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CS-W001157 4
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N-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acrylamide

  • CAS No. 874363-18-5

  • Cat. No. CS-B1259
  • Purity≥98%
  • MDL No.MFCD22493996

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

N-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acrylamide|CS-B1259

Structure of 874363-18-5

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General Information

  • CAS No. 874363-18-5
  • Cat. No. CS-B1259
  • Purity ≥98%
  • MDL No. MFCD22493996
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₀BNO₃
  • Molecular Weight 273.14
  • Synonym(s) 3-Acrylamidophenylboronic Acid Pinacol Ester
  • SMILES C=CC(NC1=CC=CC(B2OC(C)(C)C(C)(C)O2)=C1)=O

Description

N-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acrylamide features a boronate ester handle conjugated to an acrylamide warhead, enabling efficient Suzuki-Miyaura coupling and site-specific bioconjugation. This bench-stable reagent integrates readily into peptide and small-molecule scaffolds under mild conditions, delivering precise functionalization in synthetic and medicinal chemistry workflows.

Application

N-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acrylamide serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The arylboronate moiety enables efficient C–C bond formation under mild conditions, while the acrylamide functionality provides conjugated reactivity and potential for downstream transformations. Bench-stable and compatible with diverse functional groups, it facilitates rapid assembly of biaryl and extended π-conjugated architectures in medicinal chemistry and materials synthesis.

Safety Information

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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   47.56
  • LogP   2.1103
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   3

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