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CS-W001157 4
Total: USD 88.00

2-Iodo-4-methoxyaniline

  • CAS No. 191348-14-8

  • Cat. No. CS-W004878
  • Purity≥95%
  • MDL No.MFCD07776739

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

2-Iodo-4-methoxyaniline|CS-W004878

Structure of 191348-14-8

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General Information

  • CAS No. 191348-14-8
  • Cat. No. CS-W004878
  • Purity ≥95%
  • MDL No. MFCD07776739
  • Storage -20°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₈INO
  • Molecular Weight 249.05
  • Synonym(s) 2-Iodo-4-methoxyphenylamine
  • SMILES NC1=CC=C(OC)C=C1I

Description

2-Iodo-4-methoxyaniline serves as a key intermediate in the synthesis of functionalized aromatic systems, featuring a reactive iodine handle and a methoxy group that enhances electron density. This combination enables efficient coupling reactions under mild conditions, particularly in palladium-catalyzed cross-couplings. The compound exhibits good stability and solubility in common organic solvents, facilitating straightforward handling in process development workflows.

Application

2-Iodo-4-methoxyaniline serves as a versatile building block in cross-coupling reactions, enabling efficient access to substituted anilines and biaryl scaffolds. Its iodine functionality provides high reactivity in Pd-catalyzed couplings, while the methoxy group offers moderate electron-donating character and stability under standard reaction conditions. The compound exhibits good bench stability and is readily purified by chromatography or recrystallization, making it well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • Tert-butyl (2-iodo-4-methoxyphenyl)carbamate|CS-0328638
      157496-75-8
    • ~88%
    • In-stock
      2-Iodo-4-methoxyaniline|CS-W004878
      191348-14-8

    References

    • Lizos, Dimitrios E.; Murphy, John A. Organic and Biomolecular Chemistry, 2003 , vol. 1, # 1 p. 117 - 122
  • Route2
    • null|null
      104-94-9
    • ~%
    • In-stock
      2-Iodo-4-methoxyaniline|CS-W004878
      191348-14-8

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 23, # 5 p. 1351 - 1357
  • Route3
    • 4-Amino-3-iodophenol|CS-0317408
      66416-73-7
    • null|null
      74-88-4
    • ~%
    • In-stock
      2-Iodo-4-methoxyaniline|CS-W004878
      191348-14-8

    References

    • Journal of Organic Chemistry, , vol. 67, # 18 p. 6395 - 6405

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07,GHS08
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335-H351-H361
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   35.25
  • LogP   1.882
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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