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CS-W001157 4
Total: USD 88.00

2-Bromo-3,4-dimethoxybenzaldehyde

  • CAS No. 55171-60-3

  • Cat. No. CS-0179631
  • Purity≥98%
  • MDL No.MFCD07772896

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

2-Bromo-3,4-dimethoxybenzaldehyde|CS-0179631

Structure of 55171-60-3

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General Information

  • CAS No. 55171-60-3
  • Cat. No. CS-0179631
  • Purity ≥98%
  • MDL No. MFCD07772896
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₉BrO₃
  • Molecular Weight 245.07
  • Synonym(s) 2-Bromoveratraldehyde
  • SMILES O=CC1=CC=C(OC)C(OC)=C1Br

Description

2-Bromo-3,4-dimethoxybenzaldehyde features a brominated aromatic ring flanked by two methoxy groups and a formyl moiety, enabling selective coupling reactions. This electron-rich scaffold supports efficient derivatization in synthetic organic chemistry, particularly in cross-coupling and heterocycle formation under standard conditions.

Application

2-Bromo-3,4-dimethoxybenzaldehyde serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling efficient access to substituted benzimidazoles, heterocyclic scaffolds, and bioactive compounds via Pd-catalyzed cross-coupling. Its ortho-bromo and aldehyde functionalities offer complementary reactivity for sequential transformations, while the dimethoxy substitution enhances electron density and stability under standard reaction conditions.

Synthesis

  • Route1
    • In-stock
      2-Bromo-3-hydroxy-4-methoxybenzaldehyde|CS-W012954
      2973-58-2
    • null|null
      77-78-1
    • ~93%
    • In-stock
      2-Bromo-3,4-dimethoxybenzaldehyde|CS-0179631
      55171-60-3

    References

    • Sinhababu, Achintya K.; Borchardt, Ronald T. Journal of Organic Chemistry, 1983 , vol. 48, # 14 p. 2356 - 2360
  • Route2
    • In-stock
      2-Bromo-3-hydroxy-4-methoxybenzaldehyde|CS-W012954
      2973-58-2
    • null|null
      74-88-4
    • ~96%
    • In-stock
      2-Bromo-3,4-dimethoxybenzaldehyde|CS-0179631
      55171-60-3

    References

    • Wiegand; Schafer Tetrahedron, 1995 , vol. 51, # 18 p. 5341 - 5350
  • Route3
    • 2-Bromo-4-hydroxy-3-methoxybenzaldehyde|CS-0873376
      89984-24-7
    • null|null
      77-78-1
    • ~23%
    • In-stock
      2-Bromo-3,4-dimethoxybenzaldehyde|CS-0179631
      55171-60-3

    References

    • Burger, Adrian P. N.; Brandt, Edward V.; Roux, David G. Phytochemistry (Elsevier), 1983 , vol. 22, # 12 p. 2813 - 2818

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   35.53
  • LogP   2.2788
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   3

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