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tert-Butyl (5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)carbamate

  • CAS No. 910462-31-6

  • Cat. No. CS-0046250
  • Purity≥97%
  • MDL No.None

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

tert-Butyl (5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)carbamate|CS-0046250

Structure of 910462-31-6

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General Information

  • CAS No. 910462-31-6
  • Cat. No. CS-0046250
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₆H₂₅BN₂O₄
  • Molecular Weight 320.19
  • Synonym(s) tert-butyl [5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]carbamate
  • SMILES O=C(OC(C)(C)C)NC1=NC=C(B2OC(C)(C)C(C)(C)O2)C=C1

Description

tert-Butyl (5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)carbamate is a bench-stable boronate ester featuring a pyridine scaffold with a protected amine. This reagent enables efficient Suzuki-Miyaura coupling under mild conditions, combining high functional group tolerance with ease of handling. The tetramethyl-dioxaborolane moiety ensures stability and low toxicity, while the tert-butyl carbamate group provides orthogonal protection for nitrogen-based transformations.

Application

tert-Butyl (5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)carbamate serves as a stable, bench-ready boron building block for palladium-catalyzed cross-coupling reactions. The pyridine core enables versatile functionalization in medicinal chemistry and materials science, while the Bpin group facilitates efficient Suzuki-Miyaura coupling under mild conditions. The tert-butyl carbamate protects the amine selectively, offering orthogonal handling and ease of removal post-coupling. This reagent exhibits excellent functional group tolerance and reproducible yields in standard synthetic workflows.

Synthesis

  • Route1

    References

    • AMBIT BIOSCIENCES CORPORATION; ABRAHAM, Sunny; HOLLADAY, Mark, W.; LIU, Gang; XU, Shimin Patent: WO2011/22473 A1, 2011 ; Location in patent: Page/Page column 127 ; WO 2011/022473 A1
  • Route2

    References

    • WO2006/97474 A1, ; Page/Page column 135 ;

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   69.68
  • LogP   2.7278
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   2

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