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

  • CAS No. 833486-94-5

  • Cat. No. CS-0130354
  • Purity≥95%
  • MDL No.None

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

2-Nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|CS-0130354

Structure of 833486-94-5

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General Information

  • CAS No. 833486-94-5
  • Cat. No. CS-0130354
  • Purity ≥95%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₇BN₂O₄
  • Molecular Weight 264.09
  • Synonym(s) 4-Amino-3-nitrophenylboronic Acid Pinacol Ester
  • SMILES NC1=CC=C(C=C1[N+]([O-])=O)B2OC(C)(C(C)(O2)C)C

Description

2-Nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline features a boronate ester group enabling efficient Suzuki-Miyaura coupling, paired with a nitro functionality that enhances reactivity in cross-coupling and functionalization workflows. This bench-stable compound integrates seamlessly into complex molecular architectures.

Application

2-Nitro-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 nitro group enables subsequent reduction to an amine, facilitating access to substituted anilines and heterocyclic scaffolds. Its tetramethyl-substituted boronate moiety offers excellent bench stability, functional group tolerance, and compatibility with standard coupling conditions, making it well-suited for iterative synthesis in medicinal chemistry and materials science workflows.

Synthesis

  • Route1

    References

    • US2007/117818 A1, ; Page/Page column 11-12 ; US 20070117818 A1

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

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Computational Chemistry Data

  • TPSA   87.62
  • LogP   1.4762
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   2

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