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3-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

  • CAS No. 1418130-40-1

  • Cat. No. CS-0119466
  • Purity≥97%
  • MDL No.MFCD24039674

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

3-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|CS-0119466

Structure of 1418130-40-1

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General Information

  • CAS No. 1418130-40-1
  • Cat. No. CS-0119466
  • Purity ≥97%
  • MDL No. MFCD24039674
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₇BFNO₂
  • Molecular Weight 237.08
  • Synonym(s) UXLMPHNFBMXVGJ-UHFFFAOYSA-N
  • SMILES NC1=CC=CC(F)=C1B2OC(C)(C)C(C)(C)O2

Description

3-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline features a boronate ester group flanked by electron-rich tetramethylcyclopentadienone rings, enabling stable coupling under mild conditions. The para-fluoro substitution enhances metabolic stability and modulates electronic properties. This bench-stable reagent integrates seamlessly into Suzuki-Miyaura cross-coupling workflows for constructing arylated heterocycles and bioactive scaffolds.

Application

3-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The ortho-borylated aniline moiety enables efficient C–C bond formation under mild conditions, with excellent functional group tolerance and bench stability. Its tetramethyl-substituted dioxaborolane enhances reactivity and minimizes protodeboronation, facilitating reliable coupling in complex molecule 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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   44.48
  • LogP   1.7071
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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