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2-(5-Bromothiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

  • CAS No. 676501-84-1

  • Cat. No. CS-0153866
  • Purity≥96%
  • MDL No.MFCD08063136

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

2-(5-Bromothiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0153866

Structure of 676501-84-1

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General Information

  • CAS No. 676501-84-1
  • Cat. No. CS-0153866
  • Purity ≥96%
  • MDL No. MFCD08063136
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₄BBrO₂S
  • Molecular Weight 289.00
  • Synonym(s) 5-bromothiophene-2-boronic acid pinacol ester
  • SMILES CC1(C)C(C)(C)OB(C2=CC=C(Br)S2)O1

Description

This boronate ester features a bromothiophene moiety paired with a tetramethyl-substituted dioxaborolane ring, delivering high stability and compatibility in cross-coupling reactions. The electron-rich thiophene unit enhances reactivity in palladium-catalyzed transformations, enabling efficient coupling under standard conditions.

Application

2-(5-Bromothiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron building block for palladium-catalyzed cross-coupling reactions. The bromo-thiophene moiety enables efficient Suzuki-Miyaura coupling with diverse aryl and heteroaryl partners, facilitating the construction of biologically relevant thiophene-containing scaffolds. Its tetramethyl-substituted dioxaborolane ring ensures excellent shelf stability, minimal protodeboronation, and compatibility with common functional groups, making it ideal for modular synthesis in medicinal chemistry and materials science applications.

Safety Information

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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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   18.46
  • LogP   2.8098
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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