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CS-W001157 4
Total: USD 88.00

4-Bromo-2,6-dimethylbenzoic acid

  • CAS No. 74346-19-3

  • Cat. No. CS-W006638
  • Purity≥98%
  • MDL No.MFCD09965997

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

4-Bromo-2,6-dimethylbenzoic acid|CS-W006638

Structure of 74346-19-3

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General Information

  • CAS No. 74346-19-3
  • Cat. No. CS-W006638
  • Purity ≥98%
  • MDL No. MFCD09965997
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₉BrO₂
  • Molecular Weight 229.07
  • Synonym(s) None
  • SMILES BrC1=CC(=C(C(=O)O)C(=C1)C)C

Description

4-Bromo-2,6-dimethylbenzoic acid features a bromine atom at the para position relative to the carboxylic acid group, flanked by two methyl substituents at the ortho positions. This steric and electronic profile enhances stability and directs electrophilic substitution reactions with high regioselectivity. The compound serves as a key intermediate in pharmaceutical synthesis and functional material design.

Application

4-Bromo-2,6-dimethylbenzoic acid serves as a versatile building block in medicinal chemistry and synthetic organic chemistry. Its electron-deficient aromatic core, combined with orthogonal functional handles—bromine for cross-coupling and carboxylic acid for derivatization—enables efficient construction of complex scaffolds. The methyl groups enhance steric control and metabolic stability, while the compound exhibits excellent bench stability and ease of purification, facilitating integration into standard coupling and amide formation protocols.

Synthesis

  • Route1
    • null|null
      124-38-9
    • In-stock
      5-Bromo-2-iodo-m-xylene|CS-W005341
      206559-43-5
    • ~85%
    • In-stock
      4-Bromo-2,6-dimethylbenzoic acid|CS-W006638
      74346-19-3

    References

    • Ball, Matthew; Boyd, Alistair; Churchill, Gwydion; Cuthbert, Murray; Drew, Mark; Fielding, Mark; Ford, Gair; Frodsham, Lianne; Golden, Michael; Leslie, Kevin; Lyons, Sarah; McKeever-Abbas, Ben; Stark, Andrew; Tomlin, Paula; Gottschling, Stephen; Hajar, Abraham; Jiang, Ji-Long; Lo, Josephine; Suchozak, Bob Organic Process Research and Development, 2012 , vol. 16, # 5 p. 741 - 747
  • Route2

    References

    • Journal of the American Chemical Society, , vol. 63, p. 1679,1681
  • Route3
    • 4-Bromo-2,6-dimethylbenzamide|CS-0751823
      132949-41-8
    • ~%
    • In-stock
      4-Bromo-2,6-dimethylbenzoic acid|CS-W006638
      74346-19-3

    References

    • WO2008/130853 A1, ; Page/Page column 26-27 ; WO 2008/130853 A1

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   37.3
  • LogP   2.76414
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   1

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