Cas no 1339690-52-6 (1-Ethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride)

1-Ethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride is a versatile sulfonyl chloride derivative used as a key intermediate in organic synthesis, particularly in the preparation of sulfonamides and other functionalized pyrimidine compounds. Its reactive sulfonyl chloride group enables efficient coupling with amines and alcohols, facilitating the introduction of sulfonyl functionalities into target molecules. The ethyl and dioxo-tetrahydropyrimidine backbone provides structural stability while allowing further derivatization. This compound is valued for its high purity, consistent reactivity, and applicability in pharmaceutical and agrochemical research. Proper handling under anhydrous conditions is recommended due to its moisture sensitivity.
1-Ethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride structure
1339690-52-6 structure
Product Name:1-Ethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride
CAS No:1339690-52-6
MF:C6H7ClN2O4S
MW:238.648779153824
MDL:MFCD20361348
CID:5243468
PubChem ID:64339827
Update Time:2026-03-08

1-Ethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride Chemical and Physical Properties

Names and Identifiers

    • 1-ETHYL-2,4-DIOXO-1,2,3,4-TETRAHYDROPYRIMIDINE-5-SULFONYL CHLORIDE
    • 1-ETHYL-2,4-DIOXO-1,2,3,4-TETRAHYDROPYRIMIDINE-5-SULFONYLCHLORIDE
    • 5-Pyrimidinesulfonyl chloride, 1-ethyl-1,2,3,4-tetrahydro-2,4-dioxo-
    • 1-Ethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride
    • MDL: MFCD20361348
    • Inchi: 1S/C6H7ClN2O4S/c1-2-9-3-4(14(7,12)13)5(10)8-6(9)11/h3H,2H2,1H3,(H,8,10,11)
    • InChI Key: UWKBVQJCMCCMSV-UHFFFAOYSA-N
    • SMILES: ClS(C1C(NC(N(C=1)CC)=O)=O)(=O)=O

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 2
  • Complexity: 408
  • XLogP3: -0.3
  • Topological Polar Surface Area: 91.9

1-Ethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride Pricemore >>

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Additional information on 1-Ethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride

Recent Advances in the Application of 1-Ethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride (CAS: 1339690-52-6) in Chemical Biology and Pharmaceutical Research

The compound 1-Ethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride (CAS: 1339690-52-6) has recently emerged as a critical intermediate in the synthesis of novel bioactive molecules, particularly in the fields of chemical biology and pharmaceutical research. This sulfonyl chloride derivative is characterized by its high reactivity, making it a versatile building block for the development of sulfonamide-based compounds, which are widely recognized for their therapeutic potential. Recent studies have highlighted its utility in the design of enzyme inhibitors, antimicrobial agents, and anticancer drugs, underscoring its significance in drug discovery and development.

One of the most notable applications of 1-Ethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride is its role in the synthesis of sulfonamide-based enzyme inhibitors. Sulfonamides are known to interact with a variety of enzymes, including carbonic anhydrases and proteases, which are implicated in numerous pathological conditions. A 2023 study published in the Journal of Medicinal Chemistry demonstrated the efficacy of derivatives synthesized from this compound in inhibiting carbonic anhydrase IX, a target for anticancer therapy. The study reported a significant reduction in tumor growth in preclinical models, suggesting the potential of these derivatives as lead compounds for further development.

In addition to its applications in enzyme inhibition, this compound has also been explored for its antimicrobial properties. A recent investigation published in Bioorganic & Medicinal Chemistry Letters (2024) described the synthesis of a series of sulfonamide derivatives using 1-Ethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride as a key intermediate. These derivatives exhibited potent activity against a range of Gram-positive and Gram-negative bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and Escherichia coli. The researchers attributed this activity to the ability of the sulfonamide moiety to disrupt bacterial cell wall synthesis, highlighting the compound's potential in addressing antibiotic resistance.

Another area of interest is the use of this sulfonyl chloride in the development of anticancer agents. A 2024 study in the European Journal of Medicinal Chemistry reported the synthesis of novel pyrimidine-sulfonamide hybrids, which demonstrated selective cytotoxicity against various cancer cell lines, including breast and lung cancer. The study emphasized the role of the sulfonyl chloride group in enhancing the compounds' binding affinity to target proteins, thereby improving their therapeutic efficacy. These findings open new avenues for the design of targeted cancer therapies with reduced side effects.

Despite its promising applications, the handling and storage of 1-Ethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride require careful consideration due to its reactive nature. Recent advancements in synthetic methodologies have focused on optimizing reaction conditions to improve yield and purity while minimizing degradation. For instance, a 2023 publication in Organic Process Research & Development outlined a scalable synthesis protocol that employs mild conditions and environmentally friendly solvents, addressing some of the challenges associated with large-scale production.

In conclusion, 1-Ethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride (CAS: 1339690-52-6) represents a valuable tool in chemical biology and pharmaceutical research, with diverse applications ranging from enzyme inhibition to antimicrobial and anticancer drug development. Ongoing research continues to uncover new possibilities for this compound, driven by its unique chemical properties and therapeutic potential. Future studies are expected to further elucidate its mechanisms of action and explore its utility in other therapeutic areas, solidifying its role in modern drug discovery.

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