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tert-Butyl 6-formyl-1H-indole-1-carboxylate

  • CAS No. 127956-28-9

  • Cat. No. CS-0055865
  • Purity≥97%
  • MDL No.None

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

tert-Butyl 6-formyl-1H-indole-1-carboxylate|CS-0055865

Structure of 127956-28-9

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General Information

  • CAS No. 127956-28-9
  • Cat. No. CS-0055865
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₅NO₃
  • Molecular Weight 245.27
  • Synonym(s) tert-butyl 6-formylindole-1-carboxylate
  • SMILES O=C(N1C=CC2=C1C=C(C=O)C=C2)OC(C)(C)C

Description

tert-Butyl 6-formyl-1H-indole-1-carboxylate features a formyl group at the 6-position of the indole core, enabling direct functionalization in synthetic sequences. The tert-butyl ester provides stability and ease of manipulation under standard conditions, while the electron-deficient aldehyde facilitates conjugate additions and condensation reactions. This scaffold integrates readily into complex heterocyclic architectures.

Application

tert-Butyl 6-formyl-1H-indole-1-carboxylate serves as a versatile building block for indole-based scaffold synthesis, enabling direct functionalization at the C6 position via formyl group reactivity. Its bench-stable tert-butyl ester and electron-deficient formyl moiety offer excellent compatibility with nucleophilic additions, reductive aminations, and transition-metal-catalyzed coupling reactions. The molecule facilitates efficient access to substituted indoles and heterocyclic frameworks relevant to medicinal chemistry and process development.

Synthesis

  • Route1

    References

    • Carlier, Paul R.; Lam, Polo C.-H.; Wong, Dawn M. Journal of Organic Chemistry, 2002 , vol. 67, # 17 p. 6256 - 6259
  • Route2

    References

    • Woolridge, Elisa M.; Rokita, Steven E. Tetrahedron Letters, 1989 , vol. 30, # 45 p. 6117 - 6120
  • Route3

    References

    • Woolridge, Elisa M.; Rokita, Steven E. Tetrahedron Letters, 1989 , vol. 30, # 45 p. 6117 - 6120

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-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P501

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Computational Chemistry Data

  • TPSA   48.3
  • LogP   3.237
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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