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CS-W001157 4
Total: USD 88.00

(4-Bromophenoxy)trimethylsilane

  • CAS No. 17878-44-3

  • Cat. No. CS-0324138
  • Molecule weight245.19
  • Purity≥95%
  • MDL No.None

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

(4-Bromophenoxy)trimethylsilane|CS-0324138

Structure of 17878-44-3

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General Information

  • CAS No. 17878-44-3
  • Cat. No. CS-0324138
  • Purity ≥95%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₃BrOSi
  • Molecular Weight 245.19
  • Synonym(s) Silane, (4-bromophenoxy)trimethyl-
  • SMILES C[Si](C)(C)OC1=CC=C(C=C1)Br

Description

(4-Bromophenoxy)trimethylsilane features a brominated phenoxy group tethered to a trimethylsilyl moiety, enabling robust protection and selective functionalization. This bench-stable reagent facilitates efficient silicon-directed ortho-activation in cross-coupling reactions and serves as a key intermediate in the synthesis of silyl-protected aryl building blocks for pharmaceutical and materials applications.

Application

(4-Bromophenoxy)trimethylsilane serves as a stable, bench-ready silyl ether protecting group for phenols, enabling selective deprotection under mild conditions. It facilitates efficient Suzuki-Miyaura and Stille coupling reactions through the pendant bromoaryl functionality, offering orthogonal reactivity in complex molecule synthesis. The trimethylsilyl group provides excellent stability during standard organic transformations while allowing straightforward removal with fluoride sources.

Synthesis

  • Route1
    • null|null
      1450-14-2
    • null|null
      106-41-2
    • ~%
    • In-stock
      (4-Bromophenoxy)trimethylsilane|CS-0324138
      17878-44-3

    References

    • Journal of Organic Chemistry, , vol. 38, # 1 p. 6 - 11
  • Route2
    • null|null
      75-79-6
    • null|null
      106-41-2
    • ~%
    • In-stock
      (4-Bromophenoxy)trimethylsilane|CS-0324138
      17878-44-3

    References

    • US2611778 , ; C. A., , p. 11244
  • Route3
    • null|null
      106-41-2
    • null|null
      999-97-3
    • ~97%
    • In-stock
      (4-Bromophenoxy)trimethylsilane|CS-0324138
      17878-44-3

    References

    • Russian Journal of General Chemistry, , vol. 70, # 11 p. 1749 - 1751

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   9.23
  • LogP   3.6628
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   2

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