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

  • CAS No. 159624-15-4

  • Cat. No. CS-0112317
  • Molecule weight319.20
  • Purity≥97%
  • MDL No.MFCD03411943

*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)phenyl)carbamate|CS-0112317

Structure of 159624-15-4

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General Information

  • CAS No. 159624-15-4
  • Cat. No. CS-0112317
  • Purity ≥97%
  • MDL No. MFCD03411943
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₇H₂₆BNO₄
  • Molecular Weight 319.20
  • Synonym(s) (2-boc-aminophenyl)boronic acid, pinacol ester
  • SMILES O=C(OC(C)(C)C)NC1=CC=CC=C1B2OC(C)(C)C(C)(C)O2

Description

tert-Butyl (2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate delivers a boronate group flanked by a sterically protected dioxaborolane and a bench-stable carbamate. This combination enables reliable coupling in Suzuki-Miyaura reactions while minimizing side processes. The protecting group remains intact under standard reaction conditions, simplifying purification and enabling efficient access to functionalized biaryls.

Application

tert-Butyl (2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. The protected amine functionality enables direct incorporation into biaryl scaffolds with high functional group tolerance, while the robust boronate ester resists hydrolysis and facilitates purification. Its compatibility with diverse reaction conditions makes it ideal for late-stage functionalization in medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • Journal of Organic Chemistry, , vol. 65, # 26 p. 9268 - 9271
  • Route2

    References

    • Colobert, Francoise; Valdivia, Victoria; Choppin, Sabine; Leroux, Frederic R.; Fernandez, Inmaculada; Alvarez, Eleuterio; Khiar, Noureddine Organic Letters, 2009 , vol. 11, # 22 p. 5130 - 5133
  • Route3

    References

    • Journal of Organic Chemistry, , vol. 65, # 26 p. 9268 - 9271

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   56.79
  • LogP   3.3328
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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