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tert-Butyl 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate

  • CAS No. 262444-42-8

  • Cat. No. CS-0001977
  • Purity≥95%
  • MDL No.MFCD09033883

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

tert-Butyl 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate|CS-0001977

Structure of 262444-42-8

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General Information

  • CAS No. 262444-42-8
  • Cat. No. CS-0001977
  • Purity ≥95%
  • MDL No. MFCD09033883
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₇H₂₅BFNO₄
  • Molecular Weight 337.19
  • Synonym(s) Tert-Butyl-2-Fluoro-4-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-yl)Phenylcarbamate
  • SMILES O=C(OC(C)(C)C)NC1=C(F)C=C(C=C1)B(OC(C)2C)OC2(C)C

Description

tert-Butyl 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate is a bench-stable boronate ester featuring a fluoro-substituted aryl handle and a protected carbamate group. This structure enables efficient palladium-catalyzed cross-coupling reactions under standard conditions, facilitating the incorporation of fluorinated aromatic motifs into complex molecular architectures with high functional group tolerance.

Application

tert-Butyl 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The fluoro substituent enables directed ortho-metalation and facilitates downstream functionalization, while the boronate ester group offers excellent stability, ease of handling, and compatibility with diverse reaction conditions. The tert-butyl carbamate protects the amine, providing orthogonal functionality and simplifying purification. This reagent is particularly valuable in constructing biaryl scaffolds and heterocyclic motifs common in pharmaceutical research.

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   56.79
  • LogP   3.4719
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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