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CS-W001157 4
Total: USD 88.00

3-Bromophenylboronic acid pinacol ester

  • CAS No. 594823-67-3

  • Cat. No. CS-W000950
  • Molecule weight282.97
  • Purity≥97%
  • MDL No.MFCD12545926

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

3-Bromophenylboronic acid pinacol ester|CS-W000950

Structure of 594823-67-3

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General Information

  • CAS No. 594823-67-3
  • Cat. No. CS-W000950
  • Purity ≥97%
  • MDL No. MFCD12545926
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₆BBrO₂
  • Molecular Weight 282.97
  • Synonym(s) 3-Bromophenylboronic Acid Pinacol Ester
  • SMILES Brc1cccc(c1)B1OC(C(O1)(C)C)(C)C

Description

This boronate ester features a brominated phenyl moiety integrated with a tetramethyl-substituted dioxaborolane ring, enabling efficient Suzuki-Miyaura cross-coupling under standard conditions. The sterically shielded boronate group enhances stability and minimizes protodeboronation, while the ortho-bromine facilitates sequential functionalization.

Application

2-(3-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. The 3-bromophenyl group enables efficient coupling with aryl and heteroaryl halides under standard catalytic conditions. Its tetramethyl-substituted dioxaborolane core offers enhanced stability, minimal protodeboronation, and straightforward purification, making it ideal for constructing biaryl scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Jiang, Qin; Ryan, Meagan; Zhichkin, Paul Journal of Organic Chemistry, 2007 , vol. 72, # 17 p. 6618 - 6620
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      3-Bromophenylboronic acid pinacol ester|CS-W000950
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    References

    • Labre, Flavien; Gimbert, Yves; Bannwarth, Pierre; Olivero, Sandra; Dunach, Elisabet; Chavant, Pierre Y. Organic Letters, 2014 , vol. 16, # 9 p. 2366 - 2369
  • Route3
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      3-Bromophenylboronic acid pinacol ester|CS-W000950
      594823-67-3

    References

    • Zhu, Chuan; Yamane, Motoki Organic Letters, 2012 , vol. 14, # 17 p. 4560 - 4563

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

Quality Control

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Computational Chemistry Data

  • TPSA   18.46
  • LogP   2.7483
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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