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CS-W001157 4
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tert-Butyl 5-hydroxyindoline-1-carboxylate

  • CAS No. 170147-76-9

  • Cat. No. CS-0082129
  • Purity≥97%
  • MDL No.MFCD11045242

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

tert-Butyl 5-hydroxyindoline-1-carboxylate|CS-0082129

Structure of 170147-76-9

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General Information

  • CAS No. 170147-76-9
  • Cat. No. CS-0082129
  • Purity ≥97%
  • MDL No. MFCD11045242
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₇NO₃
  • Molecular Weight None
  • Synonym(s) N-Boc-5-Hydroxyindoline
  • SMILES O=C(N1CCC2=C1C=CC(O)=C2)OC(C)(C)C

Description

tert-Butyl 5-hydroxyindoline-1-carboxylate features a hydroxylated indoline core with a robust tert-butyl ester handle, enabling straightforward deprotection and functionalization. The molecule exhibits enhanced stability under standard bench conditions, facilitating its use in synthetic sequences requiring moisture-tolerant intermediates. This scaffold integrates readily into complex heterocyclic frameworks for medicinal chemistry applications.

Application

tert-Butyl 5-hydroxyindoline-1-carboxylate serves as a versatile scaffold for the synthesis of indoline-based pharmaceutical intermediates. The hydroxyl group enables selective derivatization via esterification, etherification, or oxidation to quinone methides, while the tert-butyl carbamate offers orthogonal protection for nitrogen during multi-step sequences. Its bench-stable nature and compatibility with standard coupling and reduction conditions facilitate efficient access to medicinally relevant heterocycles.

Synthesis

  • Route1
    • tert-Butyl 5-(benzyloxy)-1H-indole-1-carboxylate|CS-0154784
      170147-29-2
    • ~97%
    • In-stock
      tert-Butyl 5-hydroxyindoline-1-carboxylate|CS-0082129
      170147-76-9

    References

    • Igarashi; Inami; Hara; Koutoku; Oritani; Mase Chemical and Pharmaceutical Bulletin, 2000 , vol. 48, # 11 p. 1689 - 1697
  • Route2
    • null|null
      273408-46-1
    • ~89%
    • In-stock
      tert-Butyl 5-hydroxyindoline-1-carboxylate|CS-0082129
      170147-76-9

    References

    • Stark, Lucy M.; Lin, Xiao-Fa; Flippin, Lee A. Journal of Organic Chemistry, 2000 , vol. 65, # 10 p. 3227 - 3230
  • Route3
    • In-stock
      Di-tert-butyl dicarbonate|CS-0017817
      24424-99-5
    • Indolin-5-ol|CS-W007244
      172078-33-0
    • ~61%
    • In-stock
      tert-Butyl 5-hydroxyindoline-1-carboxylate|CS-0082129
      170147-76-9

    References

    • BIOGEN IDEC MA INC.; THOMAS, Jermaine; LIU, Xiaogao; LIN, Edward, Yin-Shiang; ZHENG, Guo, Zhu; MA, Bin; CALDWELL, Richard, D.; GUCKIAN, Kevin, M.; KUMARAVEL, Gnanasambandam; TAVERAS, Arthur, G. Patent: WO2011/17561 A1, 2011 ; Location in patent: Page/Page column 47 ; WO 2011/017561 A1

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   49.77
  • LogP   2.6898
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   0

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