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CS-W001157 4
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4-Formyl-2-methoxybenzonitrile

  • CAS No. 21962-49-2

  • Cat. No. CS-0105523
  • Purity≥97%
  • MDL No.MFCD16295254

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

4-Formyl-2-methoxybenzonitrile|CS-0105523

Structure of 21962-49-2

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General Information

  • CAS No. 21962-49-2
  • Cat. No. CS-0105523
  • Purity ≥97%
  • MDL No. MFCD16295254
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₇NO₂
  • Molecular Weight 161.16
  • Synonym(s) 4-Cyano-3-methoxy-benzaldehyde
  • SMILES N#CC1=CC=C(C=O)C=C1OC

Description

4-Formyl-2-methoxybenzonitrile features a formyl group at the para position relative to a nitrile, flanked by a methoxy substituent ortho to the nitrile. This electron-deficient aromatic scaffold enables direct coupling in cross-coupling reactions and serves as a key building block for bioactive heterocycles and functionalized aryl systems under standard conditions.

Application

4-Formyl-2-methoxybenzonitrile serves as a versatile building block in medicinal chemistry and materials science, enabling efficient access to functionalized aromatic scaffolds. Its orthogonal functionality—formyl, methoxy, and nitrile groups—facilitates sequential transformations including reductive amination, nucleophilic addition, and Suzuki coupling. The compound exhibits excellent bench stability and is compatible with standard purification methods, making it well-suited for iterative synthesis workflows in API development and heterocycle construction.

Synthesis

  • Route1
    • null|null
      194018-68-3
    • ~57%
    • In-stock
      4-Formyl-2-methoxybenzonitrile|CS-0105523
      21962-49-2

    References

    • ENDORECHERCHE, INC. Patent: WO2005/66194 A1, 2005 ; Location in patent: Page/Page column 161 ; WO 2005/066194 A1
  • Route2
    • null|null
      557-21-1
    • null|null
      194018-68-3
    • ~%
    • In-stock
      4-Formyl-2-methoxybenzonitrile|CS-0105523
      21962-49-2

    References

    • MERCK SHARP and DOHME CORP.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong Patent: WO2013/28474 A1, 2013 ; Location in patent: Page/Page column 79 ;
  • Route3
    • Vanillin, ≥97%|CS-1268660
      121-33-5
    • ~%
    • In-stock
      4-Formyl-2-methoxybenzonitrile|CS-0105523
      21962-49-2

    References

    • MERCK SHARP and DOHME CORP.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong Patent: WO2013/28474 A1, 2013 ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 3439
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301+H311+H331-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   50.09
  • LogP   1.37938
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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