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CS-W001157 4
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3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

  • CAS No. 937366-54-6

  • Cat. No. CS-0137703
  • Purity≥95%
  • MDL No.MFCD09879158

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

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole|CS-0137703

Structure of 937366-54-6

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General Information

  • CAS No. 937366-54-6
  • Cat. No. CS-0137703
  • Purity ≥95%
  • MDL No. MFCD09879158
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₈BNO₂
  • Molecular Weight 243.11
  • Synonym(s) PINACOL ESTER INDOLE-5-BORONIC ACID
  • SMILES CC1(C)C(C)(C)OB(C2=CNC3=C2C=CC=C3)O1

Description

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole is a bench-stable boronate reagent featuring a planar indole core that enables efficient cross-coupling in palladium-catalyzed reactions. The tetramethyl-substituted dioxaborolane moiety enhances stability and solubility in polar organic solvents, facilitating reliable coupling with aryl and vinyl halides under standard conditions. This structure integrates seamlessly into complex molecular architectures, particularly in medicinal chemistry and materials synthesis.

Application

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The dioxaborolane group enables stable, room-temperature handling and facilitates efficient C–C bond formation with aryl and heteroaryl halides. Its compatibility with diverse functional groups and straightforward purification make it ideal for constructing biaryl scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Takagi, Jun; Sato, Kazuaki; Hartwig, John F; Ishiyama, Tatsuo; Miyaura, Norio Tetrahedron Letters, 2002 , vol. 43, # 32 p. 5649 - 5651
  • Route2

    References

    • Takagi, Jun; Sato, Kazuaki; Hartwig, John F; Ishiyama, Tatsuo; Miyaura, Norio Tetrahedron Letters, 2002 , vol. 43, # 32 p. 5649 - 5651
  • Route3

    References

    • Kallepalli, Venkata A.; Shi, Feng; Paul, Sulagna; Onyeozili, Edith N.; Maleczka Jr., Robert E.; Smith III, Milton R. Journal of Organic Chemistry, 2009 , vol. 74, # 23 p. 9199 - 9201

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

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Computational Chemistry Data

  • TPSA   34.25
  • LogP   2.4671
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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