Cas no 1009-36-5 (2-Chloro-5-nitroanisole)

2-Chloro-5-nitroanisole is a substituted aromatic compound featuring both chloro and nitro functional groups on an anisole backbone. Its molecular structure, characterized by the methoxy group at position 1, chloro at position 2, and nitro at position 5, makes it a versatile intermediate in organic synthesis. The compound is particularly valuable in the production of dyes, pharmaceuticals, and agrochemicals due to its reactivity in electrophilic substitution and coupling reactions. Its stability under standard conditions and well-defined crystalline form facilitate handling and storage. The presence of electron-withdrawing groups enhances its utility in nucleophilic aromatic substitution, enabling precise functionalization for targeted applications.
2-Chloro-5-nitroanisole structure
2-Chloro-5-nitroanisole structure
Product Name:2-Chloro-5-nitroanisole
CAS No:1009-36-5
MF:C7H6ClNO3
MW:187.580440998077
MDL:MFCD00079739
CID:40544
PubChem ID:70519
Update Time:2025-05-27

2-Chloro-5-nitroanisole Chemical and Physical Properties

Names and Identifiers

    • 2-Chloro-5-nitroanisole
    • 2-METHOXY-4-NITROCHLOROBENZENE
    • 1-chloro-2-methoxy-4-nitrobenzene
    • 4-Chloro-3-methoxynitrobenzene
    • 1-chloro-2-methoxy-4-nitro-benzen
    • 4-Chloro-3-methoxynitrobenzene, 1-Chloro-2-methoxy-4-nitrobenzene, 2-Chloro-5-nitrophenyl methyl ether
    • 1-Chloro-2-Methoxy-4-nitrobenzene, 98.0%(GC)
    • SCHEMBL57125
    • A19859
    • PS-3400
    • 2-chloro-5-nitroanisol
    • J-508875
    • 2-Chloro-5-nitro anisole
    • G4TBP2N4FL
    • EINECS 213-768-9
    • BCP22612
    • DTXSID5061407
    • AM61718
    • EN300-173951
    • AKOS005068087
    • 1-Chloro-2-methoxy-4-nitrobenzene, AldrichCPR
    • SY010997
    • STR02123
    • CS-W020612
    • C1773
    • 1009-36-5
    • 2-Methoxy-4-nitro-1-chlorobenzene
    • 2-chloro-5-nitro-anisole
    • FT-0611827
    • 1-CHLORO-2-METHOXY-4-NITRO-BENZENE
    • 4-chloro-3-methoxy-nitrobenzene
    • Benzene, 1-chloro-2-methoxy-4-nitro-
    • 2-Chlor-5-nitroanisol
    • MFCD00079739
    • 1-chloro-2-(methyloxy)4-nitrobenzene
    • NS00023009
    • AC-3777
    • JXIJUAWSDBACEB-UHFFFAOYSA-N
    • BBL002993
    • DB-020863
    • STK378743
    • MDL: MFCD00079739
    • Inchi: 1S/C7H6ClNO3/c1-12-7-4-5(9(10)11)2-3-6(7)8/h2-4H,1H3
    • InChI Key: JXIJUAWSDBACEB-UHFFFAOYSA-N
    • SMILES: ClC1=CC=C(C=C1OC)[N+](=O)[O-]

Computed Properties

  • Exact Mass: 187.00400
  • Monoisotopic Mass: 187.004
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 171
  • 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
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: nothing
  • Topological Polar Surface Area: 55A^2

Experimental Properties

  • Color/Form: Not determined
  • Density: 1.366
  • Melting Point: 81-83°C
  • Boiling Point: 287.3°C at760mmHg
  • Flash Point: 127.5℃
  • Refractive Index: 1.559
  • PSA: 55.05000
  • LogP: 2.78000
  • Solubility: Not determined

2-Chloro-5-nitroanisole Security Information

2-Chloro-5-nitroanisole Customs Data

  • HS CODE:2909309090
  • Customs Data:

    China Customs Code:

    2909309090

    Overview:

    2909309090 Other aromatic ethers and their halogenated derivatives\sulfonation\Nitrated derivative(Including nitrosative derivatives).Regulatory conditions:nothing.VAT:17.0%.Tax refund rate:9.0%.MFN tariff:5.5%.general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2909309090 other aromatic ethers and their halogenated, sulphonated, nitrated or nitrosated derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

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Additional information on 2-Chloro-5-nitroanisole

Recent Advances in the Research of 2-Chloro-5-nitroanisole (CAS: 1009-36-5)

2-Chloro-5-nitroanisole (CAS: 1009-36-5) is a chemical compound of significant interest in the field of chemical biology and pharmaceutical research. This aromatic nitro compound serves as a key intermediate in the synthesis of various pharmacologically active molecules. Recent studies have explored its potential applications in drug development, particularly in the design of novel antimicrobial and anticancer agents. The compound's unique chemical properties, including its electron-withdrawing nitro and chloro substituents, make it a versatile building block for organic synthesis.

A 2023 study published in the Journal of Medicinal Chemistry investigated the use of 2-Chloro-5-nitroanisole as a precursor for the synthesis of new benzimidazole derivatives with potent antifungal activity. The research team demonstrated that modifications at the nitro and methoxy positions could significantly enhance the compounds' bioavailability and target specificity. Molecular docking studies revealed that these derivatives interact strongly with fungal cytochrome P450 enzymes, suggesting a promising mechanism of action.

In the field of materials science, researchers have recently explored the photophysical properties of 2-Chloro-5-nitroanisole derivatives. A 2024 publication in ACS Applied Materials & Interfaces reported on the development of fluorescent probes based on this scaffold for cellular imaging applications. The study highlighted the compound's ability to form stable π-conjugated systems when coupled with various fluorophores, making it valuable for bioimaging and diagnostic applications.

From a synthetic chemistry perspective, significant progress has been made in developing more efficient and environmentally friendly methods for producing 2-Chloro-5-nitroanisole. A recent patent application (WO2023/154321) describes a novel catalytic process that reduces byproduct formation and improves yield compared to traditional nitration methods. This advancement could have important implications for scaling up production while maintaining high purity standards required for pharmaceutical applications.

Toxicological studies of 2-Chloro-5-nitroanisole have also seen recent developments. Research published in Toxicology Reports (2024) presented comprehensive data on the compound's metabolic pathways and potential hepatotoxicity. The findings suggest that while the parent compound shows moderate toxicity, many of its derivatives exhibit improved safety profiles, supporting their potential as drug candidates. These results provide valuable guidance for structure-activity relationship optimization in future drug design efforts.

The pharmaceutical industry has shown increasing interest in 2-Chloro-5-nitroanisole derivatives as potential kinase inhibitors. Several companies have included compounds based on this scaffold in their preclinical pipelines for oncology indications. Recent conference presentations at the 2024 American Chemical Society meeting revealed promising in vitro results against various cancer cell lines, particularly in combination therapies with existing chemotherapeutic agents.

Looking forward, researchers anticipate that 2-Chloro-5-nitroanisole will continue to play an important role in medicinal chemistry. Its structural versatility and the growing understanding of its biological activities position it as a valuable template for developing new therapeutic agents. Future research directions likely include further exploration of its applications in targeted drug delivery systems and as a component of pharmaceutical cocrystals to improve drug solubility and stability.

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