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tert-Butyl 3-{[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]methyl}azetidine-1-carboxylate

  • CAS No. 877399-31-0

  • Cat. No. CS-0048331
  • Purity≥97%
  • MDL No.None

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

tert-Butyl 3-{[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]methyl}azetidine-1-carboxylate|CS-0048331

Structure of 877399-31-0

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General Information

  • CAS No. 877399-31-0
  • Cat. No. CS-0048331
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₃₀BN₃O₄
  • Molecular Weight 363.26
  • Synonym(s) None
  • SMILES CC(C)(C)OC(=O)N1CC(CN2C=C(C=N2)B2OC(C)(C)C(C)(C)O2)C1

Description

tert-Butyl 3-{[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]methyl}azetidine-1-carboxylate features a pyrazole-borane moiety integrated with a sterically shielded azetidine scaffold, delivering enhanced stability and reactivity in Suzuki-Miyaura coupling processes. The tetramethylboronate group enables efficient cross-coupling under mild conditions, while the tert-butyl ester ensures compatibility with standard deprotection workflows. This compound serves as a modular building block for complex heterocyclic architectures in medicinal chemistry and materials science.

Application

tert-Butyl 3-{[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]methyl}azetidine-1-carboxylate serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The azetidine core provides a strained, bioactive scaffold, while the pyrazole moiety offers hydrogen-bonding capacity and metabolic stability. The tert-butyl carbamate group enables mild deprotection under acidic conditions, facilitating downstream functionalization. This compound exhibits excellent bench stability, tolerates diverse reaction conditions, and is readily purified by standard chromatography, making it ideal for iterative medicinal chemistry campaigns and API intermediate synthesis.

Safety Information

Download SDS
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   65.82
  • LogP   2.0492
  • H_Acceptors   6
  • H_Donors   0
  • Rotatable_Bonds   3

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