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CS-W001157 4
Total: USD 88.00

1,4-Benzodioxan-6-carboxaldehyde

  • CAS No. 29668-44-8

  • Cat. No. CS-D1456
  • Purity≥98%
  • MDL No.MFCD00010092

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

1,4-Benzodioxan-6-carboxaldehyde|CS-D1456

Structure of 29668-44-8

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General Information

  • CAS No. 29668-44-8
  • Cat. No. CS-D1456
  • Purity ≥98%
  • MDL No. MFCD00010092
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₈O₃
  • Molecular Weight 164.16
  • Synonym(s) 1,4-Benzodioxane-6-aldehyde; 1,4-Benzodioxane-6-carboxaldehyde; 2,3-Dihydro-1,4-benzodioxan-6-carboxaldehyde; 6-Formyl-1,4-benzodioxane
  • SMILES [H]C(C1=CC=C(OCCO2)C2=C1)=O

Description

1,4-Benzodioxan-6-carboxaldehyde features a rigid, electron-rich benzodioxane core with a strategically positioned aldehyde group. This moiety enables direct coupling in heterocyclic synthesis and serves as a key scaffold for bioactive molecule development. The compound exhibits excellent stability under standard conditions and integrates readily into complex molecular architectures.

Application

1,4-Benzodioxan-6-carboxaldehyde serves as a versatile scaffold for medicinal chemistry and materials science, enabling efficient access to bioactive heterocycles. Its aldehyde functionality facilitates reductive amination, Wittig reactions, and coupling with nucleophiles under mild conditions. The rigid, electron-rich benzodioxane core enhances metabolic stability and modulates lipophilicity, making it valuable in lead optimization. Bench-stable and amenable to standard purification methods, it functions reliably in multi-step syntheses.

Synthesis

  • Route1
    • null|null
      106-93-4
    • In-stock
      Protocatechualdehyde|CS-W009195
      139-85-5
    • ~97%
    • In-stock
      1,4-Benzodioxan-6-carboxaldehyde|CS-D1456
      29668-44-8

    References

    • UNIBIOSCREEN S.A. Patent: WO2005/105753 A2, 2005 ; Location in patent: Page/Page column 63-64 ; WO 2005/105753 A2
  • Route2
    • null|null
      82102-37-2
    • In-stock
      6-Bromo-2,3-dihydrobenzo[b][1,4]dioxine|CS-W002191
      52287-51-1
    • ~78%
    • In-stock
      1,4-Benzodioxan-6-carboxaldehyde|CS-D1456
      29668-44-8

    References

    • Korsager, Signe; Taaning, Rolf H.; Lindhardt, Anders T.; Skrydstrup, Troels Journal of Organic Chemistry, 2013 , vol. 78, # 12 p. 6112 - 6120
  • Route3
    • In-stock
      2,3-Dihydrobenzo[b][1,4]dioxine|CS-W017762
      493-09-4
    • null|null
      100-97-0
    • ~73%
    • In-stock
      1,4-Benzodioxan-6-carboxaldehyde|CS-D1456
      29668-44-8

    References

    • Zhilina, Z. I.; Mel'nik, V. I.; Andronati, S. A.; Abramovich, A. E. Journal of Organic Chemistry USSR (English Translation), 1989 , vol. 25, # 5.2 p. 957 - 963 Zhurnal Organicheskoi Khimii, 1989 , vol. 25, # 5 p. 1063 - 1070

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   35.53
  • LogP   1.2703
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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