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CS-W001157 4
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4-(Tetrahydropyran-4-yloxy)benzaldehyde

  • CAS No. 215460-40-5

  • Cat. No. CS-0205617
  • Purity≥98%
  • MDL No.MFCD09064964

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

4-(Tetrahydropyran-4-yloxy)benzaldehyde|CS-0205617

Structure of 215460-40-5

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General Information

  • CAS No. 215460-40-5
  • Cat. No. CS-0205617
  • Purity ≥98%
  • MDL No. MFCD09064964
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₄O₃
  • Molecular Weight 206.24
  • Synonym(s) None
  • SMILES C1=C(C=CC(=C1)OC2CCOCC2)C=O

Description

4-(Tetrahydropyran-4-yloxy)benzaldehyde features a protected aliphatic hydroxyl group paired with an aromatic aldehyde, enabling stable handling and selective deprotection under mild acidic conditions. This combination supports efficient synthetic routing in complex molecule assembly, particularly in carbohydrate-derived architectures and functionalized arenes where orthogonal reactivity is essential.

Application

4-(Tetrahydropyran-4-yloxy)benzaldehyde serves as a robust protecting group strategy for phenolic alcohols, enabling selective transformations in complex molecule synthesis. The tetrahydropyranyl ether functionality provides excellent stability under acidic and basic conditions while allowing orthogonal deprotection with mild acid. Its benzaldehyde handle facilitates further functionalization via nucleophilic addition or Wittig-type reactions, making it a practical building block for pharmaceutical intermediates and functionalized aromatic scaffolds.

Synthesis

  • Route1

    References

    • Duplantier, Allen J.; Efremov, Ivan; Candler, John; Doran, Angela C.; Ganong, Alan H.; Haas, Jessica A.; Hanks, Ashley N.; Kraus, Kenneth G.; Lazzaro Jr., John T.; Lu, Jiemin; Maklad, Noha; McCarthy, Sheryl A.; O'Sullivan, Theresa J.; Rogers, Bruce N.; Siuciak, Judith A.; Spracklin, Douglas K.; Zhang, Lei Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 9 p. 2524 - 2529

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   2.0569
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   3

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