Cas no 125607-05-8 (2-chloro-4-fluoro-5-nitrobenzene-1-sulfonyl chloride)

2-Chloro-4-fluoro-5-nitrobenzene-1-sulfonyl chloride is a versatile sulfonylation reagent used in organic synthesis, particularly in the preparation of sulfonamides and sulfonate esters. Its key advantages include high reactivity due to the electron-withdrawing nitro and halogen substituents, which facilitate efficient nucleophilic substitution reactions. The compound’s well-defined structure and stability under controlled conditions make it suitable for precise functionalization in pharmaceutical and agrochemical intermediates. The presence of both chloro and fluoro groups enhances its utility in selective derivatization, while the nitro group further activates the sulfonyl chloride moiety for rapid conjugation. This reagent is particularly valuable in multistep synthetic routes requiring regioselective modifications.
2-chloro-4-fluoro-5-nitrobenzene-1-sulfonyl chloride structure
125607-05-8 structure
Product Name:2-chloro-4-fluoro-5-nitrobenzene-1-sulfonyl chloride
CAS No:125607-05-8
MF:C6H2Cl2FNO4S
MW:274.053781986237
CID:1218049
PubChem ID:11659109
Update Time:2025-06-07

2-chloro-4-fluoro-5-nitrobenzene-1-sulfonyl chloride Chemical and Physical Properties

Names and Identifiers

    • Benzenesulfonyl chloride, 2-chloro-4-fluoro-5-nitro-
    • 2-chloro-4-fluoro-5-nitrobenzenesulfonyl chloride
    • G44168
    • Z367452114
    • 2-chloro-4-fluoro-5-nitrobenzene-1-sulfonyl chloride
    • DTXSID60470184
    • AKOS030690070
    • EN300-36580
    • SCHEMBL9614718
    • 2-chloro-4-fluoro-5-nitrobenzene-1-sulfonylchloride
    • 125607-05-8
    • CS-0247413
    • Inchi: 1S/C6H2Cl2FNO4S/c7-3-1-4(9)5(10(11)12)2-6(3)15(8,13)14/h1-2H
    • InChI Key: QQYXMCLSCRSLQP-UHFFFAOYSA-N
    • SMILES: ClC1=CC(=C(C=C1S(=O)(=O)Cl)[N+](=O)[O-])F

Computed Properties

  • Exact Mass: 272.9065623g/mol
  • Monoisotopic Mass: 272.9065623g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 1
  • Complexity: 351
  • 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: 2.5
  • Topological Polar Surface Area: 88.3?2

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Additional information on 2-chloro-4-fluoro-5-nitrobenzene-1-sulfonyl chloride

Introduction to 2-chloro-4-fluoro-5-nitrobenzene-1-sulfonyl chloride (CAS No. 125607-05-8) and Its Applications in Modern Chemical Biology

2-chloro-4-fluoro-5-nitrobenzene-1-sulfonyl chloride, identified by the Chemical Abstracts Service Number (CAS No.) 125607-05-8, is a highly versatile sulfonating agent that has garnered significant attention in the field of chemical biology and pharmaceutical research. This compound belongs to a class of aromatic sulfonyl chlorides, which are widely utilized as intermediates in the synthesis of various biologically active molecules. The presence of multiple substituents—chloro, fluoro, and nitro groups—imparts unique reactivity and functional properties, making it a valuable tool for medicinal chemists and synthetic organic chemists.

The structural configuration of 2-chloro-4-fluoro-5-nitrobenzene-1-sulfonyl chloride imparts distinct electronic and steric characteristics that influence its reactivity. The electron-withdrawing nature of the nitro group and the electron-donating effects of the fluoro group create a balance that enhances its utility in cross-coupling reactions, sulfonation processes, and as a precursor for heterocyclic compound synthesis. This balance is particularly advantageous in constructing complex molecular frameworks essential for drug discovery.

In recent years, sulfonamide derivatives have emerged as pivotal scaffolds in the development of therapeutic agents targeting a wide range of diseases, including cancer, inflammation, and infectious disorders. The sulfonyl chloride functionality in 2-chloro-4-fluoro-5-nitrobenzene-1-sulfonyl chloride allows for facile introduction of sulfonamide linkages into target molecules through nucleophilic substitution reactions. This property has been leveraged in the synthesis of novel sulfonamides with enhanced pharmacological profiles.

One notable application of 2-chloro-4-fluoro-5-nitrobenzene-1-sulfonyl chloride is in the development of kinase inhibitors. Kinases are enzymes that play critical roles in cell signaling pathways, and their dysregulation is often associated with pathological conditions. By modifying existing kinase inhibitors with sulfonamide moieties derived from this compound, researchers have been able to improve binding affinity and selectivity. For instance, studies have demonstrated that derivatives of this compound exhibit potent inhibitory activity against specific kinases, which could lead to the development of more effective anticancer drugs.

The fluoro substituent in 2-chloro-4-fluoro-5-nitrobenzene-1-sulfonyl chloride is particularly noteworthy due to its significant impact on metabolic stability and pharmacokinetic properties of drug candidates. Fluorine atoms can enhance binding interactions within biological targets and modify drug solubility and bioavailability. This has led to an increased interest in fluorinated sulfonyl chlorides as building blocks for next-generation pharmaceuticals. Recent advances in fluorination techniques have further expanded the synthetic possibilities using this compound as a key intermediate.

Another area where 2-chloro-4-fluoro-5-nitrobenzene-1-sulfonyl chloride has made a significant impact is in the synthesis of protease inhibitors. Proteases are enzymes involved in various physiological processes, and their overactivity or misregulation can contribute to diseases such as Alzheimer's and HIV/AIDS. Researchers have utilized this compound to develop sulfonamides that inhibit specific proteases by forming stable covalent bonds with active site residues. These inhibitors have shown promise in preclinical studies, highlighting the importance of 2-chloro-4-fluoro-5-nitrobenzene-1-sulfonyl chloride as a synthetic precursor.

The nitro group in 2-chloro-4-fluoro-5-nitrobenzene-1-sulfonyl chloride also contributes to its utility in medicinal chemistry. Nitro groups can be reduced to amino groups under mild conditions, allowing for further functionalization of the aromatic ring. This redox-active property has been exploited in generating amino acid derivatives and other nitrogen-containing heterocycles that are prevalent in bioactive molecules. The ability to easily modify the nitro group makes this compound a flexible platform for exploring diverse chemical space.

In conclusion, 2-chloro-4-fluoro-5-nitrobenzene-1-sulfonyl chloride (CAS No. 125607-05-8) is a multifaceted sulfonating agent with broad applications in synthetic chemistry and drug discovery. Its unique structural features enable it to participate in various chemical transformations, making it an indispensable tool for researchers aiming to develop novel therapeutic agents. As our understanding of biological targets advances, the demand for specialized intermediates like this compound is expected to grow, driving further innovation in chemical biology.

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