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CS-W001157 4
Total: USD 88.00

(2-(Dimethylamino)phenyl)boronic acid

  • CAS No. 89291-23-6

  • Cat. No. CS-0176064
  • Purity≥97%
  • MDL No.None

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

(2-(Dimethylamino)phenyl)boronic acid|CS-0176064

Structure of 89291-23-6

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General Information

  • CAS No. 89291-23-6
  • Cat. No. CS-0176064
  • Purity ≥97%
  • MDL No. None
  • Storage RT, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₂BNO₂
  • Molecular Weight 165.00
  • Synonym(s) 2-(Dimethylamino)phenylboronic acid
  • SMILES CN(C1=CC=CC=C1B(O)O)C

Description

This boronic acid features a dimethylamino-substituted phenyl ring, enhancing electron density and improving reactivity in Suzuki-Miyaura coupling. The pendant boronic acid group enables efficient cross-coupling under mild conditions, delivering arylated products with high fidelity. Designed for stability and ease of handling, it integrates seamlessly into complex molecular architectures.

Application

(2-(Dimethylamino)phenyl)boronic acid serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, enabling efficient construction of biaryl scaffolds under mild conditions. Its ortho-dimethylaminophenyl motif offers enhanced solubility and electronic modulation, while the boronic acid group provides reliable reactivity with aryl halides and triflates. The compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Journal of Organic Chemistry, , vol. 73, # 16 p. 6330 - 6340
  • Route2
    • null|null
      121-43-7
    • null|null
      121-69-7
    • ~45%
    • In-stock
      (2-(Dimethylamino)phenyl)boronic acid|CS-0176064
      89291-23-6

    References

    • Lauer, Manfred; Wulff, Guenter Journal of Organometallic Chemistry, 1983 , vol. 256, # 1 p. 1 - 10
  • Route3
    • null|null
      313220-10-9
    • ~%
    • In-stock
      (2-(Dimethylamino)phenyl)boronic acid|CS-0176064
      89291-23-6

    References

    • Synlett, , # 18 p. 2846 - 2850

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   43.7
  • LogP   -0.5676
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   2

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