Cas no 766557-02-2 (6-Chloro-1H-indole-3-carboxylic acid)

6-Chloro-1H-indole-3-carboxylic acid is a halogenated indole derivative widely used as a key intermediate in organic synthesis and pharmaceutical research. Its structural features, including the chloro substituent at the 6-position and the carboxylic acid group at the 3-position, make it a versatile building block for the development of biologically active compounds. This compound is particularly valuable in medicinal chemistry for the synthesis of indole-based scaffolds, which are prevalent in drug discovery. Its high purity and stability ensure reliable performance in coupling reactions, heterocycle formation, and other synthetic applications. The product is commonly employed in the preparation of agrochemicals, pharmaceuticals, and functional materials.
6-Chloro-1H-indole-3-carboxylic acid structure
766557-02-2 structure
Product Name:6-Chloro-1H-indole-3-carboxylic acid
CAS No:766557-02-2
MF:C9H6ClNO2
MW:195.602441310883
MDL:MFCD07776607
CID:550873
PubChem ID:18453235
Update Time:2025-06-15

6-Chloro-1H-indole-3-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 6-Chloroindole-3-carboxylic acid
    • 1H-INDOLE-3-CARBOXYLIC ACID,6-CHLORO
    • 1H-Indole-3-carboxylicacid, 6-chloro-
    • 6-Chloro-1H-indole-3-carboxylic acid
    • 1H-Indole-3-carboxylic acid, 6-chloro-
    • KSC375S0H
    • WHQHEMBHJZAHSB-UHFFFAOYSA-N
    • 6-Chloro-1H-indole-3-carboxylicacid
    • VI30325
    • RP25393
    • SY030199
    • BR-3
    • AMY32136
    • EN300-60290
    • J-518619
    • MFCD07776607
    • CS-W019457
    • 76655-02-2
    • FT-0648709
    • DTXSID70594007
    • AKOS005362540
    • A847114
    • Z385446076
    • SCHEMBL613332
    • 766557-02-2
    • FS-3067
    • DB-075164
    • DTXCID80544770
    • ALBB-035435
    • MDL: MFCD07776607
    • Inchi: 1S/C9H6ClNO2/c10-5-1-2-6-7(9(12)13)4-11-8(6)3-5/h1-4,11H,(H,12,13)
    • InChI Key: WHQHEMBHJZAHSB-UHFFFAOYSA-N
    • SMILES: ClC1C=CC2C(C(=O)O)=CNC=2C=1

Computed Properties

  • Exact Mass: 195.00900
  • Monoisotopic Mass: 195.009
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 222
  • 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: 2.6
  • Topological Polar Surface Area: 53.1

Experimental Properties

  • Density: 1.548
  • Boiling Point: 449.7°C at 760 mmHg
  • Flash Point: 225.8°C
  • Refractive Index: 1.728
  • PSA: 53.09000
  • LogP: 2.51950

6-Chloro-1H-indole-3-carboxylic acid Security Information

6-Chloro-1H-indole-3-carboxylic acid 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%

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6-Chloro-1H-indole-3-carboxylic acid Production Method

6-Chloro-1H-indole-3-carboxylic acid Related Literature

Additional information on 6-Chloro-1H-indole-3-carboxylic acid

Comprehensive Overview of 6-Chloro-1H-indole-3-carboxylic acid (CAS No. 766557-02-2): Properties, Applications, and Industry Insights

6-Chloro-1H-indole-3-carboxylic acid (CAS 766557-02-2) is a halogenated indole derivative with significant relevance in pharmaceutical and agrochemical research. This compound, characterized by its chloro-substituted indole core and carboxylic acid functional group, serves as a versatile building block in organic synthesis. Its molecular formula C9H6ClNO2 and molecular weight of 195.6 g/mol make it particularly valuable for designing bioactive molecules targeting enzyme inhibition and receptor modulation.

Recent trends in drug discovery highlight the growing demand for indole-based scaffolds, with researchers frequently searching for "6-Chloroindole derivatives" and "indole-3-carboxylic acid applications." The compound's structural features enable diverse modifications, addressing current industry challenges like selective kinase inhibitors and sustainable crop protection agents. Analytical techniques such as HPLC purity testing (typically >98%) and NMR spectral data (δ 7.2-7.8 ppm aromatic protons) are critical for quality control in commercial batches.

From a green chemistry perspective, synthetic routes to 766557-02-2 increasingly incorporate catalytic chlorination methods and solvent-free conditions, responding to environmental concerns. Patent analyses reveal its utility in developing anti-inflammatory APIs and LED materials, with particular interest in its fluorescence properties for bioimaging probes. Storage recommendations typically suggest 2-8°C under inert atmosphere to maintain stability.

The compound's structure-activity relationship (SAR) profile makes it valuable for medicinal chemistry optimization, especially in neurological disorder research. Computational studies using molecular docking simulations frequently employ this scaffold due to its balanced lipophilicity (LogP ~2.1) and hydrogen bonding capacity. These properties address frequent search queries about "blood-brain barrier permeable compounds" and "fragment-based drug design."

Industrial scale-up considerations for 6-Chloro-1H-indole-3-carboxylic acid production emphasize continuous flow chemistry approaches, with technical documents often referencing pilot plant yields exceeding 80%. Regulatory compliance aspects focus on proper REACH registration documentation and ICH stability guidelines. The compound's thermal behavior (decomposition >250°C) and pH-dependent solubility (pKa ~4.2) are frequently studied parameters for formulation scientists.

Emerging applications in material science explore its potential in organic semiconductors, leveraging the indole ring's electron-rich nature. Comparative studies with 5-fluoro and 7-bromo analogs provide valuable insights for researchers investigating "halogen effects in heterocycles." The compound's crystallographic data (monoclinic space group P21/c) assists in co-crystal engineering for improved bioavailability.

Quality assurance protocols for CAS 766557-02-2 typically require residual solvent analysis by GC, heavy metal screening, and chiral purity verification. These rigorous standards respond to pharmaceutical industry demands reflected in search terms like "GMP-compliant intermediates." Recent process innovations have reduced isomeric impurities to <0.5%, addressing a common pain point in contract manufacturing discussions.

From a market perspective, the compound aligns with growing interest in targeted cancer therapies and neuroprotective agents. Its structure-property relationships are frequently modeled using QSAR algorithms, making it a subject in "computational chemistry case studies." The metabolic stability of derivatives (microsomal t1/2 >60 min) positions it favorably for lead optimization programs.

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