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CS-W001157 4
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tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindoline-2-carboxylate

  • CAS No. 905273-91-8

  • Cat. No. CS-W023015
  • Purity≥95%
  • MDL No.MFCD11226842

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

tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindoline-2-carboxylate|CS-W023015

Structure of 905273-91-8

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General Information

  • CAS No. 905273-91-8
  • Cat. No. CS-W023015
  • Purity ≥95%
  • MDL No. MFCD11226842
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₉H₂₈BNO₄
  • Molecular Weight 345.24
  • Synonym(s) tert-Butyl5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-isoindole-2-carboxylate
  • SMILES O=C(N1CC2=C(C=C(B3OC(C)(C)C(C)(C)O3)C=C2)C1)OC(C)(C)C

Description

tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindoline-2-carboxylate integrates a boronate handle with a sterically protected isoindoline scaffold, enabling efficient Suzuki-Miyaura coupling under mild conditions. This bench-stable reagent facilitates rapid access to functionalized isoindoline architectures in late-stage diversification workflows.

Application

tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindoline-2-carboxylate serves as a stable, bench-ready boronate building block for palladium-catalyzed cross-coupling reactions. The isoindoline scaffold provides a rigid, electron-rich heterocyclic core useful in medicinal chemistry, while the diborane moiety enables efficient Suzuki-Miyaura coupling under mild conditions. Functional group tolerance and straightforward purification make it ideal for modular synthesis of complex scaffolds.

Synthesis

  • Route1

    References

    • Journal of Medicinal Chemistry, , vol. 50, # 2 p. 199 - 210
  • Route2

    References

    • Journal of Medicinal Chemistry, , vol. 50, # 2 p. 199 - 210
  • Route3

    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 : 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   48
  • LogP   3.2365
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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