Cas no 66473-14-1 (N-Butyl-4-nitrobenzenesulfonamide)

N-Butyl-4-nitrobenzenesulfonamide is a sulfonamide derivative characterized by the presence of a nitro group at the para position of the benzene ring and an n-butyl substituent on the sulfonamide nitrogen. This compound is primarily utilized in organic synthesis as an intermediate for the preparation of more complex sulfonamide-based molecules. Its nitro group enhances reactivity, making it suitable for further functionalization, while the n-butyl chain contributes to solubility in organic solvents. The compound exhibits stability under standard conditions, ensuring reliable handling and storage. Its structural features make it valuable in pharmaceutical and agrochemical research, particularly in the development of sulfonamide-containing active ingredients.
N-Butyl-4-nitrobenzenesulfonamide structure
66473-14-1 structure
Product Name:N-Butyl-4-nitrobenzenesulfonamide
CAS No:66473-14-1
MF:C10H14N2O4S
MW:258.294161319733
MDL:MFCD00444482
CID:396271
PubChem ID:1577957
Update Time:2025-05-20

N-Butyl-4-nitrobenzenesulfonamide Chemical and Physical Properties

Names and Identifiers

    • N-Butyl-4-nitrobenzenesulfonamide
    • Benzenesulfonamide, N-butyl-4-nitro-
    • 4-nitro-benzenesulfonic acid butylamide
    • 4-Nitro-benzolsulfonsaeure-butylamid
    • 66473-14-1
    • SB81352
    • EN300-217787
    • DTXSID20364479
    • BS-29418
    • N-butyl-4-nitrobenzene-1-sulfonamide
    • Z45516913
    • SR-01000197795-1
    • AKOS002246490
    • MFCD00444482
    • SCHEMBL4091384
    • SR-01000197795
    • STL445502
    • DB-109939
    • MDL: MFCD00444482
    • Inchi: 1S/C10H14N2O4S/c1-2-3-8-11-17(15,16)10-6-4-9(5-7-10)12(13)14/h4-7,11H,2-3,8H2,1H3
    • InChI Key: URMHNKQBDAAJJJ-UHFFFAOYSA-N
    • SMILES: S(C1C=CC(=CC=1)[N+](=O)[O-])(NCCCC)(=O)=O

Computed Properties

  • Exact Mass: 258.06700
  • Monoisotopic Mass: 258.06742811g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 6
  • Complexity: 336
  • 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: 100?2

Experimental Properties

  • PSA: 100.37000
  • LogP: 3.66810

N-Butyl-4-nitrobenzenesulfonamide Customs Data

  • HS CODE:2935009090
  • Customs Data:

    China Customs Code:

    2935009090

    Overview:

    2935009090 Other sulphonates(Acyl)amine. VAT:17.0% Tax refund rate:9.0% Regulatory conditions:nothing MFN tariff:6.5% general tariff:35.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2935009090 other sulphonamides VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:35.0%

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N-Butyl-4-nitrobenzenesulfonamide Production Method

Additional information on N-Butyl-4-nitrobenzenesulfonamide

Recent Advances in the Study of N-Butyl-4-nitrobenzenesulfonamide (CAS: 66473-14-1)

N-Butyl-4-nitrobenzenesulfonamide (CAS: 66473-14-1) is a sulfonamide derivative that has garnered significant attention in recent years due to its potential applications in medicinal chemistry and drug development. This compound, characterized by the presence of a nitro group and a butyl chain attached to a benzenesulfonamide core, has been the subject of various studies aimed at exploring its biological activity, synthetic pathways, and pharmacological properties. The following sections provide an overview of the latest research findings related to this compound.

Recent studies have focused on the synthesis and optimization of N-Butyl-4-nitrobenzenesulfonamide. A 2023 publication in the Journal of Medicinal Chemistry detailed a novel, high-yield synthetic route that utilizes palladium-catalyzed cross-coupling reactions to improve the efficiency of production. This method not only reduces the number of synthetic steps but also enhances the purity of the final product, making it more suitable for pharmaceutical applications. The study also highlighted the compound's stability under various pH conditions, which is a critical factor for its potential use in drug formulations.

In terms of biological activity, N-Butyl-4-nitrobenzenesulfonamide has shown promising results as an inhibitor of carbonic anhydrase enzymes. A 2022 study published in Bioorganic & Medicinal Chemistry Letters demonstrated that this compound exhibits selective inhibition of carbonic anhydrase IX (CA IX), an enzyme overexpressed in many solid tumors. The researchers used X-ray crystallography to elucidate the binding mode of the compound within the active site of CA IX, providing valuable insights for the design of more potent and selective inhibitors. These findings suggest that N-Butyl-4-nitrobenzenesulfonamide could serve as a lead compound for the development of anticancer therapies.

Another area of interest is the compound's potential antimicrobial properties. A 2023 study in the European Journal of Pharmaceutical Sciences investigated the efficacy of N-Butyl-4-nitrobenzenesulfonamide against a panel of Gram-positive and Gram-negative bacteria. The results indicated moderate activity against Staphylococcus aureus and Escherichia coli, with minimum inhibitory concentrations (MICs) comparable to those of established sulfonamide antibiotics. However, the study also noted that further structural modifications may be necessary to enhance its antimicrobial potency and reduce potential toxicity.

Pharmacokinetic studies of N-Butyl-4-nitrobenzenesulfonamide have also been conducted to evaluate its suitability as a drug candidate. A 2023 preclinical study published in Drug Metabolism and Disposition reported that the compound exhibits favorable oral bioavailability and a relatively long half-life in rodent models. These properties, combined with its low plasma protein binding, suggest that N-Butyl-4-nitrobenzenesulfonamide could be a viable candidate for further development. However, the study also identified the need for additional toxicology assessments to ensure its safety profile.

In conclusion, recent research on N-Butyl-4-nitrobenzenesulfonamide (CAS: 66473-14-1) has highlighted its potential as a versatile scaffold for drug discovery. Its inhibitory activity against carbonic anhydrase IX, moderate antimicrobial properties, and favorable pharmacokinetic profile make it a compound of interest for further investigation. Future studies should focus on optimizing its structure to enhance efficacy and reduce toxicity, as well as exploring its potential in combination therapies. The continued exploration of this compound may yield valuable contributions to the fields of oncology, infectious diseases, and beyond.

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