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CS-W001157 4
Total: USD 88.00

4-(Methylamino)benzaldehyde

  • CAS No. 556-21-8

  • Cat. No. CS-0527406
  • Purity≥97%
  • MDL No.None

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

4-(Methylamino)benzaldehyde|CS-0527406

Structure of 556-21-8

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General Information

  • CAS No. 556-21-8
  • Cat. No. CS-0527406
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₉NO
  • Molecular Weight 135.16
  • Synonym(s) 4-methylaminobenzaldehyde
  • SMILES O=CC1=CC=C(NC)C=C1

Description

4-(Methylamino)benzaldehyde is a bench-stable, electron-rich aromatic aldehyde featuring a para-methylamino group that enhances reactivity in nucleophilic addition and condensation reactions. This compound integrates readily into synthetic pathways for dyes, pharmaceutical intermediates, and ligand design due to its dual functional handles.

Application

4-(Methylamino)benzaldehyde serves as a versatile building block in synthetic organic chemistry, enabling efficient access to substituted anilines and heterocyclic scaffolds. Its aldehyde functionality facilitates imine formation, reductive amination, and Ullmann-type coupling reactions, while the methylamino group offers moderate nucleophilicity and compatibility with common protecting group strategies. The compound exhibits good bench stability and is readily purified by recrystallization or column chromatography, making it well-suited for iterative synthesis workflows in medicinal chemistry and process development.

Synthesis

  • Route1
    • (4-(Methylamino)phenyl)methanol|CS-0151031
      181819-75-0
    • ~47%
    • In-stock
      4-(Methylamino)benzaldehyde|CS-0527406
      556-21-8

    References

    • Iwasawa, Tetsuo; Mann, Enrique; Rebek Jr., Julius Journal of the American Chemical Society, 2006 , vol. 128, # 29 p. 9308 - 9309
  • Route2
    • In-stock
      4-Bromobenzaldehyde|CS-W001138
      1122-91-4
    • null|null
      74-89-5
    • ~87%
    • In-stock
      4-(Methylamino)benzaldehyde|CS-0527406
      556-21-8

    References

    • Jiao, Jiao; Zhang, Xi-Ru; Chang, Ning-Hui; Wang, Jie; Wei, Jun-Fa; Shi, Xian-Ying; Chen, Zhan-Guo Journal of Organic Chemistry, 2011 , vol. 76, # 4 p. 1180 - 1183
  • Route3

    References

    • Sorokin, Vladimir I.; Pozharskii, Alexander F.; Ozeryanskii, Valery A. Journal of Fluorine Chemistry, 2013 , vol. 154, p. 67 - 72

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-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P363-P501

Quality Control

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Computational Chemistry Data

  • TPSA   29.1
  • LogP   1.5408
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   2

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