Cas no 53297-69-1 (4-Amino-3-Bromobenzenesulphonamide)

4-Amino-3-Bromobenzenesulphonamide is a brominated aromatic sulphonamide compound with the molecular formula C?H?BrN?O?S. This intermediate is notable for its reactive amino and sulphonamide functional groups, making it valuable in organic synthesis and pharmaceutical applications. The bromine substituent enhances its utility in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, enabling the formation of complex aromatic structures. Its sulphonamide moiety also offers potential for derivatization in medicinal chemistry, particularly in the development of sulfa-drug analogs. The compound’s well-defined structure and purity ensure consistent performance in research and industrial processes. Proper handling is advised due to its potential reactivity.
4-Amino-3-Bromobenzenesulphonamide structure
53297-69-1 structure
Product Name:4-Amino-3-Bromobenzenesulphonamide
CAS No:53297-69-1
MF:C6H7BrN2O2S
MW:251.100979089737
MDL:MFCD03546509
CID:357614
PubChem ID:3526523
Update Time:2025-06-08

4-Amino-3-Bromobenzenesulphonamide Chemical and Physical Properties

Names and Identifiers

    • Benzenesulfonamide, 4-amino-3-bromo-
    • 4-amino-3-bromoBenzenesulfonamide
    • 2-Bromo-4-sulphamoylaniline
    • 3-Brom-4-amino-benzolsulfonamid-(1)
    • 3-bromo-4-amino-benzenesulfonamide
    • 3-Bromosulfanilamide
    • 4-Amino-3-brom-benzolsulfonsaeure-amid
    • 4-amino-3-bromo-benzenesulfonamide
    • 4-amino-3-bromo-benzenesulfonic acid amide
    • aromatic
    • heteroaromatic sulfonamide 9
    • CHEMBL6724
    • AKOS000263221
    • FT-0711646
    • AT14671
    • BDBM10864
    • SCHEMBL878968
    • 4-amino-3-bromobenzene-1-sulfonamide
    • GS1060
    • EN300-30640
    • PD182044
    • KQEVQYJWCZRLTJ-UHFFFAOYSA-N
    • Z315898994
    • DTXSID40393322
    • 53297-69-1
    • halogenosulfanilamide deriv. 5d
    • aromatic/heteroaromatic sulfonamide 9
    • DA-21402
    • 4-Amino-3-Bromobenzenesulphonamide
    • MDL: MFCD03546509
    • Inchi: 1S/C6H7BrN2O2S/c7-5-3-4(12(9,10)11)1-2-6(5)8/h1-3H,8H2,(H2,9,10,11)
    • InChI Key: KQEVQYJWCZRLTJ-UHFFFAOYSA-N
    • SMILES: BrC1=C(C=CC(=C1)S(N)(=O)=O)N

Computed Properties

  • Exact Mass: 249.94100
  • Monoisotopic Mass: 249.94116g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 249
  • 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: 0.5
  • Topological Polar Surface Area: 94.6?2

Experimental Properties

  • PSA: 94.56000
  • LogP: 3.04100

4-Amino-3-Bromobenzenesulphonamide Pricemore >>

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Additional information on 4-Amino-3-Bromobenzenesulphonamide

Comprehensive Overview of 4-Amino-3-Bromobenzenesulphonamide (CAS No. 53297-69-1)

4-Amino-3-Bromobenzenesulphonamide (CAS No. 53297-69-1) is a specialized aromatic sulfonamide derivative with significant applications in pharmaceutical and chemical research. This compound, characterized by its bromine and amino functional groups, serves as a versatile intermediate in organic synthesis. Its molecular structure, C6H7BrN2O2S, offers unique reactivity, making it valuable for designing novel bioactive molecules. Researchers frequently explore its potential in drug discovery, particularly for targeting enzymes like carbonic anhydrase, a hot topic in modern medicinal chemistry.

The growing interest in sulfonamide-based compounds stems from their broad-spectrum biological activities, including antimicrobial and anti-inflammatory properties. 4-Amino-3-Bromobenzenesulphonamide is often discussed in academic forums and patent literature as a precursor for heterocyclic synthesis, aligning with the trend of green chemistry and atom-efficient reactions. Its brominated aromatic core enables selective cross-coupling reactions, such as Suzuki-Miyaura couplings, which are pivotal in creating complex molecular architectures for agrochemicals and materials science.

From an analytical perspective, CAS No. 53297-69-1 is frequently referenced in chromatography and mass spectrometry studies due to its distinct UV-Vis absorption profile. Laboratories optimizing HPLC methods for sulfonamides often use this compound as a benchmark. Recent publications highlight its role in developing fluorescence probes, addressing the demand for sensitive detection tools in environmental monitoring—a high-search-volume topic linked to water quality assessments.

Industrial applications of 4-Amino-3-Bromobenzenesulphonamide include its use in dye synthesis, where its electron-withdrawing sulfonamide group enhances color fastness. This aligns with the surge in eco-friendly textile research, a niche frequently searched in conjunction with sustainable dyes. Additionally, its stability under acidic conditions makes it a candidate for corrosion inhibitors, another trending subject in material science forums.

Regulatory and safety profiles of 53297-69-1 are well-documented in compliance with REACH and FDA guidelines. While not classified as hazardous, proper handling protocols are emphasized in SDS sheets, reflecting the industry’s focus on lab safety best practices—a recurring query in educational and professional search engines. The compound’s low ecotoxicity further supports its adoption in green synthesis protocols, a priority for pharmaceutical manufacturers aiming to reduce environmental footprints.

In summary, 4-Amino-3-Bromobenzenesulphonamide exemplifies the intersection of traditional chemistry and cutting-edge research. Its multifaceted utility—from drug scaffolds to analytical standards—positions it as a high-value intermediate in both academic and industrial settings. As interest grows in tailored sulfonamides and halogenated aromatics, this compound remains a focal point for innovation, answering pressing questions in structure-activity relationships and process optimization.

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