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CS-W001157 4
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5-Bromoisoindoline

  • CAS No. 127168-84-7

  • Cat. No. CS-B0781
  • Purity≥96%
  • MDL No.MFCD08234718

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

5-Bromoisoindoline|CS-B0781

Structure of 127168-84-7

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General Information

  • CAS No. 127168-84-7
  • Cat. No. CS-B0781
  • Purity ≥96%
  • MDL No. MFCD08234718
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₈BrN
  • Molecular Weight 198.06
  • Synonym(s) 5-bromo-2,3-dihydro-1H-isoindole
  • SMILES BrC1=CC2=C(CNC2)C=C1

Description

5-Bromoisoindoline features a brominated isoindoline core with enhanced reactivity at the 5-position, enabling direct functionalization in cross-coupling and C–H activation processes. This bench-stable heterocycle integrates readily into complex molecular architectures, serving as a key building block for pharmaceutical intermediates and functional materials.

Application

5-Bromoisoindoline serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions to access biologically relevant isoindoline derivatives. Its bromine substituent provides high reactivity in standard Suzuki, Stille, and Negishi couplings, while the core scaffold exhibits favorable bench stability and compatibility with common functional groups. This compound facilitates efficient construction of complex heterocyclic architectures found in pharmaceutical leads.

Synthesis

  • Route1

    References

    • Patel, Bhavesh H.; Barrett, Anthony G. M. Journal of Organic Chemistry, 2012 , vol. 77, # 24 p. 11296 - 11301
  • Route2

    References

    • ASTRAZENECA AB Patent: WO2004/60882 A1, 2004 ; Location in patent: Page 41 ; WO 2004/060882 A1
  • Route3

    References

    • Deng, Jianghe; Kerns, Jeffrey K.; Jin, Qi; Lin, Guoliang; Lin, Xichen; Lindenmuth, Michael; Neipp, Christopher; Nie, Hong; Thomas, Sonia M.; Widdowson, Katherine L. Patent: US2009/143372 A1, 2009 ; US 20090143372 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 : 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

Quality Control

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Computational Chemistry Data

  • TPSA   12.03
  • LogP   2.0523
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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