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2-Hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

  • CAS No. 620595-36-0

  • Cat. No. CS-0088575
  • Molecule weight248.08
  • Purity≥97%
  • MDL No.MFCD11846347

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

2-Hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde|CS-0088575

Structure of 620595-36-0

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General Information

  • CAS No. 620595-36-0
  • Cat. No. CS-0088575
  • Purity ≥97%
  • MDL No. MFCD11846347
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₇BO₄
  • Molecular Weight 248.08
  • Synonym(s) 2-Hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzaldehyde
  • SMILES CC(O1)(C)C(C)(C)OB1C2=CC(C=O)=C(O)C=C2

Description

This boronate-functional aldehyde integrates seamlessly into Suzuki-Miyaura coupling workflows, offering reliable stability under standard conditions. The ortho-hydroxyl group enables chelation in transition-metal catalysis, while the tetramethyl-dioxaborolane moiety ensures efficient cross-coupling with aryl halides.

Application

2-Hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The ortho-hydroxyl and aldehyde groups enable chelation-assisted coupling and facilitate downstream functionalization. Its stability under ambient conditions and ease of purification make it well-suited for iterative synthesis of complex phenolic scaffolds and biaryl architectures in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • BIOENERGENIX; MCCALL, John M.; ROMERO, Donna L.; KELLY, Robert C. Patent: WO2012/119046 A2, 2012 ; Location in patent: Page/Page column 114 ;
  • Route2

    References

    • McKiernan, Gordon J.; Hartley, Richard C. Organic Letters, 2003 , vol. 5, # 23 p. 4389 - 4392
  • Route3

    References

    • McKiernan, Gordon J.; Hartley, Richard C. Organic Letters, 2003 , vol. 5, # 23 p. 4389 - 4392

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-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P501

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Computational Chemistry Data

  • TPSA   55.76
  • LogP   1.5039
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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