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CS-W001157 4
Total: USD 88.00

3-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine

  • CAS No. 929203-04-3

  • Cat. No. CS-W021761
  • Molecule weight281.16
  • Purity≥97%
  • MDL No.None

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

3-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine|CS-W021761

Structure of 929203-04-3

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General Information

  • CAS No. 929203-04-3
  • Cat. No. CS-W021761
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₇H₂₀BNO₂
  • Molecular Weight 281.16
  • Synonym(s) 4-(3-Pyridinyl)phenylboronic acid pinacol ester
  • SMILES CC1(OB(C2=CC=C(C3=CC=CN=C3)C=C2)OC1(C)C)C

Description

3-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine is a boronate-functionalized heteroaryl building block featuring a pyridine core paired with a sterically shielded diborane moiety. This structure enables efficient Suzuki-Miyaura cross-coupling under standard conditions, delivering conjugated biaryls with high functional group tolerance and stability during storage and handling.

Application

3-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine serves as a versatile Suzuki-Miyaura coupling partner, enabling efficient construction of biaryl scaffolds under mild conditions. The boronate ester group exhibits excellent bench stability, tolerates diverse functional groups, and facilitates reliable cross-coupling with aryl halides and pseudohalides. Its pyridine moiety provides a rigid, polar framework suitable for medicinal chemistry applications and metal coordination in catalytic systems.

Synthesis

  • Route1
    • 3-(4-Chlorophenyl)pyridine|CS-0193271
      5957-97-1
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~89%
    • In-stock
      3-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine|CS-W021761
      929203-04-3

    References

    • Su, Shi-Jian; Tanaka, Daisaku; Li, Yan-Jun; Sasabe, Hisahiro; Takeda, Takashi; Kido, Junji Organic Letters, 2008 , vol. 10, # 5 p. 941 - 944
  • Route2

    References

    • Angewandte Chemie - International Edition, , vol. 52, # 44 p. 11581 - 11584 Angew. Chem., , vol. 125, # 44 p. 11795 - 11798
  • Route3

    References

    • Angewandte Chemie - International Edition, , vol. 52, # 44 p. 11581 - 11584 Angew. Chem., , vol. 125, # 44 p. 11795 - 11798

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   31.35
  • LogP   3.0478
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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