Cas no 128781-07-7 (5,6,7-Trimethoxy-1H-indole-2-carboxylic acid)

5,6,7-Trimethoxy-1H-indole-2-carboxylic acid is a substituted indole derivative characterized by its trimethoxy functional groups at the 5, 6, and 7 positions and a carboxylic acid moiety at the 2-position. This compound serves as a versatile intermediate in organic synthesis, particularly in the development of pharmaceuticals and bioactive molecules. Its structural features, including the electron-rich aromatic system and reactive carboxyl group, make it valuable for further functionalization and derivatization. The trimethoxy substitution pattern enhances stability and influences electronic properties, which can be advantageous in medicinal chemistry applications. The compound is typically handled under controlled conditions due to its potential sensitivity. Analytical methods such as HPLC and NMR confirm its purity and structural integrity.
5,6,7-Trimethoxy-1H-indole-2-carboxylic acid structure
128781-07-7 structure
Product Name:5,6,7-Trimethoxy-1H-indole-2-carboxylic acid
CAS No:128781-07-7
MF:C12H13NO5
MW:251.235323667526
MDL:MFCD02664478
CID:897909
PubChem ID:821052
Update Time:2025-10-29

5,6,7-Trimethoxy-1H-indole-2-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 5,6,7-Trimethoxy-1H-indole-2-carboxylic acid
    • 5,6,7-Trimethoxy-1h-indole-2-carboxylic acid
    • 1H-Indole-2-carboxylic acid,5,6,7-trimethoxy
    • 4,5,6-trimethoxy-indole-2-carboxylic acid
    • 5,6,7-trimethoxy-1H-indol-2-carboxylic acid
    • 5,6,7-trimethoxyiindole-2-carboxylic acid
    • 5,6,7-trimethoxyindole-2-carboxylic acid
    • AKOS JY2082680
    • 1H-Indole-2-carboxylic acid, 5,6,7-trimethoxy-
    • MLS000067352
    • JZMUJQGIASARGH-UHFFFAOYSA-N
    • SMR000124840
    • ZERO/005664
    • Opera_ID_1223
    • AMTGC090
    • HMS2485M24
    • STK784028
    • BBL012795
    • SBB013569
    • SB14716
    • BAS 10142221
    • ST4125074
    • AQ-776/42801281
    • MFCD02664478
    • AKOS000505603
    • F11821
    • CHEMBL1346897
    • CS-0050730
    • Z119989544
    • EN300-15086
    • SY097134
    • SR-01000368635
    • DB-062656
    • AS-3102
    • 128781-07-7
    • DTXSID40356275
    • J-005624
    • SCHEMBL1771123
    • SR-01000368635-1
    • MDL: MFCD02664478
    • Inchi: 1S/C12H13NO5/c1-16-8-5-6-4-7(12(14)15)13-9(6)11(18-3)10(8)17-2/h4-5,13H,1-3H3,(H,14,15)
    • InChI Key: JZMUJQGIASARGH-UHFFFAOYSA-N
    • SMILES: O(C)C1=C(C(=CC2C=C(C(=O)O)NC=21)OC)OC

Computed Properties

  • Exact Mass: 251.07900
  • Monoisotopic Mass: 251.07937252g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 4
  • Complexity: 311
  • 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
  • Topological Polar Surface Area: 80.8
  • XLogP3: 1.8

Experimental Properties

  • Density: 1.3±0.1 g/cm3
  • Melting Point: 216-218 °C
  • Boiling Point: 473.6±40.0 °C at 760 mmHg
  • Flash Point: 240.2±27.3 °C
  • PSA: 80.78000
  • LogP: 1.89190
  • Vapor Pressure: 0.0±1.2 mmHg at 25°C

5,6,7-Trimethoxy-1H-indole-2-carboxylic acid Security Information

5,6,7-Trimethoxy-1H-indole-2-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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Additional information on 5,6,7-Trimethoxy-1H-indole-2-carboxylic acid

Introduction to 5,6,7-Trimethoxy-1H-indole-2-carboxylic acid (CAS No. 128781-07-7)

5,6,7-Trimethoxy-1H-indole-2-carboxylic acid, with the chemical formula C12H13O4, is a significant compound in the field of pharmaceutical chemistry and natural product research. This indole derivative has garnered attention due to its structural complexity and potential biological activities. The presence of multiple methoxy groups at the 5-, 6-, and 7-positions of the indole core enhances its reactivity and makes it a valuable scaffold for drug discovery.

