Cas no 5038-59-5 (4-(2-Bromoacetyl)benzenesulfonyl Chloride)

4-(2-Bromoacetyl)benzenesulfonyl chloride is a versatile sulfonylating and bromoacetylating reagent used in organic synthesis and pharmaceutical research. Its reactive benzenesulfonyl chloride and bromoacetyl groups enable selective modifications of amines, alcohols, and other nucleophiles, facilitating the preparation of sulfonamides, sulfonate esters, and other functionalized intermediates. The compound’s dual functionality allows for efficient crosslinking or derivatization in peptide chemistry and small-molecule drug development. It is particularly valuable in constructing bioactive molecules due to its high reactivity and stability under controlled conditions. Suitable for use in anhydrous environments, it requires careful handling to prevent hydrolysis. The product is typically supplied as a crystalline solid with consistent purity for reliable synthetic applications.
4-(2-Bromoacetyl)benzenesulfonyl Chloride structure
5038-59-5 structure
Product Name:4-(2-Bromoacetyl)benzenesulfonyl Chloride
CAS No:5038-59-5
MF:C8H6BrClO3S
MW:297.553439617157
MDL:MFCD03424999
CID:821223
PubChem ID:2756834
Update Time:2025-06-08

4-(2-Bromoacetyl)benzenesulfonyl Chloride Chemical and Physical Properties

Names and Identifiers

    • 4-(2-Bromoacetyl)benzene-1-sulfonyl chloride
    • 4-(2-BROMOACETYL)BENZENESULFONYL CHLORIDE
    • 2-bromo-4'-chlorosulfonylacetophenone
    • 4-(2-bromanylethanoyl)benzenesulfonyl chloride
    • 4-(2-bromoacetyl)benzenesulfonic acid chloride
    • 4-(2-bromo-acetyl)-benzenesulfonyl chloride
    • YSZVEXHEBFFCSK-UHFFFAOYSA-N
    • MFCD03424999
    • AKOS016846016
    • CS-0171005
    • AS-36537
    • SCHEMBL3144401
    • 4-(2-Bromoacetyl)benzene-1-sulfonylchloride
    • DTXSID70373576
    • 4-(2-Bromoacetyl)benzenesulfonylchloride
    • 5038-59-5
    • 4-(2-Bromoacetyl)benzenesulfonyl Chloride
    • MDL: MFCD03424999
    • Inchi: 1S/C8H6BrClO3S/c9-5-8(11)6-1-3-7(4-2-6)14(10,12)13/h1-4H,5H2
    • InChI Key: YSZVEXHEBFFCSK-UHFFFAOYSA-N
    • SMILES: BrCC(C1C=CC(=CC=1)S(=O)(=O)Cl)=O

Computed Properties

  • Exact Mass: 295.89100
  • Monoisotopic Mass: 295.89096g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 3
  • Complexity: 301
  • 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: 2.4
  • Topological Polar Surface Area: 59.6?2

Experimental Properties

  • Color/Form: White to Yellow Solid
  • PSA: 59.59000
  • LogP: 3.27250

4-(2-Bromoacetyl)benzenesulfonyl Chloride Security Information

4-(2-Bromoacetyl)benzenesulfonyl Chloride Customs Data

  • HS CODE:2914700090
  • Customs Data:

    China Customs Code:

    2914700090

    Overview:

    2914700090 Halogenation of other ketones and quinones\Sulfonated derivative(Including nitrated and nitrosative derivatives). VAT:17.0% Tax refund rate:9.0% Regulatory conditions:nothing MFN tariff:5.5% general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to, Acetone declared packaging

    Summary:

    HS: 2914700090 halogenated, sulphonated, nitrated or nitrosated derivatives of ketones and quinones, whether or not with other oxygen function Tax rebate rate:9.0% Supervision conditions:none VAT:17.0% MFN tariff:5.5% General tariff:30.0%

4-(2-Bromoacetyl)benzenesulfonyl Chloride Pricemore >>

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Additional information on 4-(2-Bromoacetyl)benzenesulfonyl Chloride

Recent Advances in the Application of 4-(2-Bromoacetyl)benzenesulfonyl Chloride (CAS 5038-59-5) in Chemical Biology and Pharmaceutical Research

4-(2-Bromoacetyl)benzenesulfonyl Chloride (CAS 5038-59-5) is a versatile chemical reagent that has garnered significant attention in recent years due to its unique reactivity and potential applications in chemical biology and pharmaceutical research. This compound serves as a key intermediate in the synthesis of various biologically active molecules, particularly in the development of enzyme inhibitors, covalent probes, and targeted therapeutics. The presence of both a reactive bromoacetyl group and a sulfonyl chloride moiety enables this molecule to participate in diverse chemical transformations, making it a valuable tool for researchers in drug discovery and chemical biology.

Recent studies have highlighted the utility of 4-(2-Bromoacetyl)benzenesulfonyl Chloride in the development of covalent inhibitors targeting essential enzymes in disease pathways. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its effectiveness in creating irreversible inhibitors of cysteine proteases, which play crucial roles in various pathological conditions including cancer metastasis and inflammatory diseases. The researchers utilized the compound's ability to form stable covalent bonds with nucleophilic amino acid residues, achieving high selectivity and potency in their inhibitor designs.

In the field of chemical proteomics, 4-(2-Bromoacetyl)benzenesulfonyl Chloride has emerged as a valuable tool for activity-based protein profiling (ABPP). A recent Nature Chemical Biology publication (2024) described its use in developing novel probes for mapping enzyme activities in complex biological systems. The bromoacetyl group's reactivity towards catalytic nucleophiles, combined with the sulfonyl chloride's ability to introduce reporter tags, makes this compound particularly useful for creating multifunctional probes that can simultaneously capture and identify enzyme activities.

Pharmaceutical applications of this compound have expanded significantly, with several research groups reporting its incorporation into drug candidates targeting protein-protein interactions. A 2023 study in ACS Chemical Biology demonstrated how derivatives of 4-(2-Bromoacetyl)benzenesulfonyl Chloride could be used to develop small molecules that disrupt critical protein-protein interfaces in oncogenic signaling pathways. The compound's ability to introduce both covalent anchoring points and structural diversity has proven particularly valuable in this challenging area of drug discovery.

Recent synthetic methodology developments have further enhanced the utility of 4-(2-Bromoacetyl)benzenesulfonyl Chloride. A 2024 publication in Organic Letters described a novel one-pot procedure for its conversion into various heterocyclic scaffolds, significantly expanding the structural diversity accessible from this key intermediate. These advances have important implications for medicinal chemistry, where rapid access to diverse molecular architectures is often crucial for optimizing drug candidates.

Safety and handling considerations for 4-(2-Bromoacetyl)benzenesulfonyl Chloride remain an important research focus. Recent improvements in synthetic protocols have reduced the need for hazardous reagents in its production, while new stabilization methods have extended its shelf life for laboratory use. These developments, reported in a 2023 Chemical Research in Toxicology article, have made the compound more accessible to researchers while maintaining high standards of laboratory safety.

Looking forward, the unique chemical properties of 4-(2-Bromoacetyl)benzenesulfonyl Chloride (CAS 5038-59-5) position it as a key building block for emerging therapeutic modalities. Current research directions include its application in targeted protein degradation strategies and the development of covalent drugs with improved selectivity profiles. As these applications mature, this versatile compound is likely to play an increasingly important role in bridging chemical biology and pharmaceutical development.

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