Cas no 58142-97-5 (1-chloro-5-nitroisoquinoline)

1-Chloro-5-nitroisoquinoline is a halogenated nitro-substituted isoquinoline derivative with significant utility in organic synthesis and pharmaceutical research. Its reactive chloro and nitro functional groups make it a versatile intermediate for nucleophilic substitution reactions, enabling the construction of complex heterocyclic frameworks. The electron-withdrawing nitro group enhances electrophilicity at the chloro position, facilitating selective derivatization. This compound is particularly valuable in medicinal chemistry for the development of bioactive molecules, including potential kinase inhibitors and antimicrobial agents. Its crystalline solid form ensures stability under standard storage conditions, while its well-defined reactivity profile allows for predictable transformations in multi-step syntheses. Suitable for controlled functionalization, it serves as a key building block in targeted molecular design.
1-chloro-5-nitroisoquinoline structure
1-chloro-5-nitroisoquinoline structure
Product Name:1-chloro-5-nitroisoquinoline
CAS No:58142-97-5
MF:C9H5ClN2O2
MW:208.601200819016
MDL:MFCD11052590
CID:838664
PubChem ID:459774
Update Time:2025-06-08

1-chloro-5-nitroisoquinoline Chemical and Physical Properties

Names and Identifiers

    • 1-chloro-5-nitroisoquinoline
    • 1-Chloro-5-nitro-isoquinoline
    • SCHEMBL2379102
    • EN300-247823
    • DB-072434
    • ABMIIJPKPFSMLK-UHFFFAOYSA-N
    • SB37785
    • DS-0589
    • MFCD11052590
    • 1-Chloro-5-nitroisoquinoline;Abbypharma ap-12-10923;
    • J-504522
    • CS-0097914
    • AKOS005257902
    • SY043271
    • CL1004
    • Isoquinoline, 1-chloro-5-nitro-
    • DTXSID30332700
    • AC-23253
    • 58142-97-5
    • MDL: MFCD11052590
    • Inchi: 1S/C9H5ClN2O2/c10-9-7-2-1-3-8(12(13)14)6(7)4-5-11-9/h1-5H
    • InChI Key: ABMIIJPKPFSMLK-UHFFFAOYSA-N
    • SMILES: ClC1C2C=CC=C(C=2C=CN=1)[N+](=O)[O-]

Computed Properties

  • Exact Mass: 208.00400
  • Monoisotopic Mass: 208.0039551g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 1
  • Complexity: 231
  • 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: 2.9
  • Topological Polar Surface Area: 58.7?2

Experimental Properties

  • Color/Form: Pale-yellow to Yellow-brown Solid
  • Density: 1.484
  • Melting Point: 183-184 oC
  • PSA: 58.71000
  • LogP: 3.31960

1-chloro-5-nitroisoquinoline Security Information

1-chloro-5-nitroisoquinoline Customs Data

  • HS CODE:2933499090
  • Customs Data:

    China Customs Code:

    2933499090

    Overview:

    2933499090. Other compounds containing quinoline or isoquinoline ring system [but not further fused]. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933499090. other compounds containing in the structure a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

1-chloro-5-nitroisoquinoline Pricemore >>

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1-chloro-5-nitroisoquinoline Production Method

Additional information on 1-chloro-5-nitroisoquinoline

Recent Advances in the Application of 1-Chloro-5-nitroisoquinoline (CAS: 58142-97-5) in Chemical Biology and Pharmaceutical Research

1-Chloro-5-nitroisoquinoline (CAS: 58142-97-5) is a heterocyclic compound that has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound serves as a key intermediate in the synthesis of various biologically active molecules, particularly those targeting kinase inhibition and anticancer therapies. Recent studies have explored its potential as a scaffold for developing novel therapeutic agents, leveraging its unique chemical properties and reactivity.

A 2023 study published in the Journal of Medicinal Chemistry highlighted the role of 1-chloro-5-nitroisoquinoline in the design of selective kinase inhibitors. Researchers utilized this compound as a starting material to synthesize a series of derivatives, which were then evaluated for their inhibitory activity against a panel of kinases. The results demonstrated that certain derivatives exhibited potent and selective inhibition of specific kinase targets, suggesting their potential as lead compounds for further drug development.

In addition to its applications in kinase inhibition, 1-chloro-5-nitroisoquinoline has also been investigated for its role in anticancer drug discovery. A recent study in Bioorganic & Medicinal Chemistry Letters reported the synthesis of novel isoform-selective PI3K inhibitors using this compound as a core structure. The researchers found that the nitro and chloro functional groups on the isoquinoline ring played a critical role in modulating the binding affinity and selectivity of the inhibitors, leading to improved therapeutic profiles.

Another area of interest is the use of 1-chloro-5-nitroisoquinoline in the development of fluorescent probes for biological imaging. A 2024 publication in Chemical Communications described the synthesis of a fluorescent derivative of this compound, which exhibited strong emission properties and was used to visualize cellular processes in real-time. This application underscores the compound's versatility beyond traditional drug discovery, extending into the realm of diagnostic tools and imaging agents.

Despite these promising developments, challenges remain in optimizing the pharmacokinetic and safety profiles of 1-chloro-5-nitroisoquinoline-based compounds. Recent research has focused on addressing these issues through structural modifications and formulation strategies. For instance, a 2023 study in Molecular Pharmaceutics explored the use of nanoparticle-based delivery systems to enhance the bioavailability and reduce the toxicity of these compounds, paving the way for their clinical translation.

In conclusion, 1-chloro-5-nitroisoquinoline (CAS: 58142-97-5) continues to be a valuable scaffold in chemical biology and pharmaceutical research. Its applications span from kinase inhibition and anticancer drug discovery to biological imaging, demonstrating its broad utility. Ongoing research aims to further refine its derivatives and delivery systems, ensuring their efficacy and safety for therapeutic use. As the field advances, this compound is expected to play an increasingly important role in the development of next-generation pharmaceuticals.

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