Cas no 1261438-96-3 (2-fluoro-5-isocyanatobenzonitrile)

2-Fluoro-5-isocyanatobenzonitrile is a versatile aromatic isocyanate derivative featuring both a reactive isocyanate group and an electron-withdrawing nitrile substituent, enhanced by fluorine substitution at the ortho position. This compound is particularly valuable in organic synthesis and pharmaceutical intermediates due to its dual functionality, enabling selective reactions such as nucleophilic additions or cyclizations. The fluorine atom imparts increased stability and influences electronic properties, while the isocyanate group offers reactivity toward amines, alcohols, and other nucleophiles. Its structural features make it suitable for constructing heterocycles or functionalized aromatic scaffolds. The nitrile group further expands utility in cross-coupling or hydrolysis reactions. Proper handling is essential due to the isocyanate's moisture sensitivity.
2-fluoro-5-isocyanatobenzonitrile structure
1261438-96-3 structure
Product Name:2-fluoro-5-isocyanatobenzonitrile
CAS No:1261438-96-3
MF:C8H3FN2O
MW:162.1206
MDL:MFCD18269700
CID:4740747
PubChem ID:63109919
Update Time:2026-02-25

2-fluoro-5-isocyanatobenzonitrile Chemical and Physical Properties

Names and Identifiers

    • Benzonitrile, 2-fluoro-5-isocyanato-
    • 2-fluoro-5-isocyanatobenzonitrile
    • MDL: MFCD18269700
    • Inchi: 1S/C8H3FN2O/c9-8-2-1-7(11-5-12)3-6(8)4-10/h1-3H
    • InChI Key: GXUMDKKEXDQAIW-UHFFFAOYSA-N
    • SMILES: FC1C([H])=C([H])C(=C([H])C=1C#N)N=C=O

Computed Properties

  • Exact Mass: 162.022941g/mol
  • Monoisotopic Mass: 162.022941g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 251
  • 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
  • Topological Polar Surface Area: 53.2
  • Molecular Weight: 162.12g/mol
  • XLogP3: 2.5

2-fluoro-5-isocyanatobenzonitrile Pricemore >>

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Additional information on 2-fluoro-5-isocyanatobenzonitrile

2-Fluoro-5-Isocyanatobenzonitrile: A Comprehensive Overview

2-Fluoro-5-isocyanatobenzonitrile, also known by its CAS number 1261438-96-3, is a versatile and intriguing compound that has garnered significant attention in the fields of organic chemistry, materials science, and pharmaceutical research. This compound is characterized by its unique structure, which combines a fluorine atom, an isocyanate group, and a cyano group on a benzene ring. The presence of these functional groups makes it highly reactive and suitable for a wide range of applications.

The synthesis of 2-fluoro-5-isocyanatobenzonitrile typically involves multi-step processes that require precise control over reaction conditions. Recent advancements in synthetic methodologies have enabled the efficient production of this compound with high purity. Researchers have explored various routes, including nucleophilic aromatic substitution and coupling reactions, to optimize its synthesis. These efforts have not only improved the yield but also opened new avenues for its application in diverse chemical transformations.

One of the most notable features of 2-fluoro-5-isocyanatobenzonitrile is its reactivity. The isocyanate group (-NCO) is highly electrophilic and readily reacts with nucleophiles such as amines, alcohols, and thiols. This reactivity has been leveraged in the development of novel materials, including polyurethanes and coatings. Recent studies have demonstrated that incorporating this compound into polymer formulations can significantly enhance their mechanical properties and thermal stability.

In the pharmaceutical industry, 2-fluoro-5-isocyanatobenzonitrile has shown promise as an intermediate in drug discovery. Its ability to undergo various transformations makes it a valuable building block for constructing complex molecular architectures. For instance, researchers have utilized this compound to synthesize bioactive molecules with potential applications in cancer therapy and anti-inflammatory treatments. The fluorine atom in its structure contributes to its lipophilicity, which is often desirable in drug design.

The electronic properties of 2-fluoro-5-isocyanatobenzonitrile also make it an interesting candidate for use in electronic materials. The cyano group (-CN) introduces electron-withdrawing effects, which can modulate the electronic characteristics of the molecule. Recent investigations have explored its potential as a component in organic semiconductors and light-emitting diodes (LEDs). These studies highlight its role in enhancing device performance by improving charge transport properties.

In terms of environmental impact, the handling and disposal of 2-fluoro-5-isocyanatobenzonitrile require careful consideration due to its chemical reactivity. Researchers have developed eco-friendly protocols for its synthesis and application to minimize waste generation and reduce environmental footprint. These sustainable practices align with the growing demand for green chemistry in modern industrial processes.

The future prospects for 2-fluoro-5-isocyanatobenzonitrile are bright, with ongoing research focusing on expanding its applications across various domains. Its unique combination of functional groups continues to inspire innovative uses in material science, pharmaceuticals, and electronics. As scientific understanding of this compound deepens, it is likely to play an increasingly important role in advancing technological frontiers.

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