Cas no 18800-01-6 (2-Iodothiophene-3-carbonitrile)

2-Iodothiophene-3-carbonitrile structure
18800-01-6 structure
Product Name:2-Iodothiophene-3-carbonitrile
CAS No:18800-01-6
MF:C5H2INS
MW:235.045551776886
CID:1090631
PubChem ID:10977399
Update Time:2025-04-23

2-Iodothiophene-3-carbonitrile Chemical and Physical Properties

Names and Identifiers

    • 2-Iodothiophene-3-carbonitrile
    • DTXSID40450520
    • SCHEMBL3139164
    • 2-iodo-thiophene-3-carbonitrile
    • SAARTNKVCGHQCW-UHFFFAOYSA-N
    • MFCD09056773
    • 2-iodo-3-cyano-thiophene
    • 18800-01-6
    • 3-Thiophenecarbonitrile, 2-iodo-
    • Inchi: 1S/C5H2INS/c6-5-4(3-7)1-2-8-5/h1-2H
    • InChI Key: SAARTNKVCGHQCW-UHFFFAOYSA-N
    • SMILES: IC1=C(C#N)C=CS1

Computed Properties

  • Exact Mass: 234.89486
  • Monoisotopic Mass: 234.89527g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 8
  • Rotatable Bond Count: 0
  • Complexity: 128
  • 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: 2
  • Topological Polar Surface Area: 52?2

Experimental Properties

  • PSA: 23.79

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2-Iodothiophene-3-carbonitrile Related Literature

Additional information on 2-Iodothiophene-3-carbonitrile

2-Iodothiophene-3-Carbonitrile: A Comprehensive Overview

2-Iodothiophene-3-carbonitrile (CAS No. 18800-01-6) is a versatile organic compound with significant applications in various fields of chemistry. This compound, also referred to as iodothiophene nitrile, belongs to the class of heterocyclic compounds, specifically thiophenes, which are five-membered aromatic rings containing one sulfur atom. The presence of an iodine atom at the 2-position and a cyano group at the 3-position makes this compound unique and highly functional.

The synthesis of 2-iodothiophene-3-carbonitrile has been extensively studied, with researchers exploring various methodologies to optimize its production. Recent advancements in catalytic processes have enabled the synthesis of this compound with higher yields and improved purity. For instance, studies have demonstrated the use of transition metal catalysts, such as palladium complexes, to facilitate coupling reactions that lead to the formation of this compound. These methods not only enhance the efficiency of synthesis but also contribute to the sustainability of chemical processes by reducing waste and energy consumption.

One of the most notable applications of 2-iodothiophene-3-carbonitrile is in materials science, particularly in the development of advanced materials for electronic devices. The compound's electronic properties make it an ideal candidate for use in organic semiconductors and light-emitting diodes (LEDs). Recent research has highlighted its potential as a building block for constructing novel π-conjugated systems, which are essential for achieving high electron mobility in organic electronics. For example, studies have shown that incorporating 2-iodothiophene-3-carbonitrile into polymer frameworks can significantly enhance the electrical conductivity and stability of resulting materials.

In addition to its role in materials science, 2-iodothiophene-3-carbonitrile has also found applications in medicinal chemistry. The compound's ability to act as a bioisostere—a structural analog that retains similar biological activity while altering physical properties—has made it valuable in drug design. Researchers have explored its potential as a scaffold for developing new pharmaceutical agents targeting various diseases, including cancer and neurodegenerative disorders. Recent findings suggest that derivatives of this compound exhibit promising anti-proliferative activity against cancer cell lines, making it a subject of interest for further preclinical studies.

The reactivity of 2-iodothiophene-3-carbonitrile is another area that has garnered significant attention from chemists. The iodine atom at the 2-position serves as an excellent leaving group, enabling nucleophilic substitution reactions under mild conditions. This property has been exploited in the development of novel synthetic routes for constructing complex molecules. For instance, recent studies have utilized this compound as a precursor for synthesizing heterocyclic compounds with diverse functionalities, such as pyridines and quinolines. These compounds hold potential applications in catalysis, sensors, and energy storage systems.

Furthermore, the study of 2-iodothiophene-3-carbonitrile has contributed to our understanding of thiophene chemistry and its role in aromaticity. The compound's structure provides insights into how substituents influence the electronic properties and reactivity of thiophenes. Recent computational studies have employed density functional theory (DFT) to analyze the electronic structure of this compound, revealing its unique π-system and charge distribution patterns. These findings have implications for designing new thiophene derivatives with tailored properties for specific applications.

In conclusion, 2-iodothiophene-3-carbonitrile (CAS No. 18800-01-6) is a multifaceted compound with significant contributions to various areas of chemistry. Its versatility lies in its ability to serve as both a functional material and a valuable intermediate in organic synthesis. As research continues to uncover new applications and optimize its synthesis methods, this compound is poised to play an increasingly important role in advancing modern chemistry and technology.

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