Cas no 1773-42-8 (4-isocyanatobenzene-1-sulfonamide)

4-Isocyanatobenzene-1-sulfonamide is a reactive aromatic compound featuring both an isocyanate (–NCO) and a sulfonamide (–SO?NH?) functional group. This dual functionality enables its use as a versatile intermediate in organic synthesis, particularly for the preparation of sulfonamide-based polymers, pharmaceuticals, and agrochemicals. The isocyanate group allows for facile conjugation with nucleophiles such as amines or alcohols, while the sulfonamide moiety contributes to enhanced stability and potential bioactivity. Its well-defined reactivity profile makes it suitable for controlled derivatization in specialty chemical applications. The compound is typically handled under anhydrous conditions due to the moisture sensitivity of the isocyanate group.
4-isocyanatobenzene-1-sulfonamide structure
1773-42-8 structure
Product Name:4-isocyanatobenzene-1-sulfonamide
CAS No:1773-42-8
MF:C7H6N2O3S
MW:198.199140071869
CID:118066
PubChem ID:21494023
Update Time:2025-08-03

4-isocyanatobenzene-1-sulfonamide Chemical and Physical Properties

Names and Identifiers

    • Benzenesulfonamide,4-isocyanato-
    • 4-isocyanatobenzenesulfonamide
    • Benzenesulfonamide, 4-isocyanato- (9CI)
    • 4-isocyanatobenzene-1-sulfonamide
    • EN300-144238
    • 1773-42-8
    • Benzenesulfonamide, 4-isocyanato-
    • DTXSID60614869
    • IYSAYSBNKDUNKZ-UHFFFAOYSA-N
    • SCHEMBL242025
    • 4-Isocyanato-benzenesulfonamide
    • Inchi: 1S/C7H6N2O3S/c8-13(11,12)7-3-1-6(2-4-7)9-5-10/h1-4H,(H2,8,11,12)
    • InChI Key: IYSAYSBNKDUNKZ-UHFFFAOYSA-N
    • SMILES: S(C1C=CC(=CC=1)N=C=O)(N)(=O)=O

Computed Properties

  • Exact Mass: 198.00998
  • Monoisotopic Mass: 198.00991323g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 305
  • 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: 1.5
  • Topological Polar Surface Area: 98?2

Experimental Properties

  • PSA: 89.59

4-isocyanatobenzene-1-sulfonamide Pricemore >>

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4-isocyanatobenzene-1-sulfonamide Related Literature

Additional information on 4-isocyanatobenzene-1-sulfonamide

Recent Advances in the Application of 4-Isocyanatobenzene-1-sulfonamide (CAS: 1773-42-8) in Chemical Biology and Pharmaceutical Research

4-Isocyanatobenzene-1-sulfonamide (CAS: 1773-42-8) is a versatile chemical compound that has garnered significant attention in recent years due to its potential applications in chemical biology and pharmaceutical research. This sulfonamide derivative, characterized by its reactive isocyanate group, has been employed as a key intermediate in the synthesis of various biologically active molecules. Recent studies have explored its utility in drug discovery, particularly in the development of enzyme inhibitors and targeted therapeutics. The compound's unique chemical properties, including its ability to form stable covalent bonds with nucleophilic residues in proteins, make it a valuable tool for probing biological systems and designing novel pharmacophores.

One of the most notable advancements in the application of 4-isocyanatobenzene-1-sulfonamide is its role in the development of carbonic anhydrase inhibitors. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that derivatives of this compound exhibit potent inhibitory activity against several carbonic anhydrase isoforms, which are implicated in various pathological conditions, including glaucoma, epilepsy, and cancer. The researchers utilized structure-activity relationship (SAR) studies to optimize the compound's binding affinity and selectivity, leading to the identification of promising drug candidates with improved pharmacokinetic properties.

In addition to its therapeutic potential, 4-isocyanatobenzene-1-sulfonamide has also been employed as a chemical probe in proteomics research. A recent study in Nature Chemical Biology highlighted its use in activity-based protein profiling (ABPP), where it was shown to selectively label and identify active sites of sulfonamide-binding enzymes in complex biological samples. This approach provides valuable insights into enzyme function and facilitates the discovery of new drug targets. The study further demonstrated the compound's utility in mapping the interactome of sulfonamide-binding proteins, offering a powerful tool for understanding cellular signaling pathways.

The synthetic versatility of 4-isocyanatobenzene-1-sulfonamide has also been explored in materials science. A 2022 publication in ACS Applied Materials & Interfaces reported its use as a cross-linking agent in the fabrication of functional polymers with tunable properties. The researchers demonstrated that the compound's isocyanate group could react with hydroxyl or amine functionalities to form polyurethane or polyurea networks, respectively. These materials exhibited enhanced mechanical strength and chemical stability, making them suitable for applications in drug delivery systems and biomedical devices.

Despite these promising developments, challenges remain in the widespread adoption of 4-isocyanatobenzene-1-sulfonamide in pharmaceutical applications. Issues such as its reactivity profile, potential toxicity, and metabolic stability need to be carefully addressed in future studies. However, ongoing research efforts, including computational modeling and high-throughput screening, are expected to further elucidate its potential and expand its applications in chemical biology and drug discovery. As the field continues to evolve, 4-isocyanatobenzene-1-sulfonamide is poised to play an increasingly important role in the development of next-generation therapeutics and chemical tools.

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