The compound is classified as a heterocyclic aromatic carboxylic acid, which places it in a category of molecules known for their diverse pharmacological properties. Indole derivatives are widely studied for their roles in various biological processes, including neurotransmission, immune responses, and cancer cell proliferation. The specific substitution pattern of 5,6,7-Trimethoxy-1H-indole-2-carboxylic acid contributes to its unique chemical behavior and functional potential.

In recent years, there has been a growing interest in indole-based compounds due to their versatility in medicinal chemistry. Researchers have explored modifications at different positions of the indole ring to develop novel therapeutic agents. For instance, derivatives with methoxy substitutions have shown promise in inhibiting certain enzymes and receptors involved in inflammation and pain pathways. The 5,6,7-Trimethoxy-1H-indole-2-carboxylic acid structure serves as a foundation for synthesizing more complex molecules with enhanced pharmacological effects.

One of the most compelling aspects of 5,6,7-Trimethoxy-1H-indole-2-carboxylic acid is its role as a precursor in the synthesis of biologically active molecules. Its carboxylic acid group at the 2-position allows for further functionalization via esterification, amidation, or other transformations, enabling the creation of diverse pharmacophores. This flexibility has made it a favorite among synthetic chemists working on developing new drugs.

The compound has been studied in various preclinical models for its potential applications in treating neurological disorders. For example, indole derivatives have been investigated for their ability to modulate serotonin receptors, which are implicated in conditions such as depression and anxiety. The methoxy-substituted indoles are particularly interesting because they can exhibit higher binding affinities to these receptors compared to their unsubstituted counterparts.

Recent advances in computational chemistry have also contributed to the understanding of 5,6,7-Trimethoxy-1H-indole-2-carboxylic acid's properties. Molecular modeling studies have helped predict its interactions with biological targets, providing insights into how it might behave within living systems. These simulations have been instrumental in guiding experimental designs and optimizing synthetic routes.

In addition to its pharmaceutical applications, 5,6,7-Trimethoxy-1H-indole-2-carboxylic acid has found utility in material science. Its aromatic structure and functional groups make it a suitable candidate for developing organic semiconductors and liquid crystals. These materials are used in electronic devices such as OLEDs (organic light-emitting diodes) and displays due to their ability to conduct electricity while maintaining stability.

The synthesis of 5,6,7-Trimethoxy-1H-indole-2-carboxylic acid typically involves multi-step organic reactions starting from readily available precursors like tryptophan or indirubin derivatives. Advances in green chemistry have led to more sustainable synthetic methods that minimize waste and reduce energy consumption. These eco-friendly approaches align with the broader goal of making drug development more environmentally responsible.

The biological activity of 5,6,7-Trimethoxy-1H-indole-2-carboxylic acid has also been explored in the context of anti-cancer research. Studies have shown that certain indole derivatives can induce apoptosis (programmed cell death) in cancer cells by interfering with key signaling pathways. The methoxy groups on the indole ring appear to enhance this effect by improving solubility and membrane permeability.

Another area where this compound has shown promise is in antimicrobial applications. Research indicates that indole derivatives can inhibit the growth of bacteria and fungi by disrupting essential cellular processes. The structural features of 5,6,7-Trimethoxy-1H-indole-2-carboxylic acid, particularly its hydrophobicity and ability to interact with microbial cell membranes, contribute to its antimicrobial properties.

The industrial production of 5,6,7-Trimethoxy-1H-indole-2-carboxylic acid has been optimized for scalability while maintaining high purity standards. Manufacturers employ advanced purification techniques such as column chromatography and recrystallization to ensure that the final product meets stringent quality requirements. These processes are critical for ensuring consistency across batches and compatibility with downstream applications.

In conclusion,5,6,7-Trimethoxyindolinecarboxylate, as represented by CAS No. 12878107–07–7, represents a versatile molecule with broad applications across multiple scientific disciplines including pharmaceuticals, materials science,and biotechnology.. Its unique structural features make it an invaluable tool for researchers seeking new ways to address complex challenges.. As our understanding of its properties continues to grow,this compound is likely to play an even greater role in future discoveries..

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