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(4-Hexylphenyl)boronic acid

  • CAS No. 105365-50-2

  • Cat. No. CS-0111834
  • Purity≥97%
  • MDL No.MFCD04039029

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

(4-Hexylphenyl)boronic acid|CS-0111834

Structure of 105365-50-2

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General Information

  • CAS No. 105365-50-2
  • Cat. No. CS-0111834
  • Purity ≥97%
  • MDL No. MFCD04039029
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₉BO₂
  • Molecular Weight 206.09
  • Synonym(s) 4-Hexylphenylboronic acid
  • SMILES OB(C1=CC=C(CCCCCC)C=C1)O

Description

(4-Hexylphenyl)boronic acid features a robust boronate moiety appended to a hydrophobic hexyl-substituted phenyl ring, enabling enhanced solubility in organic media and stability under standard conditions. This structure facilitates efficient Suzuki-Miyaura cross-coupling reactions, particularly in the synthesis of conjugated polymers and functionalized aryl architectures.

Application

(4-Hexylphenyl)boronic acid serves as a versatile building block in Suzuki-Miyaura coupling reactions, enabling efficient C–C bond formation under mild conditions. Its alkyl-substituted arylboronic acid structure offers enhanced solubility and bench stability compared to unsubstituted analogs, facilitating straightforward purification and handling. The hexyl chain imparts favorable lipophilicity for applications in materials science and medicinal chemistry, while maintaining compatibility with diverse functional groups.

Synthesis

  • Route1

    References

    • Mitsubishi Chemical Corporation; ISHIBASHI, Koichi; GOROHMARU, Hideki; SHIMIZU, Wataru; OKAMOTO, Tomomi Patent: EP2695882 A1, 2014 ; Location in patent: Paragraph 0377 ;
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      7647-01-0
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      121-43-7
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      1-Bromo-4-hexylbenzene|CS-0020120
      23703-22-2
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    • In-stock
      (4-Hexylphenyl)boronic acid|CS-0111834
      105365-50-2

    References

    • US2012/264732 A1, ; Page/Page column 7 ; US 20120264732 A1
  • Route3
    • null|null
      1355339-91-1
    • ~%
    • In-stock
      (4-Hexylphenyl)boronic acid|CS-0111834
      105365-50-2

    References

    • Journal of Materials Chemistry, , vol. 20, # 10 p. 1999 - 2006

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-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   40.46
  • LogP   1.4892
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   6

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