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

  • CAS No. 578729-05-2

  • Cat. No. CS-0093906
  • Molecule weight347.26
  • Purity≥95%
  • MDL No.None

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

tert-Butyl (R)-(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)carbamate|CS-0093906

Structure of 578729-05-2

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General Information

  • CAS No. 578729-05-2
  • Cat. No. CS-0093906
  • Purity ≥95%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₉H₃₀BNO₄
  • Molecular Weight 347.26
  • Synonym(s) (R)-tert-butyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamate
  • SMILES O=C(OC(C)(C)C)N[C@@H](C1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1)C

Description

tert-Butyl (R)-(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)carbamate delivers a chiral boronate handle with enhanced stability and compatibility in Suzuki-Miyaura coupling. The bulky tert-butyl carbamate group ensures excellent bench stability and minimizes side reactions, while the tetramethyl-1,3,2-dioxaborolane moiety enables efficient cross-coupling under mild conditions. This reagent integrates seamlessly into complex molecule synthesis workflows.

Application

tert-Butyl (R)-(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)carbamate serves as a stable, bench-ready boron building block for Suzuki-Miyaura coupling reactions. Its chiral benzylic center and orthogonal protecting group allow selective functionalization in complex molecule synthesis. The Bpin group enables reliable cross-coupling under mild conditions, while the tert-butyl carbamate offers excellent stability and straightforward deprotection via acidolysis, facilitating efficient access to chiral biaryl intermediates.

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   56.79
  • LogP   3.5715
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   3

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