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4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine

  • CAS No. 882670-69-1

  • Cat. No. CS-0030610
  • Purity≥97%
  • MDL No.MFCD05663859

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

4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine|CS-0030610

Structure of 882670-69-1

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General Information

  • CAS No. 882670-69-1
  • Cat. No. CS-0030610
  • Purity ≥97%
  • MDL No. MFCD05663859
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₂₀BNO₂
  • Molecular Weight 233.11
  • Synonym(s) 5-Amino-2-Methylphenylboronic Acid,Pinacol Ester
  • SMILES NC1=CC=C(C)C(B2OC(C)(C)C(C)(C)O2)=C1

Description

4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine features a boronate ester group enabling reliable Suzuki-Miyaura coupling under mild conditions. The methyl and amine substituents provide orthogonal reactivity, while the tetramethylcyclopentadienone-derived boronate enhances stability and shelf life. This compound integrates seamlessly into complex molecular architectures with minimal purification needs.

Application

4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. Its ortho-methyl group enhances metabolic stability in bioactive scaffolds, while the pinacol boronate moiety ensures excellent bench stability and compatibility with diverse reaction conditions. The amine functionality enables direct incorporation into pharmaceutical intermediates and functionalized heterocycles.

Synthesis

  • Route1

    References

    • Kyowa Hakko Kirin Co., Ltd. Patent: EP2269993 A1, 2011 ; Location in patent: Page/Page column 52 ;

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
Precautionary Statements : P264-P280-P302+P352-P362

Quality Control

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Computational Chemistry Data

  • TPSA   44.48
  • LogP   1.87642
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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