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CS-W001157 4
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(2-((Phenylamino)methyl)phenyl)boronic acid

  • CAS No. 327096-48-0

  • Cat. No. CS-0173963
  • Purity≥98%
  • MDL No.None

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

(2-((Phenylamino)methyl)phenyl)boronic acid|CS-0173963

Structure of 327096-48-0

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General Information

  • CAS No. 327096-48-0
  • Cat. No. CS-0173963
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₄BNO₂
  • Molecular Weight 227.07
  • Synonym(s) 2-(N-Phenylaminomethyl)phenylboronic acid
  • SMILES OB(O)C1=CC=CC=C1CNC2=CC=CC=C2

Description

This boronate reagent features a phenylamino-methyl tethered to a phenylboronic acid core, enabling efficient coupling in Suzuki-Miyaura reactions. The amine-functionalized aryl handle enhances solubility and facilitates downstream derivatization. Bench-stable under standard conditions, it integrates readily into complex molecular architectures.

Application

(2-((Phenylamino)methyl)phenyl)boronic acid serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, enabling efficient C–C bond formation under mild conditions. Its ortho-aminomethyl-substituted arylboronic acid structure offers enhanced stability and compatibility with diverse functional groups, facilitating the synthesis of biaryl scaffolds relevant to medicinal chemistry and materials science. The molecule exhibits good bench stability and straightforward purification, making it well-suited for iterative synthetic workflows.

Synthesis

  • Route1
    • In-stock
      (2-Formylphenyl)boronic acid|CS-W007320
      40138-16-7
    • null|null
      74497-02-2
    • ~71%
    • In-stock
      (2-((Phenylamino)methyl)phenyl)boronic acid|CS-0173963
      327096-48-0

    References

    • Luvino, Delphine; Smietana, Michael; Vasseur, Jean-Jacques Tetrahedron Letters, 2006 , vol. 47, # 52 p. 9253 - 9256
  • Route2

    References

    • Arimori, Susumu; Bosch, Laurence I.; Ward, Christopher J.; James, Tony D. Tetrahedron Letters, 2001 , vol. 42, # 27 p. 4553 - 4555
  • Route3
    • null|null
      74497-02-2
    • ~%
    • In-stock
      (2-((Phenylamino)methyl)phenyl)boronic acid|CS-0173963
      327096-48-0

    References

    • Bosch; Fyles; James Tetrahedron, 2004 , vol. 60, # 49 p. 11175 - 11190

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   52.49
  • LogP   0.9785
  • H_Acceptors   3
  • H_Donors   3
  • Rotatable_Bonds   4

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