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2-Hydroxy-5-(hydroxymethyl)benzaldehyde

  • CAS No. 74901-08-9

  • Cat. No. CS-0102097
  • Purity≥95%
  • MDL No.MFCD00456941

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

2-Hydroxy-5-(hydroxymethyl)benzaldehyde|CS-0102097

Structure of 74901-08-9

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General Information

  • CAS No. 74901-08-9
  • Cat. No. CS-0102097
  • Purity ≥95%
  • MDL No. MFCD00456941
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₈O₃
  • Molecular Weight 152.15
  • Synonym(s) 5-(Hydroxymethyl)salicylaldehyde
  • SMILES O=CC1=CC(CO)=CC=C1O

Description

2-Hydroxy-5-(hydroxymethyl)benzaldehyde features a strategically positioned aldehyde group flanked by two hydroxyl functionalities, enabling direct participation in condensation and oxidation reactions. This ortho-hydroxy aldehyde motif enhances reactivity in synthetic pathways requiring controlled electrophilicity and chelation potential. The molecule exhibits favorable solubility in polar solvents and stability under standard bench conditions, facilitating its use in the synthesis of complex heterocycles and bioactive scaffolds.

Application

2-Hydroxy-5-(hydroxymethyl)benzaldehyde serves as a versatile building block in synthetic organic chemistry, enabling the construction of bioactive heterocycles and natural product scaffolds. Its ortho-hydroxy and aldehyde functionalities facilitate efficient cyclizations, while the hydroxymethyl group offers sites for derivatization or oxidation to carboxylic acid. The compound exhibits good bench stability and is compatible with standard protecting group strategies, making it valuable for iterative synthesis workflows.

Synthesis

  • Route1
    • null|null
      90-02-8
    • ~%
    • In-stock
      2-Hydroxy-5-(hydroxymethyl)benzaldehyde|CS-0102097
      74901-08-9

    References

    • Stoermer; Behn Chemische Berichte, 1901 , vol. 34, p. 2459
  • Route2
    • null|null
      287398-51-0
    • ~85%
    • In-stock
      2-Hydroxy-5-(hydroxymethyl)benzaldehyde|CS-0102097
      74901-08-9

    References

    • Cho, Young Jin; Lee, Seung Hwan; Bae, Jong Woo; Pyun, Hyung-Jung; Yoon, Cheol Min Tetrahedron Letters, 2000 , vol. 41, # 20 p. 3915 - 3917
  • Route3

    References

    • Frederick, Raphael; Robert, Severine; Charlier, Caroline; De Ruyck, Jerome; Wouters, Johan; Pirotte, Bernard; Masereel, Bernard; Pochet, Lionel Journal of Medicinal Chemistry, 2005 , vol. 48, # 24 p. 7592 - 7603 Title/Abstract View citing articles Show Details Frederick, Raphael; Charlier, Caroline; Robert, Severine; Wouters, Johan; Masereel, Bernard; Pochet, Lionel Bioorganic and Medicinal Chemistry Letters, 2006 , vol. 16, # 7 p. 2017 - 2021

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   57.53
  • LogP   0.697
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   2

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