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Ethyl 6-bromoindole-2-carboxylate

  • CAS No. 103858-53-3

  • Cat. No. CS-W005383
  • Purity≥97%
  • MDL No.MFCD03094942

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

Ethyl 6-bromoindole-2-carboxylate|CS-W005383

Structure of 103858-53-3

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General Information

  • CAS No. 103858-53-3
  • Cat. No. CS-W005383
  • Purity ≥97%
  • MDL No. MFCD03094942
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₀BrNO₂
  • Molecular Weight 268.11
  • Synonym(s) ethyl 6-bromo-1H-indole-2-carboxylate
  • SMILES BrC1=CC=C2C(=C1)[NH]C(=C2)C(=O)OCC

Description

Ethyl 6-bromoindole-2-carboxylate features a bromine substituent at the 6-position of the indole core, enhancing reactivity for cross-coupling transformations. The ester functionality enables direct use in Suzuki-Miyaura and Stille reactions, while maintaining bench-stable handling under standard conditions. This compound serves as a key building block in the synthesis of functionalized heterocycles and biologically active molecules.

Application

Ethyl 6-bromoindole-2-carboxylate serves as a versatile building block for the synthesis of substituted indoles and heterocyclic scaffolds. The bromo group enables palladium-catalyzed cross-coupling reactions, while the ester functionality supports selective transformations and derivatization. Its bench-stable nature and compatibility with standard synthetic protocols make it well-suited for medicinal chemistry and process development workflows.

Synthesis

  • Route1
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    • ~%
    • In-stock
      Ethyl 6-bromoindole-2-carboxylate|CS-W005383
      103858-53-3

    References

    • US6627651 B1, ;
  • Route2

    References

    • Sudhakara; Jayadevappa; Mahadevan; Hulikal, Vijaykumar Synthetic Communications, 2009 , vol. 39, # 14 p. 2506 - 2515
  • Route3

    References

    • US2002/68756 A1, ; US 20020068756 A1

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

Quality Control

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Computational Chemistry Data

  • TPSA   42.09
  • LogP   3.1071
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   2

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