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4-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

  • CAS No. 779331-49-6

  • Cat. No. CS-0101373
  • Purity≥97%
  • MDL No.MFCD16994352

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

4-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol|CS-0101373

Structure of 779331-49-6

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General Information

  • CAS No. 779331-49-6
  • Cat. No. CS-0101373
  • Purity ≥97%
  • MDL No. MFCD16994352
  • Storage RT, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₆BFO₃
  • Molecular Weight 238.06
  • Synonym(s) 5-Fluoro-2-hydroxyphenylboronic acid, pinacol ester
  • SMILES OC1=CC=C(F)C=C1B2OC(C)(C)C(C)(C)O2

Description

4-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol features a boronate ester group conjugated to an electron-deficient aryl fluoride, enabling efficient Suzuki-Miyaura coupling. The tetramethyl-substituted dioxaborolane enhances stability and solubility in organic solvents. This bench-stable reagent integrates readily into complex molecule synthesis workflows.

Application

4-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol serves as a versatile boronate building block in Suzuki-Miyaura cross-coupling reactions. Its fluorinated aryl moiety enhances metabolic stability and modulates electronic properties, while the pinacol boronate group provides excellent bench stability, mild reaction conditions, and broad functional group tolerance. This reagent facilitates efficient C–C bond formation in the synthesis of biaryl scaffolds common in pharmaceutical and agrochemical research.

Synthesis

  • Route1

    References

    • Friedman, Adam A.; Panteleev, Jane; Tsoung, Jennifer; Huynh, Vaizanne; Lautens, Mark Angewandte Chemie - International Edition, 2013 , vol. 52, # 37 p. 9755 - 9758
  • Route2

    References

    • Friedman, Adam A.; Panteleev, Jane; Tsoung, Jennifer; Huynh, Vaizanne; Lautens, Mark Angewandte Chemie - International Edition, 2013 , vol. 52, # 37 p. 9755 - 9758

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-P280-P302+P352

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Computational Chemistry Data

  • TPSA   38.69
  • LogP   1.8305
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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