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CS-W001157 4
Total: USD 88.00

2,6-Dimethyl-4-nitroaniline

  • CAS No. 16947-63-0

  • Cat. No. CS-0054335
  • Purity≥97%
  • MDL No.None

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

2,6-Dimethyl-4-nitroaniline|CS-0054335

Structure of 16947-63-0

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General Information

  • CAS No. 16947-63-0
  • Cat. No. CS-0054335
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₀N₂O₂
  • Molecular Weight 166.18
  • Synonym(s) 4-NITRO-2,6-XYLIDINE
  • SMILES CC1=CC(=CC(C)=C1N)[N+]([O-])=O

Description

2,6-Dimethyl-4-nitroaniline features a nitro group flanked by two methyl substituents at the 2 and 6 positions, enhancing electron deficiency at the para site. This configuration promotes stability under standard conditions while enabling selective reactivity in electrophilic substitution and coupling reactions. The molecule integrates readily into functionalized aromatic scaffolds used in agrochemical and pharmaceutical synthesis.

Application

2,6-Dimethyl-4-nitroaniline serves as a valuable intermediate in the synthesis of functionalized heterocycles and pharmaceutical building blocks. Its electron-deficient aromatic ring enables efficient electrophilic substitution and facilitates coupling reactions under standard conditions. The ortho-methyl groups provide steric protection to the nitro group, enhancing stability during storage and handling. This compound functions effectively in reductive transformations and serves as a key scaffold for constructing nitrogen-containing APIs through established synthetic pathways.

Synthesis

  • Route1
    • N-(4-Amino-2,6-dimethylphenyl)acetamide|CS-0229906
      116296-36-7
    • ~97%
    • In-stock
      2,6-Dimethyl-4-nitroaniline|CS-0054335
      16947-63-0

    References

    • H. LUNDBECK A/S Patent: WO2006/29623 A1, 2006 ; Location in patent: Page/Page column 55 ; WO 2006/029623 A1
  • Route2
    • null|null
      67083-22-1
    • ~85%
    • In-stock
      2,6-Dimethyl-4-nitroaniline|CS-0054335
      16947-63-0

    References

    • Moorthy, Jarugu Narasimha; Saha, Satajit European Journal of Organic Chemistry, 2009 , # 5 p. 739 - 748
  • Route3
    • In-stock
      1-Methyl-3,5-dinitro-1,2-dihydropyridin-2-one|CS-W013205
      14150-94-8
    • null|null
      96-22-0
    • ~47%
    • In-stock
      2,6-Dimethyl-4-nitroaniline|CS-0054335
      16947-63-0
    • null|null
      68541-85-5

    References

    • Bulletin of the Chemical Society of Japan, , vol. 63, # 10 p. 2820 - 2827

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   69.16
  • LogP   1.79384
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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