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CS-W001157 4
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Ethyl 7-bromo-1H-indole-2-carboxylate

  • CAS No. 16732-69-7

  • Cat. No. CS-W004711
  • Purity≥96%
  • MDL No.MFCD04972046

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

Ethyl 7-bromo-1H-indole-2-carboxylate|CS-W004711

Structure of 16732-69-7

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General Information

  • CAS No. 16732-69-7
  • Cat. No. CS-W004711
  • Purity ≥96%
  • MDL No. MFCD04972046
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₀BrNO₂
  • Molecular Weight 268.11
  • Synonym(s) ETHYL 7-BROMOINDOLE-2-CARBOXYLATE; Ethyl 7-bromo-1H-indole-2-carboxylate
  • SMILES O=C(C(N1)=CC2=C1C(Br)=CC=C2)OCC

Description

Ethyl 7-bromo-1H-indole-2-carboxylate features a brominated indole core with a strategically positioned ester group, enabling direct functionalization in cross-coupling reactions. The electron-deficient indole ring enhances reactivity in palladium-catalyzed transformations, while the bench-stable ethyl ester facilitates handling and purification under standard conditions. This compound serves as a key intermediate for synthesizing biologically active indole derivatives.

Application

Ethyl 7-bromo-1H-indole-2-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling direct functionalization at the C7 position via palladium-catalyzed cross-coupling reactions. The bromo group exhibits high reactivity in Suzuki, Stille, and Negishi transformations, while the indole core supports electrophilic substitution at C3 and compatibility with standard protecting group strategies. Bench-stable and readily purified by flash chromatography, it facilitates efficient access to substituted indole scaffolds relevant to medicinal chemistry and materials science.

Synthesis

  • Route1

    References

    • Poriel, Cyril; Lachia, Mathilde; Wilson, Claire; Davies, James R.; Moody, Christopher J. Journal of Organic Chemistry, 2007 , vol. 72, # 8 p. 2978 - 2987
  • Route2

    References

    • US2011/269737 A1, ; US 20110269737 A1
  • Route3

    References

    • Journal of Medicinal Chemistry, , vol. 46, # 19 p. 3957 - 3960

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   3.1071
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   2

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