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3-Bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrole

  • CAS No. 87630-36-2

  • Cat. No. CS-0038939
  • Purity≥95%
  • MDL No.MFCD01321136

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

3-Bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrole|CS-0038939

Structure of 87630-36-2

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General Information

  • CAS No. 87630-36-2
  • Cat. No. CS-0038939
  • Purity ≥95%
  • MDL No. MFCD01321136
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₂₄BrNSi
  • Molecular Weight None
  • Synonym(s) Bromotriisopropylsilylpyrrole
  • SMILES CC(C)[Si](C(C)C)(C(C)C)N1C=CC(=C1)Br

Description

This tris(tert-butyl)silyl-protected pyrrole delivers enhanced stability and solubility in organic media, enabling reliable use in cross-coupling reactions. The bulky silyl group prevents undesired side reactions while the bromo substituent provides a reactive handle for palladium-catalyzed transformations.

Application

3-Bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrole serves as a stable, bench-ready building block for the synthesis of functionalized pyrroles. The tris(propan-2-yl)silyl group provides exceptional steric protection and enhances solubility, enabling efficient purification and compatibility with palladium-catalyzed cross-coupling reactions. Its bromine substituent facilitates diverse transformations including Suzuki-Miyaura, Stille, and Negishi couplings, making it a versatile scaffold for constructing complex heterocyclic architectures in medicinal chemistry and materials science.

Synthesis

  • Route1

    References

    • Stefan, Klaus-Peter; Schuhmann, Wolfgang; Parlar, Harun; Korte, Friedhelm Chemische Berichte, 1989 , vol. 122, p. 169 - 174
  • Route2
    • null|null
      13154-24-0
    • ~%
    • In-stock
      3-Bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrole|CS-0038939
      87630-36-2

    References

    • Angewandte Chemie - International Edition, , vol. 45, # 21 p. 3484 - 3488
  • Route3
    • In-stock
      1-(Triisopropylsilyl)-1H-pyrrole|CS-0132446
      87630-35-1
    • ~86%
    • In-stock
      3-Bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrole|CS-0038939
      87630-36-2
    • null|null
      130408-79-6

    References

    • Chemistry - A European Journal, , vol. 10, # 24 p. 6497 - 6509

Safety Information

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GHS Pictogram : N/A
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Hazard Statements : N/A
Precautionary Statements : N/A

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Computational Chemistry Data

  • TPSA   4.93
  • LogP   5.2742
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   4

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