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CS-W001157 4
Total: USD 88.00

tert-Butyl 5-amino-1H-indole-1-carboxylate

  • CAS No. 166104-20-7

  • Cat. No. CS-W018798
  • Purity≥97%
  • MDL No.MFCD04114746

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

tert-Butyl 5-amino-1H-indole-1-carboxylate|CS-W018798

Structure of 166104-20-7

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General Information

  • CAS No. 166104-20-7
  • Cat. No. CS-W018798
  • Purity ≥97%
  • MDL No. MFCD04114746
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₆N₂O₂
  • Molecular Weight 232.28
  • Synonym(s) 1-Boc-5-Aminoindole
  • SMILES O=C(N1C=CC2=C1C=CC(N)=C2)OC(C)(C)C

Description

tert-Butyl 5-amino-1H-indole-1-carboxylate delivers a bench-stable, moisture-tolerant scaffold for indole-based drug discovery. This protected amine integrates seamlessly into synthetic routes requiring selective functionalization at the 5-position. The tert-butyl ester facilitates purification and downstream deprotection under mild acidic conditions.

Application

tert-Butyl 5-amino-1H-indole-1-carboxylate serves as a versatile building block for indole-based scaffolds, enabling direct functionalization at the C5 position via amine-directed transformations. The tert-butyl carbamate group provides excellent bench stability and facilitates straightforward deprotection under mild acidic conditions. Its compatibility with standard coupling reactions and tolerance to diverse functional groups make it well-suited for medicinal chemistry campaigns targeting kinase inhibitors and CNS-active compounds.

Synthesis

  • Route1

    References

    • Iyer, Pravin; Lucas, Matthew C.; Schoenfeld, Ryan Craig; Weikert, Robert James Patent: US2009/247568 A1, 2009 ; Location in patent: Page/Page column 36 ; US 20090247568 A1
  • Route2

    References

    • Journal of Medicinal Chemistry, , vol. 54, # 4 p. 1106 - 1110
  • Route3

    References

    • Journal of Medicinal Chemistry, , vol. 54, # 4 p. 1106 - 1110

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   57.25
  • LogP   3.0067
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   0

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