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CS-W001157 4
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2,3-Dimethoxyaniline

  • CAS No. 6299-67-8

  • Cat. No. CS-W016280
  • Purity≥96%
  • MDL No.MFCD00180769

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

2,3-Dimethoxyaniline|CS-W016280

Structure of 6299-67-8

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General Information

  • CAS No. 6299-67-8
  • Cat. No. CS-W016280
  • Purity ≥96%
  • MDL No. MFCD00180769
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₁NO₂
  • Molecular Weight 153.18
  • Synonym(s) Dimethoxyaniline
  • SMILES NC1=CC=CC(OC)=C1OC

Description

2,3-Dimethoxyaniline features two methoxy groups positioned ortho to the amino group, enhancing electron density and solubility in polar solvents. This configuration supports efficient coupling reactions in synthetic routes for dyes, pharmaceuticals, and functional materials. The compound exhibits improved stability under standard bench conditions compared to unsubstituted anilines.

Application

2,3-Dimethoxyaniline serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling direct incorporation of ortho-dimethoxyaryl motifs. Its stability under standard reaction conditions and tolerance to diverse functional groups facilitate efficient coupling reactions, including Suzuki-Miyaura and Buchwald-Hartwig protocols. The molecule functions as a key intermediate for heterocyclic scaffolds and provides access to bioactive analogs via controlled electrophilic substitution or metal-catalyzed transformations.

Synthesis

  • Route1
    • null|null
      153718-64-0
    • ~97%
    • In-stock
      2,3-Dimethoxyaniline|CS-W016280
      6299-67-8

    References

    • Fumagalli, Laura; Pallavicini, Marco; Budriesi, Roberta; Bolchi, Cristiano; Canovi, Mara; Chiarini, Alberto; Chiodini, Giuseppe; Gobbi, Marco; Laurino, Paola; Micucci, Matteo; Straniero, Valentina; Valoti, Ermanno Journal of Medicinal Chemistry, 2013 , vol. 56, # 16 p. 6402 - 6412
  • Route2

    References

    • Feldman, Ken S.; Coca, Adiel Tetrahedron Letters, 2008 , vol. 49, # 13 p. 2136 - 2138
  • Route3
    • 2,3-Dimethoxybenzamide|CS-0186489
      1521-39-7
    • ~47%
    • In-stock
      2,3-Dimethoxyaniline|CS-W016280
      6299-67-8

    References

    • Stuart; Khora; McKenney Jr.; Castle Journal of Heterocyclic Chemistry, 1987 , vol. 24, # 6 p. 1589 - 1594

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-H315-H319
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P501

Quality Control

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Computational Chemistry Data

  • TPSA   44.48
  • LogP   1.286
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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