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CS-W001157 4
Total: USD 88.00

2-Chloro-3-hydroxy-4-methoxybenzaldehyde

  • CAS No. 37687-57-3

  • Cat. No. CS-0012609
  • Purity≥95%
  • MDL No.MFCD03425852

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

2-Chloro-3-hydroxy-4-methoxybenzaldehyde|CS-0012609

Structure of 37687-57-3

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General Information

  • CAS No. 37687-57-3
  • Cat. No. CS-0012609
  • Purity ≥95%
  • MDL No. MFCD03425852
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇ClO₃
  • Molecular Weight 186.59
  • Synonym(s) Chloroisovaniline
  • SMILES O=CC1=CC=C(OC)C(O)=C1Cl

Description

2-Chloro-3-hydroxy-4-methoxybenzaldehyde features a strategically positioned aldehyde group flanked by electron-donating methoxy and hydroxyl substituents, enabling efficient coupling in cross-coupling and condensation reactions. The chloro group provides a handle for further functionalization, while the phenolic hydroxyl enhances solubility and reactivity in polar media.

Application

2-Chloro-3-hydroxy-4-methoxybenzaldehyde serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling efficient access to substituted benzimidazoles, quinolines, and other heterocyclic scaffolds. The ortho-chloro and meta-hydroxy functionalities facilitate electrophilic substitution and directed metalation, while the aldehyde group supports reductive amination, imine formation, and Ullmann-type coupling reactions. Bench-stable and amenable to standard purification methods, it functions effectively in multi-step syntheses requiring functional group compatibility and predictable reactivity.

Synthesis

  • Route1

    References

    • Weinstock; Ladd; Wilson; Brush; Yim; Gallagher Jr.; McCarthy; Silvestri; Sarau; Flaim Journal of Medicinal Chemistry, 1986 , vol. 29, # 11 p. 2315 - 2325
  • Route2

    References

    • Hornbaker; Burger Journal of the American Chemical Society, 1955 , vol. 77, p. 5314,5317
  • Route3
    • 2-chloro-1-(chloromethyl)-3,4-dimethoxybenzene|CS-0061980
      93983-14-3
    • ~%
    • In-stock
      2-Chloro-3-hydroxy-4-methoxybenzaldehyde|CS-0012609
      37687-57-3

    References

    • Hornbaker; Burger Journal of the American Chemical Society, 1955 , vol. 77, p. 5314,5317

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-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   46.53
  • LogP   1.8667
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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