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CS-W001157 4
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5-Bromobenzo[1,3]dioxole-4-carboxylic acid

  • CAS No. 72744-56-0

  • Cat. No. CS-0195091
  • Purity≥96%
  • MDL No.None

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

5-Bromobenzo[1,3]dioxole-4-carboxylic acid|CS-0195091

Structure of 72744-56-0

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General Information

  • CAS No. 72744-56-0
  • Cat. No. CS-0195091
  • Purity ≥96%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅BrO₄
  • Molecular Weight 245.03
  • Synonym(s) 5-bromobenzo[d][1,3]dioxole-4-carboxylic acid
  • SMILES C1=CC2=C(C(=C1Br)C(=O)O)OCO2

Description

5-Bromobenzo[1,3]dioxole-4-carboxylic acid features a brominated benzodioxole core with a carboxylic acid group at the 4-position, offering a robust scaffold for synthetic diversification. This electron-deficient aromatic system enables efficient coupling reactions and integrates readily into bioactive molecules. The compound exhibits excellent stability under standard bench conditions and is compatible with common functional group manipulations in medicinal chemistry workflows.

Application

5-Bromobenzo[1,3]dioxole-4-carboxylic acid serves as a versatile building block in medicinal chemistry and synthetic organic chemistry. Its structure combines a brominated benzodioxole ring with a carboxylic acid group, enabling facile coupling reactions via Suzuki-Miyaura or Stille cross-coupling protocols. The compound exhibits good bench stability, moderate solubility in common organic solvents, and tolerates a range of functional groups, facilitating its use in the synthesis of complex heterocyclic scaffolds and bioactive molecules.

Synthesis

  • Route1

    References

    • Bernardo, Paul H.; Wan, Kah-Fei; Sivaraman, Thirunavukkarasu; Xu, Jin; Moore, Felicity K.; Hung, Alvin W.; Mok, Henry Y. K.; Yu, Victor C.; Chai, Christina L. L. Journal of Medicinal Chemistry, 2008 , vol. 51, # 21 p. 6699 - 6710
  • Route2
    • In-stock
      5-Bromo-1,3-benzodioxole|CS-W008826
      2635-13-4
    • null|null
      124-38-9
    • ~82%
    • In-stock
      5-Bromobenzo[1,3]dioxole-4-carboxylic acid|CS-0195091
      72744-56-0

    References

    • Sit, Sing-Yuen; Xie, Kai; Jacutin-Porte, Swanee; Boy, Kenneth M.; Seanz, James; Taber, Matthew T.; Gulwadi, Amit G.; Korpinen, Carolyn D.; Burris, Kevin D.; Molski, Thaddeus F.; Ryan, Elaine; Xu, Cen; Verdoorn, Todd; Johnson, Graham; Nichols, David E.; Mailman, Richard B. Bioorganic and Medicinal Chemistry, 2004 , vol. 12, # 4 p. 715 - 734
  • Route3

    References

    • Smidrkal, Jan Collection of Czechoslovak Chemical Communications, 1982 , vol. 47, # 8 p. 2140 - 2144

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   55.76
  • LogP   1.876
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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