Cas no 57807-27-9 (1-cyclopropyl-4-iodobenzene)

1-Cyclopropyl-4-iodobenzene is a halogenated aromatic compound featuring a cyclopropyl substituent and an iodine atom on the benzene ring. This structure makes it a versatile intermediate in organic synthesis, particularly in cross-coupling reactions such as Suzuki-Miyaura and Negishi couplings, where the iodine acts as an excellent leaving group. The cyclopropyl moiety enhances steric and electronic properties, enabling applications in pharmaceuticals, agrochemicals, and material science. Its stability and reactivity profile make it suitable for constructing complex molecular frameworks. The compound is typically handled under inert conditions due to sensitivity to light and moisture. High purity grades are available for precision synthetic applications.
1-cyclopropyl-4-iodobenzene structure
1-cyclopropyl-4-iodobenzene structure
Product Name:1-cyclopropyl-4-iodobenzene
CAS No:57807-27-9
MF:C9H9I
MW:244.072234869003
CID:344081
PubChem ID:3263814
Update Time:2025-10-30

1-cyclopropyl-4-iodobenzene Chemical and Physical Properties

Names and Identifiers

    • Benzene, 1-cyclopropyl-4-iodo-
    • 1-cyclopropyl-4-iodobenzene
    • FT-0753346
    • 57807-27-9
    • EN300-1722985
    • SCHEMBL3453587
    • DTXSID90390801
    • CS-0312366
    • G76151
    • DA-04707
    • Inchi: 1S/C9H9I/c10-9-5-3-8(4-6-9)7-1-2-7/h3-7H,1-2H2
    • InChI Key: AFDRVFGCDMLCKR-UHFFFAOYSA-N
    • SMILES: IC1C=CC(=CC=1)C1CC1

Computed Properties

  • Exact Mass: 243.97447
  • Monoisotopic Mass: 243.97490g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 0
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 1
  • Complexity: 110
  • 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: 3.5
  • Topological Polar Surface Area: 0?2

Experimental Properties

  • PSA: 0

1-cyclopropyl-4-iodobenzene Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
Enamine
EN300-1722985-0.05g
1-cyclopropyl-4-iodobenzene
57807-27-9 95%
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$245.0 2023-09-20
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1PlusChem
1P00EOLJ-50mg
BENZENE, 1-CYCLOPROPYL-4-IODO-
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$354.00 2023-12-16
1PlusChem
1P00EOLJ-100mg
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1-cyclopropyl-4-iodobenzene Related Literature

Additional information on 1-cyclopropyl-4-iodobenzene

Recent Advances in the Application of 1-Cyclopropyl-4-Iodobenzene (57807-27-9) in Chemical and Pharmaceutical Research

1-Cyclopropyl-4-iodobenzene (CAS: 57807-27-9) has recently emerged as a key intermediate in the synthesis of novel pharmaceutical compounds and bioactive molecules. This aromatic iodide, characterized by its cyclopropyl substituent, has garnered significant attention due to its versatility in cross-coupling reactions and its potential applications in drug discovery. Recent studies have explored its role in the development of targeted therapies, particularly in oncology and infectious diseases, highlighting its importance in modern medicinal chemistry.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the utility of 1-cyclopropyl-4-iodobenzene in the synthesis of potent kinase inhibitors. Researchers utilized this compound as a building block in Suzuki-Miyaura cross-coupling reactions to create a series of novel compounds with enhanced selectivity for specific kinase targets. The study reported improved pharmacokinetic properties and reduced off-target effects compared to previous generations of inhibitors, suggesting promising clinical applications.

In the field of antimicrobial research, a team from the University of Cambridge recently employed 1-cyclopropyl-4-iodobenzene in the development of new quinolone derivatives. Their work, published in Antimicrobial Agents and Chemotherapy, showed that incorporation of this moiety led to compounds with improved activity against drug-resistant bacterial strains, particularly MRSA and ESBL-producing Enterobacteriaceae. The researchers attributed this enhanced activity to the unique steric and electronic properties imparted by the cyclopropyl group.

Recent advancements in synthetic methodology have also expanded the applications of 1-cyclopropyl-4-iodobenzene. A 2024 Nature Chemistry publication detailed a novel photoredox-catalyzed arylation protocol using this compound, enabling more efficient construction of complex molecular architectures under mild conditions. This breakthrough has significant implications for the synthesis of pharmaceutical compounds, particularly those containing sensitive functional groups that might not survive traditional coupling conditions.

From a safety and regulatory perspective, recent toxicological studies have confirmed the favorable profile of 1-cyclopropyl-4-iodobenzene as a synthetic intermediate. The European Chemicals Agency's 2023 assessment noted its relatively low acute toxicity and good stability under standard handling conditions, making it an attractive choice for industrial-scale pharmaceutical production. However, researchers emphasize the importance of proper handling due to its potential iodine-related reactivity.

Looking forward, the unique properties of 1-cyclopropyl-4-iodobenzene position it as a valuable tool in the development of next-generation therapeutics. Its combination of synthetic versatility and the pharmacologically beneficial cyclopropyl moiety suggests continued importance in drug discovery programs. Ongoing research is exploring its use in PROTACs (proteolysis targeting chimeras) and other targeted protein degradation platforms, potentially opening new avenues for the treatment of previously "undruggable" targets.

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