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

  • CAS No. 905300-76-7

  • Cat. No. CS-0046958
  • Purity≥97%
  • MDL No.MFCD07371552

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

tert-Butyl (2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate|CS-0046958

Structure of 905300-76-7

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General Information

  • CAS No. 905300-76-7
  • Cat. No. CS-0046958
  • Purity ≥97%
  • MDL No. MFCD07371552
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₂₈BNO₄
  • Molecular Weight 333.23
  • Synonym(s) tert-Butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylcarbamate
  • SMILES O=C(NCC1=C(B(OC2(C)C)OC2(C)C)C=CC=C1)OC(C)(C)C

Description

This boronate ester features a tert-butyl carbamate-protected benzyl scaffold, enabling stable, selective coupling in Suzuki-Miyaura reactions. The tetramethylboronate moiety ensures high reactivity and compatibility with diverse reaction conditions, while the protecting group remains intact under standard catalytic processes.

Application

tert-Butyl (2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate serves as a robust boron-based building block for Suzuki-Miyaura cross-coupling reactions. Its stable dioxaborolane moiety enables efficient C–C bond formation under mild conditions, while the tert-butoxycarbonyl (Boc) group provides orthogonal protection for primary amines. The compound exhibits excellent bench stability, facile purification, and broad functional group tolerance, making it ideal for late-stage diversification in medicinal chemistry and heterocycle synthesis.

Synthesis

  • Route1

    References

    • GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; HENDRICKSON, Thomas, Francis; HO, Koc-Kan; SAUNDERS, Michael, David; STEVENS, Brian, John; SWIERCZEK, Krzysztof; WRIGHT, Kevin, Bret Patent: WO2013/62945 A1, 2013 ; Location in patent: Page/Page column 132 ; WO 2013/062945 A1
  • Route2

    References

    • GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; HENDRICKSON, Thomas, Francis; HO, Koc-Kan; SAUNDERS, Michael, David; STEVENS, Brian, John; SWIERCZEK, Krzysztof; WRIGHT, Kevin, Bret Patent: WO2013/62945 A1, 2013 ; WO 2013/062945 A1
  • Route3

    References

    • GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; HENDRICKSON, Thomas, Francis; HO, Koc-Kan; SAUNDERS, Michael, David; STEVENS, Brian, John; SWIERCZEK, Krzysztof; WRIGHT, Kevin, Bret Patent: WO2013/62945 A1, 2013 ; WO 2013/062945 A1

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   56.79
  • LogP   3.0105
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   3

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