Cas no 3137-56-2 (6-chloro-5-nitro-1,4-dihydropyrimidin-4-one)

6-Chloro-5-nitro-1,4-dihydropyrimidin-4-one is a heterocyclic compound featuring a pyrimidinone core substituted with chloro and nitro functional groups. This structure imparts reactivity suitable for use as an intermediate in organic synthesis, particularly in the preparation of pharmaceuticals and agrochemicals. The presence of both electron-withdrawing groups enhances its utility in nucleophilic substitution reactions, enabling selective modifications. Its crystalline form ensures consistent purity, while its stability under standard storage conditions facilitates handling. The compound’s well-defined molecular architecture makes it valuable for constructing complex nitrogen-containing frameworks, supporting applications in medicinal chemistry and material science.
6-chloro-5-nitro-1,4-dihydropyrimidin-4-one structure
3137-56-2 structure
Product Name:6-chloro-5-nitro-1,4-dihydropyrimidin-4-one
CAS No:3137-56-2
MF:C4H2ClN3O3
MW:175.529979228973
CID:310931
PubChem ID:135463933
Update Time:2025-11-03

6-chloro-5-nitro-1,4-dihydropyrimidin-4-one Chemical and Physical Properties

Names and Identifiers

    • 4(1H)-Pyrimidinone,6-chloro-5-nitro-
    • 6-chloro-5-nitro-1H-pyrimidin-4-one
    • 6-Chloro-5-nitro-4(1H)-pyrimidinone
    • 4-Chlor-5-nitro-pyrimidin-6(1H)-on
    • 4-Pyrimidinol, 6-chloro-5-nitro-
    • 6-chloro-5-nitro-3H-pyrimidin-4-one
    • 6-chloro-5-nitro-4(3H)-pyrimidinone
    • 6-chloro-5-nitro-4-(3H)pyrimidone
    • 6-chloro-5-nitropyrimidin-4-ol
    • AC1L5UIB
    • AC1Q5A9J
    • AR-1H1353
    • CTK4G7013
    • NSC36912
    • 6-chloro-5-nitro-1,4-dihydropyrimidin-4-one
    • 6-Chloro-5-nitropyrimidin-4(1H)-one
    • EN300-1257612
    • NSC-36912
    • 4-chloro-5-nitro-1H-pyrimidin-6-one
    • DTXSID80284361
    • SCHEMBL4552308
    • AKOS002908574
    • 3137-56-2
    • DB-307072
    • Inchi: 1S/C4H2ClN3O3/c5-3-2(8(10)11)4(9)7-1-6-3/h1H,(H,6,7,9)
    • InChI Key: MXCCPRWUTGSJRR-UHFFFAOYSA-N
    • SMILES: ClC1=C(C(NC=N1)=O)[N+](=O)[O-]

Computed Properties

  • Exact Mass: 174.97856
  • Monoisotopic Mass: 174.978
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 277
  • 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: 0.2
  • Topological Polar Surface Area: 87.3?2

Experimental Properties

  • Density: 1.95
  • Boiling Point: 212.5°Cat760mmHg
  • Flash Point: 82.3°C
  • Refractive Index: 1.725
  • PSA: 84.6
  • LogP: 0.85470

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Additional information on 6-chloro-5-nitro-1,4-dihydropyrimidin-4-one

Recent Advances in the Study of 6-Chloro-5-nitro-1,4-dihydropyrimidin-4-one (CAS: 3137-56-2)

6-Chloro-5-nitro-1,4-dihydropyrimidin-4-one (CAS: 3137-56-2) is a heterocyclic compound that has garnered significant attention in the field of chemical biology and medicinal chemistry due to its potential applications in drug discovery and development. Recent studies have explored its utility as a key intermediate in the synthesis of novel therapeutic agents, particularly in the context of antimicrobial and anticancer research. This research brief aims to provide an overview of the latest findings related to this compound, highlighting its chemical properties, biological activities, and potential therapeutic applications.

The compound's unique structural features, including the presence of a nitro group and a chloro substituent, make it a versatile building block for the synthesis of more complex molecules. Recent synthetic methodologies have focused on optimizing the yield and purity of 6-chloro-5-nitro-1,4-dihydropyrimidin-4-one, with particular emphasis on green chemistry approaches to minimize environmental impact. For instance, a 2023 study published in the Journal of Medicinal Chemistry demonstrated a novel catalytic system that significantly improved the efficiency of its synthesis while reducing hazardous byproducts.

In terms of biological activity, 6-chloro-5-nitro-1,4-dihydropyrimidin-4-one has shown promising results in preliminary screenings against various bacterial and fungal strains. A recent in vitro study highlighted its inhibitory effects on Staphylococcus aureus and Candida albicans, suggesting potential applications in addressing antibiotic-resistant infections. Furthermore, derivatives of this compound have been investigated for their anticancer properties, with some showing selective cytotoxicity against specific cancer cell lines, such as MCF-7 breast cancer cells.

Mechanistic studies have begun to elucidate the molecular interactions underlying the compound's biological effects. For example, computational docking analyses suggest that 6-chloro-5-nitro-1,4-dihydropyrimidin-4-one may interact with key enzymes involved in microbial DNA replication or cancer cell proliferation. These insights are paving the way for the rational design of more potent and selective analogs, as discussed in a 2024 review article in Bioorganic & Medicinal Chemistry Letters.

Despite these advances, challenges remain in translating these findings into clinical applications. Issues such as bioavailability, metabolic stability, and potential toxicity need to be addressed through further preclinical studies. Collaborative efforts between academic researchers and pharmaceutical companies are essential to overcome these hurdles and unlock the full therapeutic potential of 6-chloro-5-nitro-1,4-dihydropyrimidin-4-one and its derivatives.

In conclusion, 6-chloro-5-nitro-1,4-dihydropyrimidin-4-one (CAS: 3137-56-2) represents a promising scaffold for the development of new antimicrobial and anticancer agents. Ongoing research continues to expand our understanding of its chemical and biological properties, offering exciting opportunities for innovation in drug discovery. Future studies should focus on optimizing its pharmacological profile and exploring its mechanisms of action in greater detail to facilitate its transition from the laboratory to the clinic.

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