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CS-W001157 4
Total: USD 88.00

(E)-2-(3-Chlorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

  • CAS No. 871125-84-7

  • Cat. No. CS-W014057
  • Molecule weight264.56
  • Purity≥98%
  • MDL No.MFCD08276867

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

(E)-2-(3-Chlorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W014057

Structure of 871125-84-7

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General Information

  • CAS No. 871125-84-7
  • Cat. No. CS-W014057
  • Purity ≥98%
  • MDL No. MFCD08276867
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₈BClO₂
  • Molecular Weight 264.56
  • Synonym(s) TRANS-2-(3-CHLOROPHENYL)VINYLBORONIC AC&
  • SMILES CC1(C)C(C)(C)OB(/C=C/C2=CC=CC(Cl)=C2)O1

Description

This boronate ester features a (E)-configured chlorostyryl moiety integrated with a stable tetramethyl-1,3,2-dioxaborolane ring. The configuration enhances regioselectivity in cross-coupling reactions, while the steric shielding of the dioxaborolane group ensures bench-stable handling and resistance to hydrolysis under standard conditions.

Application

(E)-2-(3-Chlorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. Its (E)-configured vinylboronate enables stereoselective formation of conjugated styrenyl scaffolds, with tolerance to common functional groups and straightforward purification via flash chromatography. This reagent facilitates efficient access to substituted biaryl and styrenyl architectures relevant to pharmaceutical and materials chemistry.

Synthesis

  • Route1
    • In-stock
      3-Chlorophenylacetylene|CS-W004103
      766-83-6
    • null|null
      25015-63-8
    • ~97%
    • In-stock
      (E)-2-(3-Chlorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W014057
      871125-84-7

    References

    • Haberberger, Michael; Enthaler, Stephan Chemistry - An Asian Journal, 2013 , vol. 8, # 1 p. 50 - 54

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   18.46
  • LogP   3.9846
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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