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

  • CAS No. 468060-28-8

  • Cat. No. CS-0107772
  • Purity≥97%
  • MDL No.None

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

tert-Butyl (E)-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl)carbamate|CS-0107772

Structure of 468060-28-8

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General Information

  • CAS No. 468060-28-8
  • Cat. No. CS-0107772
  • Purity ≥97%
  • MDL No. None
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₂₆BNO₄
  • Molecular Weight 283.17
  • Synonym(s) (E)-tert-butyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl)carbamate
  • SMILES O=C(NC/C=C/B1OC(C)(C(C)(C)O1)C)OC(C)(C)C

Description

tert-Butyl (E)-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl)carbamate delivers a bench-stable, moisture-tolerant boronate handle with defined E-geometry. This allylboronate integrates seamlessly into cross-coupling reactions, enabling efficient construction of complex alkenyl architectures under standard conditions. The protecting group remains intact during catalytic transformations, simplifying purification and enhancing functional group compatibility.

Application

tert-Butyl (E)-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl)carbamate serves as a stable, bench-ready allylboron building block for palladium-catalyzed cross-coupling reactions. Its E-configured vinyl boronate enables stereoselective C–C bond formation with aryl and vinyl halides, while the tert-butyl carbamate group provides excellent functional group tolerance and facilitates purification. This reagent is particularly valuable in the synthesis of complex alkenes and heterocyclic scaffolds within medicinal chemistry and process development workflows.

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   3.3348
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   3

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