Cas no 875305-81-0 (5-chloro-1H-Indole-7-carboxylic acid)

5-Chloro-1H-indole-7-carboxylic acid is a versatile heterocyclic compound featuring both chloro and carboxylic acid functional groups on an indole scaffold. Its molecular structure makes it a valuable intermediate in organic synthesis, particularly in the development of pharmaceuticals and agrochemicals. The chloro substituent enhances reactivity for further functionalization, while the carboxylic acid group allows for derivatization into esters, amides, or other derivatives. This compound exhibits high purity and stability, making it suitable for research applications in medicinal chemistry and material science. Its well-defined structure and functional group compatibility contribute to its utility in constructing complex molecules, including biologically active indole-based compounds.
5-chloro-1H-Indole-7-carboxylic acid structure
875305-81-0 structure
Product Name:5-chloro-1H-Indole-7-carboxylic acid
CAS No:875305-81-0
MF:C9H6ClNO2
MW:195.602441310883
MDL:MFCD16037410
CID:1011923
PubChem ID:66868563
Update Time:2025-05-23

5-chloro-1H-Indole-7-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 5-chloro-1H-Indole-7-carboxylic acid
    • 1H-INDOLE-7-CARBOXYLIC ACID,5-CHLORO
    • 5-Chloro-7-indolecarboxylic acid
    • 5-chloro-1H-indole-7-carboxylicacid
    • SB15155
    • FT-0762034
    • EN300-1608559
    • SCHEMBL988532
    • CS-0050542
    • 5-chloro-1H-indol-7-carboxylic acid
    • A858195
    • AS-43119
    • 875305-81-0
    • MFCD16037410
    • AMY35042
    • NQDMTJYCOYPTOZ-UHFFFAOYSA-N
    • AKOS023770518
    • MDL: MFCD16037410
    • Inchi: 1S/C9H6ClNO2/c10-6-3-5-1-2-11-8(5)7(4-6)9(12)13/h1-4,11H,(H,12,13)
    • InChI Key: NQDMTJYCOYPTOZ-UHFFFAOYSA-N
    • SMILES: ClC1C=C(C(=O)O)C2=C(C=1)C=CN2

Computed Properties

  • Exact Mass: 195.0087061g/mol
  • Monoisotopic Mass: 195.0087061g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • 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: 2.2
  • Topological Polar Surface Area: 53.1?2

Experimental Properties

  • Density: 1.5±0.1 g/cm3
  • Boiling Point: 440.6±25.0 °C at 760 mmHg
  • Flash Point: 220.2±23.2 °C
  • Vapor Pressure: 0.0±1.1 mmHg at 25°C

5-chloro-1H-Indole-7-carboxylic acid Security Information

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Additional information on 5-chloro-1H-Indole-7-carboxylic acid

Introduction to 5-chloro-1H-Indole-7-carboxylic acid (CAS No. 875305-81-0)

5-chloro-1H-Indole-7-carboxylic acid, identified by the Chemical Abstracts Service Number (CAS No.) 875305-81-0, is a significant compound in the realm of pharmaceutical chemistry and medicinal research. This heterocyclic aromatic acid derivative has garnered considerable attention due to its versatile structural framework and potential biological activities. The presence of both a chloro substituent and a carboxylic acid group on the indole core imparts unique reactivity, making it a valuable intermediate in the synthesis of various pharmacologically active molecules.

The indole scaffold, a prominent motif in natural products and bioactive compounds, is well-documented for its role in modulating diverse biological pathways. Specifically, 5-chloro-1H-Indole-7-carboxylic acid has been explored for its potential in inhibiting certain enzymes and receptors involved in inflammatory responses, neurodegenerative diseases, and cancer progression. Recent studies have highlighted its significance as a precursor in the development of novel therapeutic agents targeting these conditions.

In the context of modern drug discovery, the compound’s structural features make it an attractive candidate for further derivatization. The chloro group at the 5-position of the indole ring enhances electrophilicity, facilitating nucleophilic substitution reactions that can lead to the introduction of diverse functional groups. Concurrently, the carboxylic acid moiety at the 7-position allows for amide or ester formation, broadening the scope of possible derivatives. These chemical attributes have positioned 5-chloro-1H-Indole-7-carboxylic acid as a key building block in medicinal chemistry.

Recent advancements in computational chemistry have further underscored the importance of this compound. Molecular modeling studies suggest that 5-chloro-1H-Indole-7-carboxylic acid can interact with specific protein targets through hydrogen bonding and hydrophobic interactions. Such insights have guided researchers in designing analogs with enhanced binding affinity and selectivity. For instance, modifications at the 3-position of the indole ring have been investigated to optimize pharmacokinetic properties while maintaining biological efficacy.

The compound’s relevance extends beyond academic research; it has been incorporated into several preclinical studies evaluating its role in modulating immune responses. Preliminary data indicate that derivatives of 5-chloro-1H-Indole-7-carboxylic acid may exhibit immunomodulatory effects by influencing cytokine production and cell signaling pathways. These findings are particularly intriguing given the growing interest in immunotherapy for cancer and autoimmune diseases.

From a synthetic perspective, 5-chloro-1H-Indole-7-carboxylic acid serves as a versatile intermediate in multi-step organic transformations. Its synthesis typically involves chlorination of indole derivatives followed by carboxylation at the 7-position. Advances in catalytic methods have enabled more efficient and environmentally friendly routes to this compound, aligning with green chemistry principles. Such improvements are crucial for scaling up production while minimizing waste.

The pharmaceutical industry has taken note of these developments, with several companies exploring derivatives of 5-chloro-1H-Indole-7-carboxylic acid for therapeutic applications. Early-phase clinical trials are underway to assess safety and efficacy profiles of novel compounds derived from this scaffold. The outcomes of these trials could pave the way for new treatments targeting neurological disorders, chronic inflammation, and metabolic diseases.

In conclusion, 5-chloro-1H-Indole-7-carboxylic acid (CAS No. 875305-81-0) represents a promising area of research with significant implications for drug development. Its unique structural features, combined with recent advances in synthetic methodologies and computational biology, position it as a cornerstone compound in medicinal chemistry. As further studies unravel its biological potential, it is likely to remain at the forefront of pharmaceutical innovation.

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