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Ethyl 2-(1H-indol-3-yl)acetate

  • CAS No. 778-82-5

  • Cat. No. CS-W015454
  • Purity≥98%
  • MDL No.MFCD00005635

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

Ethyl 2-(1H-indol-3-yl)acetate|CS-W015454

Structure of 778-82-5

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General Information

  • CAS No. 778-82-5
  • Cat. No. CS-W015454
  • Purity ≥98%
  • MDL No. MFCD00005635
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₃NO₂
  • Molecular Weight 203.24
  • Synonym(s) IAA Ethyl Ester
  • SMILES C1=CC=CC2=C1C(=C[NH]2)CC(OCC)=O

Description

Ethyl 2-(1H-indol-3-yl)acetate features a rigid indole core conjugated to an ester-functionalized side chain, enabling seamless integration into bioactive molecule scaffolds. This bench-stable, moisture-tolerant reagent facilitates efficient C–C bond formation and serves as a key intermediate in the synthesis of tryptophan analogs and heterocyclic pharmaceuticals.

Application

Ethyl 2-(1H-indol-3-yl)acetate serves as a versatile building block in medicinal chemistry, enabling efficient access to indole-based scaffolds through standard functional group transformations. Its bench-stable nature and compatibility with common coupling reactions facilitate straightforward derivatization for target molecule synthesis. The ester functionality supports further manipulation via hydrolysis, reduction, or cross-coupling protocols, making it a practical choice for constructing bioactive heterocycles and API intermediates.

Synthesis

  • Route1

    References

    • Chu, Chung K.; Suh, Jungjin; Cutler, Horace G. Journal of Heterocyclic Chemistry, 1986 , vol. 23, p. 1777 - 1779
  • Route2

    References

    • Kyowa Hakko Kogyo Co., Ltd. Patent: US5053408 A1, 1991 ;
  • Route3

    References

    • Heller, Stephen T.; Fu, Tingting; Sarpong, Richmond Organic Letters, 2012 , vol. 14, # 8 p. 1970 - 1973

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-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   42.09
  • LogP   2.2735
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   3

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