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2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,4-oxadiazole

  • CAS No. 276694-19-0

  • Cat. No. CS-0161639
  • Purity≥97%
  • MDL No.MFCD11865277

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

2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,4-oxadiazole|CS-0161639

Structure of 276694-19-0

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General Information

  • CAS No. 276694-19-0
  • Cat. No. CS-0161639
  • Purity ≥97%
  • MDL No. MFCD11865277
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₇BN₂O₃
  • Molecular Weight 272.11
  • Synonym(s) 2-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL]-1,3,4-OXADIAZOLE
  • SMILES CC1(C)C(C)(C)OB(C2=CC=C(C3=NN=CO3)C=C2)O1

Description

This oxadiazole derivative features a boronate ester group enabling efficient Suzuki-Miyaura coupling under standard conditions. The 1,3,4-oxadiazole ring imparts metabolic stability and enhances solubility, while the tetramethylcyclopentadienylboronate moiety ensures high reactivity and bench-stable handling.

Application

2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,4-oxadiazole serves as a versatile boronate building block for palladium-catalyzed cross-coupling reactions. Its stable dioxaborolane group enables efficient Suzuki-Miyaura coupling with aryl halides and pseudohalides, facilitating the construction of biaryl scaffolds common in pharmaceutical and agrochemical research. The 1,3,4-oxadiazole ring provides metabolic stability and hydrogen-bonding capacity, enhancing its utility in medicinal chemistry lead optimization. Bench-stable and easily purified by flash chromatography, it functions reliably in multi-step syntheses requiring functional group tolerance and predictable reactivity.

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

Quality Control

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Computational Chemistry Data

  • TPSA   57.38
  • LogP   2.0358
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   2

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