Cas no 23967-44-4 (4-Chloro-1-methyl-1H-indole-2-carboxylic acid)

4-Chloro-1-methyl-1H-indole-2-carboxylic acid is a halogenated indole derivative with significant utility in organic synthesis and pharmaceutical research. Its structure features a chloro substituent at the 4-position and a methyl group at the 1-position, enhancing its reactivity and stability for further functionalization. The carboxylic acid moiety allows for versatile derivatization, making it a valuable intermediate in the development of bioactive compounds. This compound is particularly useful in medicinal chemistry for the synthesis of indole-based scaffolds, which are prevalent in drug discovery. Its well-defined chemical properties and high purity ensure consistent performance in synthetic applications.
4-Chloro-1-methyl-1H-indole-2-carboxylic acid structure
23967-44-4 structure
Product Name:4-Chloro-1-methyl-1H-indole-2-carboxylic acid
CAS No:23967-44-4
MF:C10H8ClNO2
MW:209.629021644592
MDL:MFCD07364732
CID:1070989
PubChem ID:4777909
Update Time:2025-05-19

4-Chloro-1-methyl-1H-indole-2-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 4-Chloro-1-methyl-1H-indole-2-carboxylic acid
    • 1H-indole-2-carboxylic acid, 4-chloro-1-methyl-
    • 4-chloro-1-methyl-1H-indole-2-carboxylic acid(SALTDATA: FREE)
    • MFCD07364732
    • AKOS004119369
    • VS-03366
    • SCHEMBL19343561
    • BBL012514
    • E81695
    • DTXSID30406470
    • 23967-44-4
    • ALBB-005038
    • STK501556
    • 4-Chloro-1-methyl-1H-indole-2-carboxylic acid, AldrichCPR
    • CS-0136788
    • 4-chloro-1-methylindole-2-carboxylic acid
    • MDL: MFCD07364732
    • Inchi: 1S/C10H8ClNO2/c1-12-8-4-2-3-7(11)6(8)5-9(12)10(13)14/h2-5H,1H3,(H,13,14)
    • InChI Key: VGCZPBOQBLXWRG-UHFFFAOYSA-N
    • SMILES: ClC1=CC=CC2=C1C=C(C(=O)O)N2C

Computed Properties

  • Exact Mass: 209.02444
  • Monoisotopic Mass: 209.0243562g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 1
  • Complexity: 246
  • 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: 42.2?2

Experimental Properties

  • PSA: 42.23

4-Chloro-1-methyl-1H-indole-2-carboxylic acid Security Information

4-Chloro-1-methyl-1H-indole-2-carboxylic acid Pricemore >>

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4-Chloro-1-methyl-1H-indole-2-carboxylic acid Related Literature

Additional information on 4-Chloro-1-methyl-1H-indole-2-carboxylic acid

Recent Advances in the Application of 4-Chloro-1-methyl-1H-indole-2-carboxylic acid (CAS: 23967-44-4) in Chemical Biology and Pharmaceutical Research

The compound 4-Chloro-1-methyl-1H-indole-2-carboxylic acid (CAS: 23967-44-4) has recently emerged as a key scaffold in medicinal chemistry and drug discovery. This indole derivative has attracted significant attention due to its versatile pharmacological properties and its role as a building block for more complex bioactive molecules. Recent studies have explored its potential in various therapeutic areas, including anti-inflammatory, anticancer, and antimicrobial applications.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the compound's effectiveness as a precursor for novel kinase inhibitors. Researchers utilized 4-Chloro-1-methyl-1H-indole-2-carboxylic acid to develop a series of potent and selective inhibitors targeting specific tyrosine kinases involved in cancer progression. The study highlighted the compound's optimal molecular geometry for binding to the ATP pocket of these kinases, with modifications at the carboxylic acid position yielding derivatives with improved pharmacokinetic properties.

In the field of anti-infective research, a team at the University of Cambridge reported in Bioorganic & Medicinal Chemistry Letters (2024) on the antimicrobial activity of 4-Chloro-1-methyl-1H-indole-2-carboxylic acid derivatives. The study found that certain halogenated analogs exhibited remarkable activity against drug-resistant bacterial strains, particularly MRSA and ESBL-producing E. coli. The presence of the chloro group at the 4-position was identified as crucial for maintaining antibacterial potency while reducing cytotoxicity against mammalian cells.

The compound's role in neurodegenerative disease research has also been explored. A recent Nature Communications paper (2024) described its incorporation into small molecules targeting α-synuclein aggregation in Parkinson's disease. The indole core provided optimal π-stacking interactions with amyloid fibrils, while the carboxylic acid moiety enabled salt bridge formation with key lysine residues. This dual interaction mechanism showed promise in preventing protein misfolding without disrupting normal α-synuclein function.

From a synthetic chemistry perspective, advances in the production of 4-Chloro-1-methyl-1H-indole-2-carboxylic acid have been significant. A 2024 Organic Process Research & Development publication detailed an improved, greener synthesis route using continuous flow chemistry, achieving higher yields (82%) and reduced environmental impact compared to traditional batch methods. This development is particularly important as demand for the compound increases in pharmaceutical manufacturing.

Looking forward, the unique structural features of 4-Chloro-1-methyl-1H-indole-2-carboxylic acid continue to inspire novel drug design strategies. Its balanced lipophilicity, molecular rigidity, and multiple sites for derivatization make it an attractive starting point for fragment-based drug discovery. Several pharmaceutical companies have included derivatives of this compound in their preclinical pipelines, particularly for oncology and CNS disorders, suggesting its importance will likely grow in coming years.

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