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6-Bromobenzo[d][1,3]dioxole-5-carboxylic acid

  • CAS No. 60546-62-5

  • Cat. No. CS-0094294
  • Purity≥96%
  • MDL No.MFCD00156994

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

6-Bromobenzo[d][1,3]dioxole-5-carboxylic acid|CS-0094294

Structure of 60546-62-5

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General Information

  • CAS No. 60546-62-5
  • Cat. No. CS-0094294
  • Purity ≥96%
  • MDL No. MFCD00156994
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅BrO₄
  • Molecular Weight 245.03
  • Synonym(s) Acide 6-bromo-1,3-benzodioxole-5-carboxylique
  • SMILES O=C(C1=C(Br)C=C(OCO2)C2=C1)O

Description

6-Bromobenzo[d][1,3]dioxole-5-carboxylic acid features a brominated benzodioxole core with a carboxylic acid handle at the 5-position, enabling direct conjugation in cross-coupling reactions. The electron-deficient aryl bromide integrates readily into Suzuki and Negishi transformations, while the ortho-dioxole moiety enhances solubility and stability under standard conditions.

Application

6-Bromobenzo[d][1,3]dioxole-5-carboxylic acid serves as a versatile building block in medicinal chemistry and materials science, enabling direct functionalization at the bromine site via palladium-catalyzed cross-coupling reactions. The carboxylic acid group facilitates derivatization through amide or ester formation, while the 1,3-dioxole ring imparts stability and orthogonality to common protecting group strategies. This compound exhibits excellent bench stability, clean purification profiles, and compatibility with standard synthetic workflows.

Synthesis

  • Route1

    References

    • Padwa, Albert; Dimitroff, Martin; Waterson, Alex G.; Wu, Tianhua Journal of Organic Chemistry, 1998 , vol. 63, # 12 p. 3986 - 3997
  • Route2

    References

    • Kobayashi, Shigeru; Imakura, Yasuhiro; Horikawa, Ritsuko Chemical & Pharmaceutical Bulletin, 1980 , vol. 28, # 4 p. 1287 - 1293
  • Route3
    • In-stock
      6-Bromobenzo[d][1,3]dioxole-5-carbaldehyde|CS-W005335
      15930-53-7
    • ~%
    • null|null
      6642-34-8
    • In-stock
      6-Bromobenzo[d][1,3]dioxole-5-carboxylic acid|CS-0094294
      60546-62-5

    References

    • Fales et al. Journal of the American Chemical Society, 1955 , vol. 77, p. 5885,5889

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-P280-P302+P352

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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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