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CS-W001157 4
Total: USD 88.00

2,4,6-Trimethoxyaniline

  • CAS No. 14227-17-9

  • Cat. No. CS-W007291
  • Molecule weight183.20
  • Purity≥95%
  • MDL No.None

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

2,4,6-Trimethoxyaniline|CS-W007291

Structure of 14227-17-9

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General Information

  • CAS No. 14227-17-9
  • Cat. No. CS-W007291
  • Purity ≥95%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₃NO₃
  • Molecular Weight 183.20
  • Synonym(s) Benzenamine,2,4,6-trimethoxy
  • SMILES NC1=C(OC)C=C(OC)C=C1OC

Description

2,4,6-Trimethoxyaniline features three methoxy groups positioned ortho and para to the amino group, imparting significant electron-donating character and enhanced solubility in organic solvents. This derivative exhibits improved stability compared to unsubstituted anilines and serves as a key building block for functionalized dyes, agrochemical intermediates, and advanced polymer precursors.

Application

2,4,6-Trimethoxyaniline serves as a versatile building block in synthetic organic chemistry, enabling the construction of substituted anilines and heterocyclic scaffolds through standard coupling and cyclization reactions. Its three methoxy groups enhance solubility and modulate electronic properties, facilitating selective functionalization. The compound exhibits bench stability and ease of purification, making it well-suited for medicinal chemistry campaigns and process-scale synthesis.

Synthesis

  • Route1

    References

    • Knoelker, Hans-Joachim; Baum, Gerhard; Foitzik, Norbert; Goesmann, Helmut; Gonser, Peter; Jones, Peter G.; Roettele, Herbert European Journal of Inorganic Chemistry, 1998 , # 7 p. 993 - 1007
  • Route2
    • 2,4,6-Trimethoxybenzamide|CS-0512477
      17483-54-4
    • ~37%
    • In-stock
      2,4,6-Trimethoxyaniline|CS-W007291
      14227-17-9

    References

    • Barnes, Matthew J.; Burschka, Christian; Buettner, Matthias W.; Conroy, Richard; Daiss, Juergen O.; Gray, Ian C.; Hendrick, Alan G.; Tam; Kuehn, Diana; Miller, David J.; Mills, John S.; Mitchell, Philip; Montana, John G.; Muniandy, Parameswary A.; Rapley, Helen; Showell, Graham A.; Tebbe, David; Tacke, Reinhold; Warneck, Julie B.H.; Zhu, Bin ChemMedChem, 2011 , vol. 6, # 11 p. 2070 - 2080
  • Route3
    • null|null
      148678-90-4
    • ~99%
    • In-stock
      2,4,6-Trimethoxyaniline|CS-W007291
      14227-17-9

    References

    • Mitchell, Helen; Leblanc, Yves Journal of Organic Chemistry, 1994 , vol. 59, # 3 p. 682 - 687

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   53.71
  • LogP   1.2946
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   3

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