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tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylate

  • CAS No. 935278-73-2

  • Cat. No. CS-0146977
  • Purity≥97%
  • MDL No.MFCD11504966

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

tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylate|CS-0146977

Structure of 935278-73-2

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General Information

  • CAS No. 935278-73-2
  • Cat. No. CS-0146977
  • Purity ≥97%
  • MDL No. MFCD11504966
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₄BNO₄
  • Molecular Weight 293.17
  • Synonym(s) 2-Methyl-2-propanyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylate
  • SMILES O=C(N1C=C(B2OC(C)(C)C(C)(C)O2)C=C1)OC(C)(C)C

Description

tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylate features a boronate ester group integrated into a pyrrole scaffold, enabling efficient cross-coupling reactions. The tetramethyl-substituted dioxaborolane moiety enhances stability and reactivity under standard conditions. This bench-stable reagent facilitates the construction of complex heterocyclic architectures in synthetic and medicinal chemistry workflows.

Application

tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylate serves as a stable, bench-friendly boron building block for palladium-catalyzed cross-coupling reactions. The tetramethylborolane moiety enables efficient Suzuki-Miyaura coupling under mild conditions, while the tert-butyl ester provides orthogonal protection and facile deprotection. This reagent facilitates rapid access to functionalized pyrrole scaffolds prevalent in medicinal chemistry and materials science.

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   49.69
  • LogP   2.5705
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   1

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