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CS-W001157 4
Total: USD 88.00

(5-(Methoxycarbonyl)-2-methylphenyl)boronic acid

  • CAS No. 876189-18-3

  • Cat. No. CS-0042974
  • Purity≥95%
  • MDL No.MFCD11111429

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

(5-(Methoxycarbonyl)-2-methylphenyl)boronic acid|CS-0042974

Structure of 876189-18-3

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General Information

  • CAS No. 876189-18-3
  • Cat. No. CS-0042974
  • Purity ≥95%
  • MDL No. MFCD11111429
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₁BO₄
  • Molecular Weight None
  • Synonym(s) 5-Methoxycarbonyl-2-methylphenylboronic acid
  • SMILES OB(C1=CC(C(OC)=O)=CC=C1C)O

Description

This boronic acid features a methoxycarbonyl group at the 5-position and a methyl substituent at the 2-position, delivering enhanced solubility and stability under standard conditions. The para-directed electronic profile facilitates efficient Suzuki-Miyaura coupling reactions, enabling rapid construction of biaryl architectures in synthetic and medicinal chemistry workflows.

Application

(5-(Methoxycarbonyl)-2-methylphenyl)boronic acid serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, enabling efficient construction of biaryl scaffolds with retained ester functionality. Its bench-stable nature, compatibility with diverse reaction conditions, and tolerance for common functional groups facilitate straightforward synthesis of complex aromatic systems. The methyl and methoxycarbonyl substituents provide predictable electronic and steric modulation, enhancing utility in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Wang, Xiao-Jun; Sun, Xiufeng; Zhang, Li; Xu, Yibo; Krishnamurthy, Dhileepkumar; Senanayake, Chris H. Organic Letters, 2006 , vol. 8, # 2 p. 305 - 307
  • Route2
    • null|null
      67-56-1
    • In-stock
      3-Borono-4-methylbenzoic acid|CS-0043000
      170230-88-3
    • ~%
    • In-stock
      (5-(Methoxycarbonyl)-2-methylphenyl)boronic acid|CS-0042974
      876189-18-3

    References

    • Pal, Arnab; Berube, Marie; Hall, Dennis G. Angewandte Chemie - International Edition, 2010 , vol. 49, # 8 p. 1492 - 1495

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

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Computational Chemistry Data

  • TPSA   66.76
  • LogP   -0.53858
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   2

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