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Ethyl 3-methyl-1H-indole-2-carboxylate

  • CAS No. 26304-51-8

  • Cat. No. CS-0151842
  • Purity≥97%
  • MDL No.MFCD00225365

*For research and further manufacturing use only, not for direct human use.

Ethyl 3-methyl-1H-indole-2-carboxylate|CS-0151842

Structure of 26304-51-8

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General Information

  • CAS No. 26304-51-8
  • Cat. No. CS-0151842
  • Purity ≥97%
  • MDL No. MFCD00225365
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₃NO₂
  • Molecular Weight 203.24
  • Synonym(s) Ethyl3-MEthyl-2-Indolecarboxylate
  • SMILES CCOC(=O)C1=C(C)C2=CC=CC=C2N1

Description

Ethyl 3-methyl-1H-indole-2-carboxylate features a sterically hindered indole core with a strategically positioned ester group, enabling seamless integration into diverse synthetic sequences. This bench-stable derivative serves as a key scaffold for pharmaceutical intermediates and functional materials, offering enhanced solubility and compatibility in transition-metal-catalyzed couplings.

Application

Ethyl 3-methyl-1H-indole-2-carboxylate serves as a versatile building block for the synthesis of indole-based pharmaceuticals and agrochemicals. Its methyl group at the 3-position enhances regioselectivity in electrophilic substitution, while the ester functionality enables facile manipulation via hydrolysis, reduction, or coupling reactions. Bench-stable and readily purified by column chromatography, it functions effectively in standard synthetic workflows involving Pd-catalyzed cross-coupling, cyclization, and functional group interconversions.

Synthesis

  • Route1
    • null|null
      5439-83-8
    • ~84%
    • In-stock
      Ethyl 3-methyl-1H-indole-2-carboxylate|CS-0151842
      26304-51-8

    References

    • Wadia, M. S.; Mali, R. S.; Tilve, S. G.; Yadav, V. J. Synthesis, 1987 , # 4 p. 401 - 404
  • Route2
    • null|null
      2999-46-4
    • In-stock
      2'-Bromoacetophenone|CS-W007689
      2142-69-0
    • ~99%
    • In-stock
      Ethyl 3-methyl-1H-indole-2-carboxylate|CS-0151842
      26304-51-8

    References

    • Gu, Lijun; Li, Xiangguang Journal of the Brazilian Chemical Society, 2011 , vol. 22, # 11 p. 2036 - 2039
  • Route3
    • Ethyl 2-diazo-2-(diethoxyphosphoryl)acetate|CS-0771571
      17507-56-1
    • 2'-Aminoacetophenone Linagliptin Impurity|CS-0229112
      551-93-9
    • ~81%
    • In-stock
      Ethyl 3-methyl-1H-indole-2-carboxylate|CS-0151842
      26304-51-8

    References

    • Nakamura, Yoshinori; Ukita, Tatsuzo Organic Letters, 2002 , vol. 4, # 14 p. 2317 - 2320

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   42.09
  • LogP   2.65302
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   2

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