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CS-W001157 4
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2-Iodo-5-methylaniline

  • CAS No. 13194-69-9

  • Cat. No. CS-W004939
  • Purity≥97%
  • MDL No.MFCD00833395

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

2-Iodo-5-methylaniline|CS-W004939

Structure of 13194-69-9

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General Information

  • CAS No. 13194-69-9
  • Cat. No. CS-W004939
  • Purity ≥97%
  • MDL No. MFCD00833395
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₈IN
  • Molecular Weight 233.05
  • Synonym(s) 3-Amino-4-iodotoluene
  • SMILES NC1=CC(C)=CC=C1I

Description

2-Iodo-5-methylaniline features a methylaniline scaffold with iodine substitution at the ortho position, delivering enhanced reactivity in cross-coupling transformations. The electron-donating methyl group stabilizes the aromatic ring and improves solubility in polar organic media. This bench-stable compound serves as a direct precursor for functionalized anilines in medicinal chemistry and materials synthesis.

Application

2-Iodo-5-methylaniline serves as a versatile building block in medicinal chemistry and materials science, enabling palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig couplings. Its iodine substituent offers high reactivity under standard conditions, while the ortho-methyl group enhances stability and modulates electronic properties. The molecule exhibits excellent bench stability, facilitates straightforward purification, and functions reliably in the construction of biaryl scaffolds and functionalized heterocycles.

Synthesis

  • Route1
    • null|null
      108-44-1
    • ~63%
    • In-stock
      2-Iodo-5-methylaniline|CS-W004939
      13194-69-9

    References

    • Molecules, , vol. 7, # 12 p. 867 - 870
  • Route2

    References

    • Angewandte Chemie - International Edition, , vol. 50, # 32 p. 7354 - 7358
  • Route3
    • null|null
      89-62-3
    • ~%
    • In-stock
      2-Iodo-5-methylaniline|CS-W004939
      13194-69-9

    References

    • Chemische Berichte, , vol. 39, p. 269

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   26.02
  • LogP   2.18182
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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