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CS-W001157 4
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3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(1-methylethyl)silyl]-1H-pyrrole

  • CAS No. 365564-11-0

  • Cat. No. CS-0051659
  • Purity≥97%
  • MDL No.None

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

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(1-methylethyl)silyl]-1H-pyrrole|CS-0051659

Structure of 365564-11-0

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General Information

  • CAS No. 365564-11-0
  • Cat. No. CS-0051659
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₉H₃₆BNO₂Si
  • Molecular Weight 349.39
  • Synonym(s) N-TIPS pyrrole-3-boronic acid pinacol ester
  • SMILES CC(C)[Si](C(C)C)(C(C)C)N1C=CC(=C1)B1OC(C)(C)C(C)(C)O1

Description

This pyrrole derivative features a boronate ester group paired with a sterically shielded tris(1-methylethyl)silyl protecting group, enabling stable, selective coupling in Suzuki-Miyaura reactions. The tetramethylcyclopentadienylboronate moiety facilitates efficient cross-coupling under mild conditions, while the bulky silyl group prevents undesired side reactions and enhances shelf life.

Synthesis

  • Route1
    • In-stock
      3-Bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrole|CS-0038939
      87630-36-2
    • null|null
      25015-63-8
    • ~83%
    • In-stock
      3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(1-methylethyl)silyl]-1H-pyrrole|CS-0051659
      365564-11-0

    References

    • Billingsley, Kelvin; Buchwald, Stephen L. Journal of the American Chemical Society, 2007 , vol. 129, # 11 p. 3358 - 3366
  • Route2

    References

    • THE UNIVERSITY OF MANCHESTER; INGLESON, Michael James Patent: WO2012/25760 A1, 2012 ; Location in patent: Page/Page column 57 ;
  • Route3

    References

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

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   23.39
  • LogP   4.8109
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   5

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