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CS-W001157 4
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tert-Butyl 5-bromoisoindoline-2-carboxylate

  • CAS No. 201940-08-1

  • Cat. No. CS-W003696
  • Purity≥98%
  • MDL No.MFCD09953049

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

tert-Butyl 5-bromoisoindoline-2-carboxylate|CS-W003696

Structure of 201940-08-1

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General Information

  • CAS No. 201940-08-1
  • Cat. No. CS-W003696
  • Purity ≥98%
  • MDL No. MFCD09953049
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₆BrNO₂
  • Molecular Weight 298.18
  • Synonym(s) Tert-butyl 5-bromo-1,3-dihydro-2H-isoindole-2- carboxylate
  • SMILES CC(C)(OC(N1CC2=CC=C(Br)C=C2C1)=O)C

Description

tert-Butyl 5-bromoisoindoline-2-carboxylate features a brominated isoindoline core with a tert-butyl ester handle, enabling direct incorporation into diverse synthetic sequences. The electron-deficient bromo substituent facilitates transition-metal-catalyzed cross-coupling reactions, while the bench-stable ester group simplifies purification and downstream manipulation under standard conditions.

Application

tert-Butyl 5-bromoisoindoline-2-carboxylate serves as a versatile building block for the synthesis of isoindoline-based scaffolds prevalent in pharmaceuticals and functional materials. The bromine at the 5-position enables palladium-catalyzed cross-coupling reactions, while the tert-butyl ester group offers stability and facile deprotection under mild acidic conditions. Its compatibility with diverse reaction conditions supports efficient access to complex heterocyclic architectures in medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • Journal of Organic Chemistry, , vol. 77, # 24 p. 11296 - 11301
  • Route2

    References

    • Journal of Medicinal Chemistry, , vol. 50, # 2 p. 199 - 210

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-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   29.54
  • LogP   3.6998
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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