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CS-W001157 4
Total: USD 88.00

(4-(Benzyloxy)-2,6-dimethylphenyl)boronic acid

  • CAS No. 865139-18-0

  • Cat. No. CS-0068957
  • Purity≥97%
  • MDL No.None

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

(4-(Benzyloxy)-2,6-dimethylphenyl)boronic acid|CS-0068957

Structure of 865139-18-0

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General Information

  • CAS No. 865139-18-0
  • Cat. No. CS-0068957
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₁₇BO₃
  • Molecular Weight 256.10
  • Synonym(s) 4-(benzyloxy)-2,6-dimethylphenylboronic acid
  • SMILES OB(C1=C(C)C=C(OCC2=CC=CC=C2)C=C1C)O

Description

This boronic acid features a benzyloxy-substituted aryl core with methyl groups at the 2- and 6-positions, delivering enhanced stability and solubility in organic media. The pendant boronate moiety enables efficient Suzuki-Miyaura cross-coupling reactions under mild conditions, facilitating rapid assembly of complex biaryl architectures in synthetic and medicinal chemistry workflows.

Application

(4-(Benzyloxy)-2,6-dimethylphenyl)boronic acid serves as a stable, bench-ready building block for Suzuki-Miyaura cross-coupling reactions. Its ortho-methyl groups enhance regiochemical control and improve oxidative stability, while the benzyloxy substituent provides orthogonal protection and facilitates downstream functionalization. The boronic acid moiety enables efficient C–C bond formation with aryl halides and triflates under mild conditions, making it valuable for constructing complex biaryl scaffolds in medicinal chemistry and materials synthesis.

Synthesis

  • Route1
    • 5-(Benzyloxy)-2-bromo-1,3-dimethylbenzene|CS-0068956
      95741-44-9
    • ~60%
    • In-stock
      (4-(Benzyloxy)-2,6-dimethylphenyl)boronic acid|CS-0068957
      865139-18-0

    References

    • Takeda Pharmaceutical Company Limited Patent: EP1726580 A1, 2006 ; Location in patent: Page/Page column 117 ; EP 1726580 A1
  • Route2
    • null|null
      100-39-0
    • ~%
    • In-stock
      (4-(Benzyloxy)-2,6-dimethylphenyl)boronic acid|CS-0068957
      865139-18-0

    References

    • BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger Patent: WO2013/144098 A1, 2013 ;
  • Route3

    References

    • BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger Patent: WO2013/144098 A1, 2013 ;

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   49.69
  • LogP   1.56224
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   4

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