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CS-W001157 4
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2-Bromo-6-hydroxybenzaldehyde

  • CAS No. 22532-61-2

  • Cat. No. CS-W001122
  • Purity≥98%
  • MDL No.MFCD08234722

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

2-Bromo-6-hydroxybenzaldehyde|CS-W001122

Structure of 22532-61-2

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General Information

  • CAS No. 22532-61-2
  • Cat. No. CS-W001122
  • Purity ≥98%
  • MDL No. MFCD08234722
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅BrO₂
  • Molecular Weight 201.02
  • Synonym(s) Salicylaldehyde,6-bromo- (8CI)
  • SMILES O=Cc1c(O)cccc1Br

Description

2-Bromo-6-hydroxybenzaldehyde features a bromine atom at the ortho position relative to the aldehyde, paired with a hydroxyl group at the para position, creating a uniquely activated aromatic scaffold. This combination enables direct functionalization in cross-coupling and oxidation reactions, while the phenolic OH enhances solubility and facilitates chelation in catalytic systems. The molecule exhibits robust stability under standard bench conditions, allowing straightforward handling in synthetic workflows.

Application

2-Bromo-6-hydroxybenzaldehyde serves as a versatile building block in synthetic organic chemistry, enabling direct functionalization at the aromatic ring and aldehyde site. Its bromo group facilitates palladium-catalyzed cross-coupling reactions, while the hydroxyl and aldehyde functionalities offer orthogonal handles for derivatization. The compound exhibits good bench stability and is compatible with standard protecting group strategies, making it valuable for constructing complex heterocyclic scaffolds and pharmaceutical intermediates.

Synthesis

  • Route1

    References

    • Rawat, Manish; Prutyanov, Victor; Wulff, William D. Journal of the American Chemical Society, 2006 , vol. 128, # 34 p. 11044 - 11053
  • Route2
    • null|null
      67-66-3
    • null|null
      591-20-8
    • ~33%
    • In-stock
      2-Bromo-6-hydroxybenzaldehyde|CS-W001122
      22532-61-2

    References

    • N.V. ORGANON Patent: WO2009/37220 A1, 2009 ; Location in patent: Page/Page column 134-135 ; WO 2009/037220 A1
  • Route3
    • Carbamic acid, N,N-diethyl-, 3-bromophenyl ester|CS-0191577
      863870-72-8
    • null|null
      68-12-2
    • ~58%
    • In-stock
      2-Bromo-6-hydroxybenzaldehyde|CS-W001122
      22532-61-2

    References

    • Wzorek, Joseph S.; Knoepfel, Thomas F.; Sapountzis, Ioannis; Evans, David A. Organic Letters, 2012 , vol. 14, # 23 p. 5840 - 5843

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

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Computational Chemistry Data

  • TPSA   37.3
  • LogP   1.9672
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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