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CS-W001157 4
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5-Hydroxy-benzene-1,3-dicarbaldehyde

  • CAS No. 144876-14-2

  • Cat. No. CS-0110475
  • Purity≥98%
  • MDL No.MFCD13192816

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

5-Hydroxy-benzene-1,3-dicarbaldehyde|CS-0110475

Structure of 144876-14-2

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General Information

  • CAS No. 144876-14-2
  • Cat. No. CS-0110475
  • Purity ≥98%
  • MDL No. MFCD13192816
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆O₃
  • Molecular Weight 150.13
  • Synonym(s) 5-hydroxybenzene-1,3-dicarbaldehyde
  • SMILES O=CC1=CC(O)=CC(C=O)=C1

Description

5-Hydroxy-benzene-1,3-dicarbaldehyde features two aldehyde groups flanking a hydroxyl-bearing aromatic ring, enabling selective coupling in multistep syntheses. The electron-rich phenolic moiety enhances reactivity in nucleophilic additions, while the para-oriented hydroxyl stabilizes intermediates through intramolecular hydrogen bonding. This structure supports efficient integration into complex molecular architectures under standard conditions.

Application

5-Hydroxy-benzene-1,3-dicarbaldehyde serves as a versatile bifunctional building block for the synthesis of complex heterocycles and bioactive scaffolds. Its ortho-dialdehyde motif enables efficient condensation reactions with amines and hydrazides, facilitating the construction of imidazoles, triazines, and other nitrogen-containing rings. The phenolic hydroxyl group provides additional sites for derivatization or metal coordination, enhancing utility in ligand design and molecular scaffold development. Bench-stable and amenable to standard purification methods, it functions reliably in multi-step synthetic sequences.

Synthesis

  • Route1
    • (5-Hydroxy-1,3-phenylene)dimethanol|CS-0539970
      153707-56-3
    • ~62%
    • In-stock
      5-Hydroxy-benzene-1,3-dicarbaldehyde|CS-0110475
      144876-14-2

    References

    • Servin, Paul; Rebout, Cyrille; Laurent, Regis; Peruzzini, Maurizio; Caminade, Anne-Marie; Majoral, Jean-Pierre Tetrahedron Letters, 2007 , vol. 48, # 4 p. 579 - 583
  • Route2
    • Diethyl 5-hydroxyisophthalate|CS-0151778
      39630-68-7
    • ~%
    • In-stock
      5-Hydroxy-benzene-1,3-dicarbaldehyde|CS-0110475
      144876-14-2

    References

    • Star, Alexander; Liu, Yi; Grant, Kevin; Ridvan, Ludek; Stoddart, J. Fraser; Steuerman, David W.; Diehl, Michael R.; Boukai, Akram; Heath, James R. Macromolecules, 2003 , vol. 36, # 3 p. 553 - 560
  • Route3

    References

    • Provent, Christophe; Chautemps, Pierre; Gellon, Gisele; Pierre, Jean-Louis Tetrahedron Letters, 1996 , vol. 37, # 9 p. 1393 - 1396

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362+P364

Quality Control

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Computational Chemistry Data

  • TPSA   54.37
  • LogP   1.0172
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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