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tert-Butyl 3-(aminomethyl)-1H-indole-1-carboxylate

  • CAS No. 188988-46-7

  • Cat. No. CS-0094258
  • Purity≥96%
  • MDL No.MFCD06738803

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

tert-Butyl 3-(aminomethyl)-1H-indole-1-carboxylate|CS-0094258

Structure of 188988-46-7

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General Information

  • CAS No. 188988-46-7
  • Cat. No. CS-0094258
  • Purity ≥96%
  • MDL No. MFCD06738803
  • Storage -20°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₈N₂O₂
  • Molecular Weight 246.31
  • Synonym(s) tert-butyl 3-(aminomethyl)indole-1-carboxylate
  • SMILES O=C(N1C=C(CN)C2=C1C=CC=C2)OC(C)(C)C

Description

tert-Butyl 3-(aminomethyl)-1H-indole-1-carboxylate features a protected amine at the indole C3 position, enabling straightforward deprotection and functionalization. The tert-butyl ester group ensures stability during handling and purification, while the pendant aminomethyl moiety facilitates conjugation or further derivatization in medicinal chemistry campaigns.

Application

tert-Butyl 3-(aminomethyl)-1H-indole-1-carboxylate serves as a versatile building block for indole-based medicinal chemistry, enabling direct access to C3-functionalized indole scaffolds. The tert-butyl carbamate group provides excellent bench stability and ease of removal under mild acidic conditions, while the pendant primary amine facilitates downstream derivatization via amidation, alkylation, or reductive amination. Its compatibility with standard coupling protocols makes it ideal for constructing complex heterocyclic architectures in API development.

Synthesis

  • Route1

    References

    • Synlett, , vol. 1997, # 3 p. 289 - 290 Tetrahedron, , vol. 54, # 14 p. 3549 - 3566
  • Route2

    References

    • Tetrahedron, , vol. 54, # 14 p. 3549 - 3566
  • Route3

    References

    • Tetrahedron, , vol. 54, # 14 p. 3549 - 3566

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   57.25
  • LogP   2.8832
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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