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CS-W001157 4
Total: USD 88.00

2,4-Difluoro-6-hydroxybenzaldehyde

  • CAS No. 136516-64-8

  • Cat. No. CS-0027054
  • Purity≥96%
  • MDL No.MFCD03701048

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

2,4-Difluoro-6-hydroxybenzaldehyde|CS-0027054

Structure of 136516-64-8

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General Information

  • CAS No. 136516-64-8
  • Cat. No. CS-0027054
  • Purity ≥96%
  • MDL No. MFCD03701048
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄F₂O₂
  • Molecular Weight 158.10
  • Synonym(s) 4,6-Difluoro-2-hydroxybenzaldehyde
  • SMILES O=CC1=C(O)C=C(F)C=C1F

Description

2,4-Difluoro-6-hydroxybenzaldehyde features a uniquely reactive aldehyde group flanked by two fluorine atoms and a phenolic hydroxyl, enabling direct functionalization in late-stage synthesis. The electron-withdrawing fluorines enhance electrophilicity at the carbonyl carbon, while the ortho-hydroxy functionality supports chelation or intramolecular stabilization. This combination facilitates efficient coupling reactions under mild conditions, particularly in pharmaceutical intermediates and bioconjugation workflows.

Application

2,4-Difluoro-6-hydroxybenzaldehyde serves as a versatile building block in medicinal chemistry, enabling direct incorporation of fluorinated aromatic scaffolds with orthogonal functionality. The aldehyde group facilitates efficient imine formation and reductive amination, while the phenolic hydroxyl supports derivatization via etherification or esterification. Bench-stable and compatible with standard purification methods, it functions effectively in multi-step syntheses requiring controlled regioselectivity and functional group tolerance.

Synthesis

  • Route1
    • null|null
      50-00-0
    • In-stock
      3,5-Difluorophenol|CS-D1731
      2713-34-0
    • ~99%
    • In-stock
      2,4-Difluoro-6-hydroxybenzaldehyde|CS-0027054
      136516-64-8

    References

    • Wang, Shouming; Beck, Richard; Burd, Andrew; Blench, Toby; Marlin, Frederic; Ayele, Tenagne; Buxton, Stuart; Dagostin, Claudio; Malic, Maja; Joshi, Rina; Barry, John; Sajad, Mohammed; Cheung, Chiming; Shaikh, Shaheda; Chahwala, Suresh; Criandera, Chaman; Baumgartner, Christine; Holthoff, Hans-Peter; Murray, Elizabeth; Blackney, Michael; Giddings, Amanda Journal of Medicinal Chemistry, 2010 , vol. 53, # 4 p. 1473 - 1482
  • Route2
    • 2,4-Difluoro-6-methoxybenzaldehyde|CS-0465970
      608515-57-7
    • ~72%
    • In-stock
      2,4-Difluoro-6-hydroxybenzaldehyde|CS-0027054
      136516-64-8

    References

    • Merck Sharp and Dohme Limited Patent: WO2004/46133 A1, 2004 ; Location in patent: Page 24-25 ; WO 2004/046133 A1
  • Route3
    • null|null
      899427-17-9
    • ~%
    • In-stock
      2,4-Difluoro-6-hydroxybenzaldehyde|CS-0027054
      136516-64-8

    References

    • Synthesis, , # 10 p. 1575 - 1577

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   1.4829
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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