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1H-Indole-1-carboxylic acid, 3-formyl-, 1,1-dimethylethyl ester

  • CAS No. 57476-50-3

  • Cat. No. CS-0031417
  • Purity≥97%
  • MDL No.MFCD00049230

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

1H-Indole-1-carboxylic acid, 3-formyl-, 1,1-dimethylethyl ester|CS-0031417

Structure of 57476-50-3

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General Information

  • CAS No. 57476-50-3
  • Cat. No. CS-0031417
  • Purity ≥97%
  • MDL No. MFCD00049230
  • 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 3-formyl-1H-indole-1-carboxylate
  • SMILES CC(C)(C)OC(N1C(C=CC=C2)=C2C(C=O)=C1)=O

Description

1-Boc-3-Formylindole delivers a protected indole scaffold with a reactive aldehyde handle, enabling direct conjugation in late-stage functionalization. The Boc group ensures stability during storage and handling, while the formyl moiety facilitates nucleophilic additions and oxime ligation under mild conditions. This reagent integrates seamlessly into synthetic sequences requiring site-specific modifications.

Application

1-Boc-3-Formylindole serves as a versatile building block in medicinal chemistry, enabling direct access to indole-based scaffolds through standard deprotection and functionalization protocols. The Boc group provides bench stability and facilitates selective manipulation of the indole nitrogen, while the formyl group offers a reactive handle for reductive amination, condensation, and heterocycle formation. Its compatibility with common coupling and protection strategies makes it well-suited for iterative synthesis of complex targets.

Synthesis

  • Route1

    References

    • Lee, Jong Seok; Shin, Junho; Lee, Hyi-Seung; Shin, Hee Jae; Lee, Yeon-Ju Bulletin of the Korean Chemical Society, 2013 , vol. 34, # 2 p. 357 - 358
  • Route2

    References

    • Kobayashi, Shu; Miyamura, Hiroyuki; Akiyama, Ryo; Ishida, Tasuku Journal of the American Chemical Society, 2005 , vol. 127, # 25 p. 9251 - 9254
  • Route3

    References

    • BARTOLOZZI, Alessandra; CHEN, Zhidong; DINES, Jonathon Alan; LO, Ho Yin; LOKE, Pui Leng; OLAGUE, Alan; RIETHER, Doris; TYE, Heather; WU, Lifen; ZINDELL, Renee M. Patent: US2013/196967 A1, 2013 ; Location in patent: Paragraph 0224; 0225 ;

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

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