Cas no 2070-48-6 (4-trifluoromethanesulfonylbenzene-1-sulfonamide)

4-Trifluoromethanesulfonylbenzene-1-sulfonamide is a specialized sulfonamide derivative featuring both trifluoromethanesulfonyl and sulfonamide functional groups. This compound is of significant interest in synthetic organic chemistry due to its electron-withdrawing properties, which enhance reactivity in nucleophilic substitution and cross-coupling reactions. The trifluoromethanesulfonyl group contributes to high stability and resistance to hydrolysis, making it valuable in the development of pharmaceuticals, agrochemicals, and advanced materials. Its dual functionality allows for versatile applications as an intermediate in the synthesis of biologically active molecules or as a precursor for sulfonamide-based catalysts. The compound's well-defined structure and purity ensure consistent performance in demanding chemical processes.
4-trifluoromethanesulfonylbenzene-1-sulfonamide structure
2070-48-6 structure
Product Name:4-trifluoromethanesulfonylbenzene-1-sulfonamide
CAS No:2070-48-6
MF:C7H6F3NO4S2
MW:289.252049922943
MDL:MFCD00159249
CID:1395691
PubChem ID:23501091
Update Time:2025-05-28

4-trifluoromethanesulfonylbenzene-1-sulfonamide Chemical and Physical Properties

Names and Identifiers

    • Benzenesulfonamide, 4-[(trifluoromethyl)sulfonyl]-
    • 4-(trifluoromethylsulfonyl)benzenesulfonamide
    • 4-trifluoromethanesulfonylbenzene-1-sulfonamide
    • 2070-48-6
    • SCHEMBL6849852
    • 4-(Trifluoromethanesulfonyl)benzene-1-sulfonamide
    • AKOS010998386
    • EN300-273785
    • DTXSID00634546
    • UIMYKAIGUAXWCJ-UHFFFAOYSA-N
    • MDL: MFCD00159249
    • Inchi: 1S/C7H6F3NO4S2/c8-7(9,10)16(12,13)5-1-3-6(4-2-5)17(11,14)15/h1-4H,(H2,11,14,15)
    • InChI Key: UIMYKAIGUAXWCJ-UHFFFAOYSA-N
    • SMILES: S(C(F)(F)F)(C1C=CC(=CC=1)S(N)(=O)=O)(=O)=O

Computed Properties

  • Exact Mass: 288.96908
  • Monoisotopic Mass: 288.96903451g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 8
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 2
  • Complexity: 463
  • 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: 111?2

Experimental Properties

  • PSA: 94.3

4-trifluoromethanesulfonylbenzene-1-sulfonamide Pricemore >>

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Additional information on 4-trifluoromethanesulfonylbenzene-1-sulfonamide

Comprehensive Overview of 4-Trifluoromethanesulfonylbenzene-1-sulfonamide (CAS No. 2070-48-6): Properties, Applications, and Industry Insights

4-Trifluoromethanesulfonylbenzene-1-sulfonamide (CAS No. 2070-48-6), a specialized sulfonamide derivative, has garnered significant attention in pharmaceutical and agrochemical research due to its unique trifluoromethanesulfonyl functional group. This compound, often abbreviated as TFMSA, exemplifies the growing demand for fluorinated building blocks in modern synthetic chemistry. Its molecular structure combines a benzene sulfonamide core with a trifluoromethylsulfonyl substituent, enabling exceptional electron-withdrawing properties and metabolic stability – key traits driving its adoption in drug discovery pipelines.

The rise of precision medicine and targeted therapies has amplified interest in 4-trifluoromethanesulfonylbenzene-1-sulfonamide as researchers explore its potential in modulating enzyme inhibition and protein-protein interactions. Recent studies highlight its utility in developing kinase inhibitors, particularly for oncology applications where the CF3 group enhances binding affinity to ATP pockets. The compound's lipophilicity parameters (LogP ~1.8) and hydrogen bonding capacity make it a versatile intermediate for optimizing bioavailability in candidate molecules.

From a synthetic chemistry perspective, CAS 2070-48-6 serves as a valuable precursor for cross-coupling reactions, particularly in palladium-catalyzed transformations. Its sulfonamide moiety participates readily in N-alkylation and N-arylation processes, while the triflyl group acts as an excellent leaving group in nucleophilic aromatic substitution (SNAr) reactions. These characteristics have positioned it as a multifunctional synthon in constructing complex heterocycles for material science applications.

Environmental considerations surrounding fluorinated compounds have spurred innovation in the handling and recycling of 4-trifluoromethanesulfonylbenzene-1-sulfonamide. Advanced green chemistry protocols now employ catalytic methods to minimize waste generation during its utilization. The compound's hydrolytic stability (pH 2-11) and thermal resilience (decomposition >200°C) contribute to safer processing compared to traditional sulfonyl chlorides, addressing industry concerns about process safety and sustainability metrics.

Analytical characterization of TFMSA typically involves HPLC-UV (retention time ~6.2 min in C18 methods) and LC-MS (m/z 274 [M+H]+). The distinctive 19F NMR signal at -78 ppm serves as a diagnostic marker for quality control. These analytical fingerprints have become crucial for suppliers ensuring batch-to-batch consistency, particularly for GMP applications where impurity profiles must meet stringent ICH guidelines.

Market trends indicate growing adoption of 2070-48-6 in electronic materials, where its sulfonamide group facilitates the development of polymeric electrolytes for battery technologies. The compound's ability to modify surface energy and enhance charge transport properties has sparked interest in organic semiconductors and photovoltaic materials. This diversification beyond life sciences underscores the compound's multidisciplinary utility in addressing contemporary technological challenges.

Regulatory aspects of 4-trifluoromethanesulfonylbenzene-1-sulfonamide manufacturing emphasize proper industrial hygiene practices due to its fine particulate nature. While not classified as hazardous under GHS, standard PPE protocols (nitrile gloves, dust masks) are recommended during handling. The compound's REACH registration status and global inventory listings (TSCA, EINECS) ensure compliance for international trade, with typical shipping classifications as non-dangerous goods.

Future research directions for CAS 2070-48-6 focus on expanding its role in bioconjugation chemistry and proteolysis targeting chimeras (PROTACs). The compound's balanced solubility profile (soluble in DMSO, acetonitrile) and compatibility with click chemistry platforms position it as an attractive component for next-generation therapeutics. As the pharmaceutical industry prioritizes fragment-based drug design, this sulfonamide derivative continues to demonstrate value in constructing privileged scaffolds with tailored physicochemical properties.

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