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CS-W001157 4
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2-(3-Chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

  • CAS No. 929626-16-4

  • Cat. No. CS-0174431
  • Purity≥98%
  • MDL No.None

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

2-(3-Chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0174431

Structure of 929626-16-4

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General Information

  • CAS No. 929626-16-4
  • Cat. No. CS-0174431
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₈BClO₃
  • Molecular Weight 268.54
  • Synonym(s) 3-CHLORO-5-METHOXYPHENYLBORONIC ACID, PINACOL ESTER
  • SMILES CC1(C(C)(OB(O1)C2=CC(Cl)=CC(OC)=C2)C)C

Description

This boronate reagent features a chloro-methoxy-substituted aryl group enabling efficient cross-coupling in Suzuki-Miyaura reactions. The tetramethyl-dioxaborolane scaffold ensures excellent stability, solubility in common organic solvents, and compatibility with air- and moisture-tolerant protocols.

Application

2-(3-Chloro-5-methoxyphenyl)-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 3-chloro-5-methoxyphenyl moiety enables selective functionalization under standard catalytic conditions, with the tetramethyl-substituted dioxaborolane ring providing enhanced stability and ease of purification. Its compatibility with diverse reaction partners makes it a practical choice for constructing complex aryl architectures in medicinal chemistry and materials synthesis.

Synthesis

  • Route1
    • In-stock
      1-Chloro-3-methoxybenzene|CS-W018269
      2845-89-8
    • null|null
      25015-63-8
    • ~%
    • In-stock
      2-(3-Chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0174431
      929626-16-4

    References

    • Journal of the American Chemical Society, , vol. 125, # 26 p. 7792 - 7793
  • Route2

    References

    • Zeqing, Li; Zhibin, Liang; Yuqiang, Wang; Pei, Yu Research on Chemical Intermediates, 2013 , vol. 39, # 4 p. 1917 - 1926
  • Route3
    • 2-Triethylsilyl-4,4,5,5-Tetramethyl-1,3,2-dioxaborolane|CS-0770438
      745783-97-5
    • In-stock
      1-Chloro-3-methoxybenzene|CS-W018269
      2845-89-8
    • ~54%
    • In-stock
      2-(3-Chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0174431
      929626-16-4

    References

    • Boebel, Timothy A.; Hartwig, John F. Organometallics, 2008 , vol. 27, # 22 p. 6013 - 6019

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-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   27.69
  • LogP   2.6478
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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