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CS-W001157 4
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N-(2-Formylphenyl)acetamide

  • CAS No. 13493-47-5

  • Cat. No. CS-0197889
  • Purity≥98%
  • MDL No.MFCD06739581

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

N-(2-Formylphenyl)acetamide|CS-0197889

Structure of 13493-47-5

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General Information

  • CAS No. 13493-47-5
  • Cat. No. CS-0197889
  • Purity ≥98%
  • MDL No. MFCD06739581
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₉NO₂
  • Molecular Weight 163.17
  • Synonym(s) 2-Acetamidobenzaldehyde
  • SMILES CC(NC1=CC=CC=C1C=O)=O

Description

N-(2-Formylphenyl)acetamide features a strategically positioned formyl group ortho to the amide linkage, enabling direct participation in cyclization reactions. This arrangement facilitates rapid access to functionalized benzimidazoles under mild conditions. The compound exhibits excellent solubility in common organic solvents and maintains stability during standard bench handling.

Application

N-(2-Formylphenyl)acetamide serves as a versatile building block in medicinal chemistry, enabling efficient access to benzimidazole and benzoxazole scaffolds via cyclization reactions. The ortho-formyl group facilitates directed metalation and acts as a key electrophilic handle for nucleophilic addition, while the acetamide moiety provides moderate stability and favorable solubility. Its bench-stable nature and compatibility with standard coupling and functionalization protocols make it well-suited for multi-step synthesis workflows.

Synthesis

  • Route1
    • In-stock
      2-Aminobenzaldehyde|CS-W007486
      529-23-7
    • null|null
      75-36-5
    • ~71%
    • In-stock
      N-(2-Formylphenyl)acetamide|CS-0197889
      13493-47-5

    References

    • STERIX LIMITED Patent: WO2009/66072 A2, 2009 ; Location in patent: Page/Page column 55; 58 ; WO 2009/066072 A2
  • Route2

    References

    • Matano, Yoshihiro; Nomura, Hazumi Angewandte Chemie - International Edition, 2002 , vol. 41, # 16 p. 3028 - 3031
  • Route3

    References

    • Quattropani, Anna; Dorbais, Jerome; Covini, David; Pittet, Pierre-Andre; Colovray, Veronique; Thomas, Russell J.; Coxhead, Richard; Halazy, Serge; Scheer, Alexander; Missotten, Marc; Ayala, Guidon; Bradshaw, Charles; De Raemy-Schenk, Anne-Marie; Nichols, Anthony; Cirillo, Rocco; Tos, Enrico Gillio; Giachetti, Claudio; Golzio, Lucia; Marinelli, Paolo; Church, Dennis J.; Barberis, Claude; Chollet, Andre; Schwarz, Matthias K. Journal of Medicinal Chemistry, 2005 , vol. 48, # 24 p. 7882 - 7905

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

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Computational Chemistry Data

  • TPSA   46.17
  • LogP   1.4575
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   2

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