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CS-W001157 4
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4-Methoxy-2,6-dimethylaniline

  • CAS No. 34743-49-2

  • Cat. No. CS-W005568
  • Purity≥98%
  • MDL No.MFCD03792670

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

4-Methoxy-2,6-dimethylaniline|CS-W005568

Structure of 34743-49-2

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General Information

  • CAS No. 34743-49-2
  • Cat. No. CS-W005568
  • Purity ≥98%
  • MDL No. MFCD03792670
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₃NO
  • Molecular Weight 151.21
  • Synonym(s) 4-methoxy-2,6-dimethyl-aniline
  • SMILES COC1=CC(C)=C(N)C(C)=C1

Description

4-Methoxy-2,6-dimethylaniline features a methoxy group at the para position and two methyl substituents flanking the amino nitrogen, delivering enhanced electron density and steric protection. This combination imparts improved stability and solubility in organic solvents, facilitating use in coupling reactions and as a building block for functional dyes and pharmaceutical intermediates.

Application

4-Methoxy-2,6-dimethylaniline serves as a valuable building block in medicinal chemistry and agrochemical synthesis, offering enhanced solubility and metabolic stability compared to unsubstituted anilines. Its ortho-methyl groups provide steric shielding, improving bench stability and reducing undesired side reactions. The molecule functions effectively in Pd-catalyzed cross-coupling reactions and serves as a key intermediate for heterocyclic scaffolds, particularly in the construction of substituted pyridines and benzimidazoles.

Synthesis

  • Route1

    References

    • JANSSEN PHARMACEUTICA N.V.; ARTS, Frank, Xavier, Jozef, Herwig Patent: WO2006/15985 A1, 2006 ; Location in patent: Page/Page column 55-56 ;
  • Route2
    • null|null
      153968-41-3
    • ~49%
    • In-stock
      4-Methoxy-2,6-dimethylaniline|CS-W005568
      34743-49-2

    References

    • Sprecher, Milon; Kost, Daniel Journal of the American Chemical Society, 1994 , vol. 116, # 3 p. 1016 - 1026
  • Route3
    • In-stock
      4-Amino-3,5-dimethylphenol|CS-W019281
      3096-70-6
    • null|null
      74-88-4
    • ~67%
    • In-stock
      4-Methoxy-2,6-dimethylaniline|CS-W005568
      34743-49-2

    References

    • Micksch, Maik; Tenne, Mario; Strassner, Thomas European Journal of Organic Chemistry, 2013 , # 27 p. 6137 - 6145

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   35.25
  • LogP   1.89424
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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