Cas no 111600-89-6 (Thiazole, 4-ethynyl-)

Thiazole, 4-ethynyl- is a heterocyclic compound featuring a thiazole core with an ethynyl substituent at the 4-position. This structure imparts unique reactivity, making it a valuable intermediate in organic synthesis, particularly in the development of pharmaceuticals, agrochemicals, and functional materials. The ethynyl group enables efficient cross-coupling reactions, such as Sonogashira or click chemistry, facilitating the construction of complex molecular architectures. Its rigid thiazole backbone contributes to enhanced stability and electronic properties, useful in optoelectronic applications. The compound’s versatility and modularity make it a preferred choice for researchers seeking to tailor molecular properties for targeted applications. Proper handling under inert conditions is recommended due to its potential sensitivity.
Thiazole, 4-ethynyl- structure
Thiazole, 4-ethynyl- structure
Product Name:Thiazole, 4-ethynyl-
CAS No:111600-89-6
MF:C5H3NS
MW:109.149019479752
MDL:MFCD18207415
CID:129328
PubChem ID:22238491
Update Time:2025-09-28

Thiazole, 4-ethynyl- Chemical and Physical Properties

Names and Identifiers

    • Thiazole, 4-ethynyl-
    • 4-Ethynyl-1,3-thiazole
    • 4-ethynylthiazole
    • 4-ethynyl-Thiazole
    • ACMC-20mehz
    • AG-D-30123
    • CTK0H2854
    • KB-72430
    • MFCD18207415
    • DTXSID20623679
    • EN300-787622
    • 111600-89-6
    • SNNHMXYMKWHUBM-UHFFFAOYSA-N
    • SCHEMBL1725404
    • AKOS040822004
    • Thiazole, 4-ethynyl-
    • THIAZOLE,4-ETHYNYL-
    • G64801
    • MDL: MFCD18207415
    • Inchi: 1S/C5H3NS/c1-2-5-3-7-4-6-5/h1,3-4H
    • InChI Key: SNNHMXYMKWHUBM-UHFFFAOYSA-N
    • SMILES: S1C=NC(C#C)=C1

Computed Properties

  • Exact Mass: 108.99869
  • Monoisotopic Mass: 108.99862027g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 7
  • Rotatable Bond Count: 1
  • Complexity: 102
  • 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: 1.2
  • Topological Polar Surface Area: 41.1?2

Experimental Properties

  • Density: 1.21±0.1 g/cm3 (20 oC 760 Torr),
  • Boiling Point: 179.7±13.0 oC (760 Torr),
  • Flash Point: 67.0±8.7 oC,
  • Solubility: Slightly soluble (1.3 g/l) (25 o C),
  • PSA: 12.89
  • LogP: 1.12440

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Additional information on Thiazole, 4-ethynyl-

Thiazole, 4-Ethynyl: A Comprehensive Overview

Thiazole, 4-Ethynyl, also known by its CAS number 111600-89-6, is a heterocyclic compound that has garnered significant attention in the fields of organic chemistry and materials science. This compound belongs to the thiazole family, which is a five-membered ring containing sulfur and nitrogen atoms. The presence of an ethynyl group at the fourth position of the thiazole ring imparts unique electronic and structural properties to this compound, making it a valuable molecule for various applications.

Recent studies have highlighted the potential of Thiazole, 4-Ethynyl in drug discovery and development. Its ability to act as a bioisostere for other functional groups has made it a promising candidate in the design of novel therapeutic agents. For instance, researchers have explored its role in mimicking the pharmacophoric elements of existing drugs, thereby enhancing bioavailability and reducing toxicity. This has led to its incorporation into several lead compounds targeting various disease states, including cancer and neurodegenerative disorders.

In addition to its medicinal applications, Thiazole, 4-Ethynyl has found utility in materials science. The compound's ability to form stable coordination complexes with metal ions has been leveraged in the synthesis of metal-organic frameworks (MOFs) and other advanced materials. These materials exhibit exceptional porosity and stability, making them ideal for gas storage, catalysis, and sensing applications. Recent advancements in MOF synthesis have further underscored the importance of Thiazole, 4-Ethynyl as a key building block.

The synthesis of Thiazole, 4-Ethynyl has also been a topic of extensive research. Traditional methods involving multi-step reactions have been gradually replaced by more efficient protocols that utilize transition metal catalysis. For example, the use of palladium-catalyzed cross-coupling reactions has enabled the straightforward construction of the thiazole ring with high regioselectivity. These advancements have not only improved the yield but also reduced the environmental footprint of the synthesis process.

The electronic properties of Thiazole, 4-Ethynyl make it an attractive candidate for optoelectronic applications. Its conjugated system allows for efficient charge transport and absorption in the visible region, which is advantageous for applications such as organic light-emitting diodes (OLEDs) and photovoltaic devices. Recent studies have demonstrated its potential as an electron transport layer in OLEDs, where it exhibits excellent charge mobility and stability under operational conditions.

Beyond its technical applications, Thiazole, 4-Ethynyl has also been studied for its biological activity. In vitro assays have shown that this compound exhibits moderate antibacterial and antifungal properties, suggesting its potential use as a natural product-inspired antimicrobial agent. Furthermore, its ability to modulate cellular signaling pathways has opened avenues for its exploration in anti-inflammatory and anticancer therapies.

In conclusion, Thiazole, 4-Ethynyl, with its unique chemical structure and versatile properties, continues to be a focal point in contemporary research across multiple disciplines. Its applications span drug discovery, materials science, optoelectronics, and biotechnology, underscoring its significance as a multifaceted chemical entity. As research progresses, it is anticipated that new insights into its properties will further expand its utility in both academic and industrial settings.

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