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CS-W001157 4
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2-Amino-6-iodotoluene

  • CAS No. 172681-47-9

  • Cat. No. CS-W006233
  • Purity≥97%
  • MDL No.MFCD08062502

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

2-Amino-6-iodotoluene|CS-W006233

Structure of 172681-47-9

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General Information

  • CAS No. 172681-47-9
  • Cat. No. CS-W006233
  • Purity ≥97%
  • MDL No. MFCD08062502
  • 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-Iodo-2-mthylanilin
  • SMILES CC1=C(N)C=CC=C1I

Description

2-Amino-6-iodotoluene features a para-substituted aryl iodide paired with an ortho-amino group, enabling direct cross-coupling in palladium-catalyzed reactions. The electron-donating amino moiety enhances reactivity while maintaining stability under standard conditions. This bifunctional scaffold facilitates rapid access to complex heterocycles and functionalized arenes in medicinal chemistry and materials science applications.

Application

2-Amino-6-iodotoluene serves as a versatile building block in cross-coupling chemistry, enabling efficient access to substituted aromatic scaffolds. The ortho-iodo group facilitates palladium-catalyzed coupling reactions with broad functional group tolerance, while the amino functionality provides a handle for further derivatization or protection. Its bench-stable nature and compatibility with standard synthetic workflows make it a practical choice for medicinal chemistry and process development.

Synthesis

  • Route1

    References

    • Boulouard, Michel; Schumann-Bard, Pascale; Butt-Gueulle, Sabrina; Lohou, Elodie; Stiebing, Silvia; Collot, Valerie; Rault, Sylvain Bioorganic and Medicinal Chemistry Letters, 2007 , vol. 17, # 11 p. 3177 - 3180
  • Route2

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 17, # 11 p. 3177 - 3180
  • Route3
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      606-20-2
    • ~%
    • In-stock
      2-Amino-6-iodotoluene|CS-W006233
      172681-47-9

    References

    • Chemische Berichte, , vol. 37, p. 1021

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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