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Methyl 5-bromo-2-formylbenzoate

  • CAS No. 1016163-89-5

  • Cat. No. CS-0103320
  • Purity≥96%
  • MDL No.MFCD16036575

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

Methyl 5-bromo-2-formylbenzoate|CS-0103320

Structure of 1016163-89-5

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General Information

  • CAS No. 1016163-89-5
  • Cat. No. CS-0103320
  • Purity ≥96%
  • MDL No. MFCD16036575
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₇BrO₃
  • Molecular Weight 243.05
  • Synonym(s) None
  • SMILES O=C(C1=CC(Br)=CC=C1C=O)OC

Description

Methyl 5-bromo-2-formylbenzoate features a formyl group at the ortho position relative to the ester, creating a highly reactive electrophilic site. The para-bromo substitution enhances electron-withdrawing character, stabilizing adjacent intermediates in cross-coupling reactions. This compound integrates readily into complex molecular architectures under mild conditions, offering precise control in synthetic sequences requiring directed functionalization.

Application

Methyl 5-bromo-2-formylbenzoate serves as a versatile building block in synthetic organic chemistry, enabling direct functionalization at the formyl and bromo positions. Its ortho-formyl group facilitates nucleophilic addition and condensation reactions, while the bromine atom supports palladium-catalyzed cross-couplings. The methyl ester is compatible with standard reduction and derivatization protocols, offering a stable, bench-ready platform for constructing complex heterocycles and pharmaceutical intermediates.

Synthesis

  • Route1

    References

    • Lartia, Remy; Allain, Clemence; Bordeau, Guillaume; Schmidt, Falk; Fiorini-Debuisschert, Celine; Charra, Fabrice; Teulade-Fichou, Marie-Paule Journal of Organic Chemistry, 2008 , vol. 73, # 5 p. 1732 - 1744
  • Route2
    • In-stock
      5-Bromo-2-formylbenzoic acid|CS-0029754
      4785-52-8
    • null|null
      74-88-4
    • ~%
    • In-stock
      Methyl 5-bromo-2-formylbenzoate|CS-0103320
      1016163-89-5

    References

    • Mirabdolbaghi, Roya; Dudding, Travis Tetrahedron, 2013 , vol. 69, # 15 p. 3287 - 3292
  • Route3
    • null|null
      1265286-99-4
    • ~95%
    • In-stock
      Methyl 5-bromo-2-formylbenzoate|CS-0103320
      1016163-89-5

    References

    • Herzog, Beat; Neier, Reinhard Arkivoc, 2011 , vol. 2011, # 6 p. 29 - 44

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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   43.37
  • LogP   2.0482
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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