif that combines a chloro-substituted benzene ring with an ethynyl group terminated by a trimethylsilyl (TMS) moiety. The presence of these functional groups makes it a versatile intermediate in synthetic chemistry, particularly in the development of novel therapeutic agents and advanced materials.

The< strong>4-Chloro-2-((trimethylsilyl)ethynyl)aniline molecule exhibits a high degree of reactivity due to the electron-withdrawing nature of the chloro group and the electron-donating effect of the trimethylsilyl group. This balance of electronic properties allows it to participate in a wide range of chemical transformations, including cross-coupling reactions, which are fundamental in modern drug synthesis. The silyl group, in particular, enhances the stability of the acetylene functionality, making it more amenable to handling and reaction conditions that would otherwise degrade sensitive alkyne compounds.

In recent years, there has been growing interest in the applications of< strong>4-Chloro-2-((trimethylsilyl)ethynyl)aniline in medicinal chemistry. Its structural features make it an excellent precursor for the synthesis of biologically active molecules. For instance, the chloro-substituted benzene ring can be readily modified through nucleophilic aromatic substitution or metal-catalyzed cross-coupling reactions to introduce various pharmacophores. The ethynyl group serves as a versatile handle for further functionalization, enabling the construction of complex molecular architectures.

One of the most compelling aspects of< strong>4-Chloro-2-((trimethylsilyl)ethynyl)aniline is its utility in the development of photopharmacophores—molecules designed to interact with light for therapeutic purposes. The acetylene functionality is particularly sensitive to light irradiation, allowing for controlled activation and deactivation of biological activity. This property has been exploited in the design of photoactivatable drugs that can be triggered by external stimuli, such as UV light, to induce a therapeutic response. Such systems have shown promise in treating various conditions, including cancer and inflammatory diseases.

The< strong>4-Chloro-2-((trimethylsilyl)ethynyl)aniline molecule also finds applications in materials science, particularly in the synthesis of organic semiconductors and conductive polymers. The conjugated system formed by the aromatic ring and the alkyne moiety contributes to its electronic properties, making it suitable for use in optoelectronic devices such as organic light-emitting diodes (OLEDs) and photovoltaic cells. Additionally, its ability to undergo controlled polymerization allows for the creation of novel materials with tailored mechanical and electrical properties.

In academic research,< strong>4-Chloro-2-((trimethylsilyl)ethynyl)aniline has been employed as a key intermediate in the synthesis of complex natural products and heterocyclic compounds. Its structural versatility enables chemists to access a wide range of molecular scaffolds that would be difficult or impossible to obtain through other means. For example, researchers have utilized this compound to construct novel analogs of bioactive molecules derived from plants and microorganisms, with potential therapeutic applications.

The synthesis of< strong>4-Chloro-2-((trimethylsilyl)ethynyl)aniline typically involves multi-step organic transformations that highlight its reactivity and synthetic utility. A common approach involves the palladium-catalyzed coupling of 2-chloroaniline with a terminal alkyne bearing a trimethylsilyl protecting group. This reaction proceeds efficiently under mild conditions and yields high yields of the desired product. The use of transition metal catalysts underscores the importance of these methodologies in modern synthetic chemistry.

The< strong>CAS No. 180624-15-1 designation ensures that researchers can reliably identify and procure this compound for their studies. Its unique molecular structure and reactivity make it a valuable tool in both academic research and industrial applications. As our understanding of its properties continues to grow, so too will its role in advancing pharmaceutical sciences and materials engineering.

In conclusion, 4-Chloro-2-((trimethylsilyl)ethynyl)aniline is a multifaceted compound with broad applications across multiple disciplines. Its structural features enable it to participate in diverse chemical transformations, making it an indispensable intermediate in drug discovery and material design. With ongoing research exploring new synthetic pathways and applications, this molecule is poised to remain at the forefront of chemical innovation for years to come.

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