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CS-W001157 4
Total: USD 88.00

4-Methyl-3-nitrophenylboronic acid

  • CAS No. 80500-27-2

  • Cat. No. CS-W000971
  • Purity≥97%
  • MDL No.MFCD00191550

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

4-Methyl-3-nitrophenylboronic acid|CS-W000971

Structure of 80500-27-2

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General Information

  • CAS No. 80500-27-2
  • Cat. No. CS-W000971
  • Purity ≥97%
  • MDL No. MFCD00191550
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₈BNO₄
  • Molecular Weight 180.95
  • Synonym(s) 3-Nitro-p-tolylboronic Acid (contains varying amounts of Anhydride)
  • SMILES OB(c1ccc(c(c1)[N+](=O)[O-])C)O

Description

4-Methyl-3-nitrophenylboronic acid features a boronate moiety flanked by electron-withdrawing nitro and electron-donating methyl groups, enabling efficient Suzuki-Miyaura coupling under standard conditions. This bench-stable reagent integrates seamlessly into complex molecule synthesis, offering predictable regiochemistry and enhanced solubility in polar organic solvents.

Application

4-Methyl-3-nitrophenylboronic acid serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, enabling the efficient construction of biaryl scaffolds. Its ortho-nitro and methyl substituents provide electronic modulation and steric control, enhancing regioselectivity in complex molecule assembly. The boronic acid functionality offers excellent bench stability and compatibility with diverse reaction conditions, facilitating straightforward purification and integration into multi-step synthetic sequences.

Synthesis

  • Route1
    • In-stock
      4-Tolylboronic acid|CS-W009284
      5720-05-8
    • null|null
      7697-37-2
    • ~75%
    • In-stock
      4-Methyl-3-nitrophenylboronic acid|CS-W000971
      80500-27-2

    References

    • Journal of the American Chemical Society, , vol. 54, p. 4415 - 4424
  • Route2

    References

    • Journal of the American Chemical Society, , vol. 54, p. 4415,4418
  • Route3
    • null|null
      4294-57-9
    • ~%
    • In-stock
      4-Methyl-3-nitrophenylboronic acid|CS-W000971
      80500-27-2

    References

    • Journal of the American Chemical Society, , vol. 54, p. 4415,4418

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   83.6
  • LogP   -0.41698
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   2

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