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CS-W001157 4
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2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

  • CAS No. 461699-81-0

  • Cat. No. CS-0041457
  • Purity≥97%
  • MDL No.MFCD06795657

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

2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|CS-0041457

Structure of 461699-81-0

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General Information

  • CAS No. 461699-81-0
  • Cat. No. CS-0041457
  • Purity ≥97%
  • MDL No. MFCD06795657
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₂₀BNO₃
  • Molecular Weight 249.11
  • Synonym(s) 4'-METHYL4-AMINO-3-METHOXYPHENYLBORONIC ACID, PINACOL ESTER
  • SMILES COC1=C(N)C=CC(=C1)B1OC(C)(C)C(C)(C)O1

Description

2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline features a boronate ester group enabling robust Suzuki-Miyaura coupling under mild conditions. The methoxy substituent enhances electron density at the aromatic ring, improving reactivity in cross-coupling reactions. This bench-stable compound integrates seamlessly into complex molecular architectures with minimal purification needs.

Application

2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The ortho-methoxy group provides electronic modulation and enhances solubility, while the pinacol boronate ester offers excellent stability and compatibility with diverse reaction conditions. It facilitates efficient C–C bond formation under mild catalytic conditions, enabling rapid access to substituted anilines and biaryl scaffolds in medicinal chemistry and materials synthesis.

Synthesis

  • Route1

    References

    • US2005/20619 A1, ; Page 40-41 ; US 20050020619 A1
  • Route2
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    • In-stock
      2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|CS-0041457
      461699-81-0

    References

    • US2008/269523 A1, ; Page/Page column 6 ;
  • Route3

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 21, # 3 p. 966 - 970

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   53.71
  • LogP   1.5766
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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