Cas no 903551-23-5 (4,6-Dichloroindoline)

4,6-Dichloroindoline is a halogenated indoline derivative primarily used as an intermediate in organic synthesis and pharmaceutical research. Its key structural features include a dichloro-substituted indoline core, which enhances reactivity in electrophilic and nucleophilic substitution reactions. This compound is valued for its versatility in constructing complex heterocyclic frameworks, particularly in the development of bioactive molecules and agrochemicals. The presence of chlorine atoms at the 4- and 6-positions offers selective functionalization opportunities, making it a useful precursor for tailored synthetic applications. High purity grades ensure consistent performance in research and industrial processes. Proper handling is advised due to its potential sensitivity to light and moisture.
4,6-Dichloroindoline structure
4,6-Dichloroindoline structure
Product Name:4,6-Dichloroindoline
CAS No:903551-23-5
MF:C8H7Cl2N
MW:188.053879976273
CID:797651
PubChem ID:16244448
Update Time:2025-09-28

4,6-Dichloroindoline Chemical and Physical Properties

Names and Identifiers

    • 4,6-Dichloroindoline
    • 1H-Indole,4,6-dichloro-2,3-dihydro-
    • 4,6-DICHLORO-2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE
    • 4,6-DICHLOROINDOLINE HYDROCHLORIDE
    • 4,6-dichloro-2,3-dihydro-1h-indole
    • A860833
    • EN300-1145533
    • 903551-23-5
    • SCHEMBL1877071
    • SB64380
    • CS-0271919
    • KXKGRTPNRAYWNZ-UHFFFAOYSA-N
    • AKOS009133006
    • G73615
    • DA-01291
    • Inchi: 1S/C8H7Cl2N/c9-5-3-7(10)6-1-2-11-8(6)4-5/h3-4,11H,1-2H2
    • InChI Key: KXKGRTPNRAYWNZ-UHFFFAOYSA-N
    • SMILES: ClC1=CC(=CC2=C1CCN2)Cl

Computed Properties

  • Exact Mass: 222.97200
  • Monoisotopic Mass: 222.972
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 151
  • Covalently-Bonded Unit Count: 2
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 12A^2
  • XLogP3: 3.2

Experimental Properties

  • PSA: 12.03000
  • LogP: 3.90140

4,6-Dichloroindoline Customs Data

  • HS CODE:2933990090
  • Customs Data:

    China Customs Code:

    2933990090

    Overview:

    2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. 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:

    2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

4,6-Dichloroindoline Pricemore >>

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Additional information on 4,6-Dichloroindoline

Introduction to 4,6-Dichloroindoline (CAS No: 903551-23-5)

4,6-Dichloroindoline, with the chemical formula C8H5Cl2N and CAS number 903551-23-5, is a significant intermediate in modern pharmaceutical and chemical synthesis. This compound has garnered considerable attention due to its versatile applications in the development of bioactive molecules and functional materials. The presence of two chlorine substituents at the 4th and 6th positions on the indoline ring enhances its reactivity, making it a valuable building block for further derivatization.

The indoline core is a privileged scaffold in medicinal chemistry, known for its ability to form stable hydrogen bonds and interact with biological targets. The introduction of chlorine atoms at specific positions modifies its electronic and steric properties, enabling tailored interactions with enzymes and receptors. Recent studies have highlighted the utility of 4,6-Dichloroindoline in designing novel therapeutic agents, particularly in the realms of oncology and anti-inflammatory treatments.

In the context of drug discovery, 4,6-Dichloroindoline serves as a precursor for synthesizing small-molecule inhibitors. Its structural framework allows for modifications that can optimize pharmacokinetic profiles and target specificity. For instance, researchers have leveraged this compound to develop kinase inhibitors, which are crucial in treating cancers by disrupting aberrant signaling pathways. The dichloro substitution pattern facilitates further functionalization, enabling the attachment of pharmacophores that enhance binding affinity.

One of the most compelling aspects of 4,6-Dichloroindoline is its role in material science applications. The indoline structure contributes to its aromaticity and thermal stability, making it suitable for use in organic electronics and light-emitting diodes (OLEDs). Recent advancements have demonstrated its incorporation into polymer matrices to improve charge transport properties. This dual functionality—pharmaceutical relevance and material science utility—underscores the compound's importance as a cross-disciplinary tool.

The synthesis of 4,6-Dichloroindoline typically involves chlorination reactions on an indoline precursor. Advances in catalytic methods have enabled more efficient and selective preparations, reducing byproduct formation. These improvements align with the growing emphasis on green chemistry principles, where minimizing waste and energy consumption are paramount. The optimization of synthetic routes not only enhances scalability but also ensures cost-effectiveness for industrial applications.

From a biological perspective, 4,6-Dichloroindoline derivatives have shown promise in modulating various biological processes. For example, certain analogs exhibit inhibitory effects on cytochrome P450 enzymes, which are involved in drug metabolism. Understanding these interactions is critical for predicting drug-drug interactions and designing safer therapeutic regimens. Computational modeling has further accelerated the discovery process by allowing virtual screening of potential derivatives before experimental synthesis.

The compound's reactivity also makes it a valuable tool in biochemical assays. Researchers utilize 4,6-Dichloroindoline-based probes to study enzyme mechanisms and protein-protein interactions. These probes can be designed to covalently label target molecules, providing insights into their function within cellular pathways. Such methodologies are essential for elucidating complex biological networks and identifying novel therapeutic targets.

Looking ahead, the future applications of 4,6-Dichloroindoline are likely to expand with ongoing research. Innovations in synthetic chemistry may unlock new derivatives with enhanced properties, while interdisciplinary collaborations could uncover unforeseen uses in areas such as nanotechnology or sustainable agriculture. As our understanding of molecular interactions deepens, compounds like 903551-23-5 will continue to play a pivotal role in advancing scientific knowledge and technological innovation.

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