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CS-W001157 4
Total: USD 88.00

(4-Cyano-3-methoxyphenyl)boronic acid

  • CAS No. 677777-45-6

  • Cat. No. CS-W005859
  • Purity≥95%
  • MDL No.MFCD10696655

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

(4-Cyano-3-methoxyphenyl)boronic acid|CS-W005859

Structure of 677777-45-6

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General Information

  • CAS No. 677777-45-6
  • Cat. No. CS-W005859
  • Purity ≥95%
  • MDL No. MFCD10696655
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₈BNO₃
  • Molecular Weight None
  • Synonym(s) Boronic acid, (4-cyano-3-methoxyphenyl)- (9CI)
  • SMILES COC1=C(C=CC(=C1)B(O)O)C#N

Description

This boronic acid features a cyano group para to the boronate, enhancing electrophilic reactivity in Suzuki-Miyaura couplings. The methoxy substituent improves solubility and stability under standard conditions, enabling efficient cross-coupling with aryl halides and triflates.

Application

(4-Cyano-3-methoxyphenyl)boronic acid serves as a versatile building block in Suzuki-Miyaura coupling reactions, enabling efficient C–C bond formation under mild conditions. Its orthogonal functional group tolerance—retaining stable cyano and methoxy moieties—facilitates downstream derivatization in medicinal chemistry and materials science. The boronic acid exhibits excellent bench stability and is readily purified by recrystallization, making it ideal for high-throughput synthesis and scale-up applications.

Synthesis

  • Route1

    References

    • VERTEX PHARMACEUTICALS INCORPORATED? Patent: WO2005/95400 A1, 2005 ; Location in patent: Page/Page column 341 ; WO 2005/095400 A1

Safety Information

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Computational Chemistry Data

  • TPSA   73.48
  • LogP   -0.75332
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   2

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