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CS-W001157 4
Total: USD 88.00

5-Bromoindoline

  • CAS No. 22190-33-6

  • Cat. No. CS-M0075
  • Purity≥98%
  • MDL No.MFCD00027410

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

5-Bromoindoline|CS-M0075

Structure of 22190-33-6

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General Information

  • CAS No. 22190-33-6
  • Cat. No. CS-M0075
  • Purity ≥98%
  • MDL No. MFCD00027410
  • 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) 5-BROMO-2,3-DIHYDRO-1H-INDOLE
  • SMILES BrC1=CC=C(NCC2)C2=C1

Description

5-Bromoindoline features a bromine substituent at the 5-position of the indoline scaffold, enhancing its utility in transition-metal-catalyzed coupling reactions. This bench-stable heterocycle serves as a key intermediate in medicinal chemistry, where its electron-deficient character supports efficient functionalization.

Application

5-Bromoindoline serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions for the construction of biaryl and heteroaryl scaffolds. Its bromine substituent provides high reactivity in Suzuki, Stille, and Negishi couplings, while the indoline core offers favorable stability and solubility for bench-scale synthesis. The molecule functions as a key intermediate in the development of kinase inhibitors and other bioactive compounds.

Synthesis

  • Route1

    References

    • Johnson, Kirsten F.; Van Zeeland, Ryan; Stanley, Levi M. Organic Letters, 2013 , vol. 15, # 11 p. 2798 - 2801
  • Route2

    References

    • Sassatelli, Mathieu; Saab, Elias; Anizon, Fabrice; Prudhomme, Michelle; Moreau, Pascale Tetrahedron Letters, 2004 , vol. 45, # 25 p. 4827 - 4830
  • Route3
    • null|null
      918529-91-6
    • ~91%
    • In-stock
      5-Bromoindoline|CS-M0075
      22190-33-6

    References

    • Suarez-Castillo, Oscar R.; Beiza-Granados, Lidia; Melendez-Rodriguez, Myriam; Alvarez-Hernandez, Alejandro; Morales-Rios, Martha S.; Joseph-Nathan, Pedro Journal of Natural Products, 2006 , vol. 69, # 11 p. 1596 - 1600

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 : P261-P264-P271-P280-P302+P352-P304+P340-P362-P405-P501

Quality Control

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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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