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CS-W001157 4
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(E)-2-(4-Fluorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

  • CAS No. 504433-86-7

  • Cat. No. CS-W012675
  • Purity≥95%
  • MDL No.MFCD12546189

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

(E)-2-(4-Fluorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W012675

Structure of 504433-86-7

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General Information

  • CAS No. 504433-86-7
  • Cat. No. CS-W012675
  • Purity ≥95%
  • MDL No. MFCD12546189
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₈BFO₂
  • Molecular Weight 248.10
  • Synonym(s) 4-Fluoro-Trans-Beta-Styrylboronic Acid Pinacol Ester
  • SMILES CC1(C)C(C)(C)OB(/C=C/C2=CC=C(F)C=C2)O1

Description

(E)-2-(4-Fluorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane features a stable boronate ester coupled to an (E)-configured fluoro-substituted styrenyl group. This configuration enhances regioselectivity in Suzuki-Miyaura couplings, enabling efficient C–C bond formation under mild conditions. The tetramethyl substituents confer exceptional bench stability and moisture tolerance, simplifying handling in synthetic workflows.

Application

(E)-2-(4-Fluorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. The (E)-configured styryl moiety enables stereoselective coupling with aryl and heteroaryl halides, facilitating efficient construction of conjugated biaryl systems. Its tetramethyl-substituted dioxaborolane ring enhances stability and minimizes protodeboronation, while the fluorine substituent offers orthogonal reactivity for downstream functionalization in medicinal chemistry and materials synthesis.

Synthesis

  • Route1
    • In-stock
      2,3-Dimethylbutane-2,3-diol|CS-0015356
      76-09-5
    • null|null
      1065498-68-1
    • ~%
    • In-stock
      (E)-2-(4-Fluorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W012675
      504433-86-7

    References

    • Peng, Ai-Yun; Chen, Ba-Tian; Chen, Pei-Jiang Journal of Fluorine Chemistry, 2013 , vol. 151, p. 58 - 62
  • Route2

    References

    • Zhao, Jie; Niu, Zhiqiang; Fu, Hua; Li, Yadong Chemical Communications, 2014 , vol. 50, # 16 p. 2058 - 2060
  • Route3

    References

    • Jang, Hwanjong; Zhugralin, Adil R.; Lee, Yunmi; Hoveyda, Amir H. Journal of the American Chemical Society, 2011 , vol. 133, # 20 p. 7859 - 7871

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-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P363-P501

Quality Control

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Computational Chemistry Data

  • TPSA   18.46
  • LogP   3.4703
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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