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CS-W001157 4
Total: USD 88.00

(4'-(pentyloxy)-[1,1'-biphenyl]-4-yl)boronic acid

  • CAS No. 158937-25-8

  • Cat. No. CS-W004379
  • Purity≥98%
  • MDL No.MFCD07644475

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

(4'-(pentyloxy)-[1,1'-biphenyl]-4-yl)boronic acid|CS-W004379

Structure of 158937-25-8

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General Information

  • CAS No. 158937-25-8
  • Cat. No. CS-W004379
  • Purity ≥98%
  • MDL No. MFCD07644475
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₇H₂₁BO₃
  • Molecular Weight 284.16
  • Synonym(s) 4'-Amyloxybiphenyl-4-boronic Acid (contains varying amounts of Anhydride)
  • SMILES CCCCCOc1ccc(cc1)-c1ccc(cc1)B(O)O

Description

This boronate moiety integrates a pentyloxy-substituted biphenyl scaffold, offering enhanced solubility and stability in organic media. The electron-rich aryl system facilitates efficient Suzuki-Miyaura coupling under standard conditions, enabling robust C–C bond formation in complex molecule synthesis.

Application

(4'-(pentyloxy)-[1,1'-biphenyl]-4-yl)boronic acid serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, enabling the efficient construction of biaryl scaffolds under mild conditions. The pentyloxy substituent enhances solubility and stability, while the boronic acid group exhibits reliable reactivity with aryl halides and triflates. Its bench-stable nature and compatibility with diverse functional groups make it well-suited for medicinal chemistry campaigns and process-scale synthesis.

Synthesis

  • Route1
    • 4-bromo-4'-(pentyloxy)-1,1'-biphenyl|CS-W004378
      63619-51-2
    • ~94%
    • In-stock
      (4'-(pentyloxy)-[1,1'-biphenyl]-4-yl)boronic acid|CS-W004379
      158937-25-8

    References

    • Yao, Jianzhong; Liu, Hongming; Zhou, Ting; Chen, Hai; Miao, Zhenyuan; Sheng, Chunquan; Zhang, Wannian European Journal of Medicinal Chemistry, 2012 , vol. 50, p. 196 - 208
  • Route2
    • null|null
      5419-55-6
    • 4-bromo-4'-(pentyloxy)-1,1'-biphenyl|CS-W004378
      63619-51-2
    • ~93%
    • In-stock
      (4'-(pentyloxy)-[1,1'-biphenyl]-4-yl)boronic acid|CS-W004379
      158937-25-8

    References

    • Clariant GmbH Patent: EP1156997 B1, 2004 ; Location in patent: Page 12 ;
  • Route3
    • null|null
      110-53-2
    • ~%
    • In-stock
      (4'-(pentyloxy)-[1,1'-biphenyl]-4-yl)boronic acid|CS-W004379
      158937-25-8

    References

    • Yao, Jianzhong; Liu, Hongming; Zhou, Ting; Chen, Hai; Miao, Zhenyuan; Sheng, Chunquan; Zhang, Wannian European Journal of Medicinal Chemistry, 2012 , vol. 50, p. 196 - 208

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

Quality Control

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Computational Chemistry Data

  • TPSA   49.69
  • LogP   2.6024
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   7

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