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CS-W001157 4
Total: USD 88.00

4-Bromoindoline

  • CAS No. 86626-38-2

  • Cat. No. CS-W006183
  • Purity≥97%
  • MDL No.MFCD07371633

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

4-Bromoindoline|CS-W006183

Structure of 86626-38-2

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General Information

  • CAS No. 86626-38-2
  • Cat. No. CS-W006183
  • Purity ≥97%
  • MDL No. MFCD07371633
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₈BrN
  • Molecular Weight 198.06
  • Synonym(s) 4-Bromo-2,3-dihydro-1H-Indole
  • SMILES BrC1=CC=CC2=C1CCN2

Description

4-Bromoindoline is a bench-stable heterocyclic building block featuring a bromine substituent at the 4-position of the indoline core. This electron-deficient moiety enables direct functionalization in cross-coupling reactions and serves as a key intermediate in the synthesis of biologically active compounds, particularly within medicinal chemistry and materials science applications.

Application

4-Bromoindoline serves as a versatile building block in medicinal chemistry and heterocyclic synthesis, enabling direct functionalization at the C4 position. Its bromine substituent facilitates palladium-catalyzed cross-coupling reactions, including Suzuki, Stille, and Negishi couplings, with high efficiency and selectivity. The indoline core provides a rigid, nitrogen-containing scaffold compatible with diverse downstream transformations, including oxidation to indolinones and electrophilic substitution. Bench-stable and readily purified by recrystallization or chromatography, 4-bromoindoline functions as a key intermediate in the construction of bioactive molecules and pharmaceutical candidates.

Synthesis

  • Route1

    References

    • Chekler, Eugene L. Piatnitski; Unwalla, Rayomond; Khan, Taukeer A.; Tangirala, Raghuram S.; Johnson, Mark; St. Andre, Michael; Anderson, James T.; Kenney, Thomas; Chiparri, Sue; McNally, Chris; Kilbourne, Edward; Thompson, Catherine; Nagpal, Sunil; Weber, Gregory; Schelling, Scott; Owens, Jane; Morris, Carl A.; Powell, Dennis; Verhoest, Patrick R.; Gilbert, Adam M. Journal of Medicinal Chemistry, 2014 , vol. 57, # 6 p. 2462 - 2471
  • Route2

    References

    • Curis, Inc.; Bao, Rudi; Lai, Chengjung; Qian, Changgeng Patent: US2013/102595 A1, 2013 ; Location in patent: Paragraph 0564; 0565 ;
  • Route3

    References

    • Journal of Heterocyclic Chemistry, , vol. 20, p. 349 - 352

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

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Computational Chemistry Data

  • TPSA   12.03
  • LogP   2.4171
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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