Cas no 2228838-85-3 (1-(3,5-dichloropyridin-4-yl)cyclopropane-1-carbaldehyde)

1-(3,5-Dichloropyridin-4-yl)cyclopropane-1-carbaldehyde is a specialized organic compound featuring a cyclopropane ring fused to a dichloropyridine moiety, with a formyl functional group at the cyclopropane position. This structure imparts unique reactivity, making it valuable as an intermediate in pharmaceutical and agrochemical synthesis. The presence of both electron-withdrawing chlorine atoms and the aldehyde group enhances its utility in cross-coupling reactions, nucleophilic additions, and cyclization processes. Its rigid cyclopropane scaffold contributes to steric specificity, enabling precise molecular modifications. The compound is typically handled under controlled conditions due to its reactive aldehyde group, ensuring stability and purity for high-yield applications in complex synthetic pathways.
1-(3,5-dichloropyridin-4-yl)cyclopropane-1-carbaldehyde structure
2228838-85-3 structure
Product Name:1-(3,5-dichloropyridin-4-yl)cyclopropane-1-carbaldehyde
CAS No:2228838-85-3
MF:C9H7Cl2NO
MW:216.063980340958
CID:5973391
PubChem ID:165634337
Update Time:2025-05-23

1-(3,5-dichloropyridin-4-yl)cyclopropane-1-carbaldehyde Chemical and Physical Properties

Names and Identifiers

    • 1-(3,5-dichloropyridin-4-yl)cyclopropane-1-carbaldehyde
    • EN300-1975120
    • 2228838-85-3
    • Inchi: 1S/C9H7Cl2NO/c10-6-3-12-4-7(11)8(6)9(5-13)1-2-9/h3-5H,1-2H2
    • InChI Key: WZMYOMBRDMVZPU-UHFFFAOYSA-N
    • SMILES: ClC1C=NC=C(C=1C1(C=O)CC1)Cl

Computed Properties

  • Exact Mass: 214.9904692g/mol
  • Monoisotopic Mass: 214.9904692g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 208
  • 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: 1.9
  • Topological Polar Surface Area: 30?2

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Additional information on 1-(3,5-dichloropyridin-4-yl)cyclopropane-1-carbaldehyde

1-(3,5-Dichloropyridin-4-yl)cyclopropane-1-carbaldehyde (CAS No. 2228838-85-3)

1-(3,5-Dichloropyridin-4-yl)cyclopropane-1-carbaldehyde is a highly specialized organic compound with the CAS registry number 2228838-85-3. This compound has garnered significant attention in the fields of organic chemistry and pharmacology due to its unique structural features and potential applications in drug development. The molecule consists of a cyclopropane ring fused with a pyridine ring, substituted with two chlorine atoms at the 3 and 5 positions, and an aldehyde group at the 4 position of the pyridine ring. This combination of functional groups and aromaticity makes it a versatile compound with promising properties for various chemical and biological applications.

The synthesis of 1-(3,5-Dichloropyridin-4-yl)cyclopropane-1-carbaldehyde involves a series of intricate chemical reactions, including Friedel-Crafts alkylation, cyclization, and oxidation processes. Recent advancements in catalytic methods have enabled the efficient production of this compound with high purity and yield. Researchers have also explored its reactivity under different conditions, revealing its potential as an intermediate in the synthesis of more complex molecules.

One of the most notable aspects of this compound is its cyclopropane ring, which introduces significant ring strain and enhances its reactivity. This feature has been exploited in various chemical transformations, such as [2+1] cycloadditions and other pericyclic reactions. The presence of the aldehyde group further increases its versatility, allowing for participation in condensation reactions like the aldol reaction or as a precursor for imine formation.

Recent studies have highlighted the potential of 1-(3,5-Dichloropyridin-4-yl)cyclopropane-1-carbaldehyde in medicinal chemistry. Its ability to act as a scaffold for constructing bioactive molecules has been demonstrated in several research papers. For instance, scientists have reported its use as a building block for designing inhibitors of key enzymes involved in cancer progression. The compound's unique electronic properties and steric effects make it an ideal candidate for modulating protein-ligand interactions.

In addition to its synthetic applications, this compound has shown promise in materials science. Its ability to form stable coordination complexes with transition metals has led to investigations into its use as a ligand in catalytic systems. Researchers have also explored its potential as a component in organic electronics, where its aromaticity and conjugation could contribute to novel electronic properties.

The physical properties of 1-(3,5-Dichloropyridin-4-yl)cyclopropane-1-carbaldehyde are well-documented. It has a melting point of approximately 170°C and is sparingly soluble in water but highly soluble in organic solvents such as dichloromethane and ethyl acetate. These properties make it suitable for various analytical techniques, including chromatography and spectroscopy.

From an environmental perspective, studies have been conducted to assess the biodegradability and toxicity of this compound. Preliminary results suggest that it undergoes slow degradation under aerobic conditions but poses minimal acute toxicity to aquatic organisms at concentrations typically encountered in industrial settings.

In conclusion, 1-(3,5-Dichloropyridin-4-yl)cyclopropane-1-carbaldehyde (CAS No. 2228838-85) is a multifaceted compound with applications spanning organic synthesis, medicinal chemistry, and materials science. Its unique structure and reactivity continue to inspire innovative research directions, making it a valuable addition to the arsenal of modern chemical compounds.

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