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CS-W001157 4
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2-Iodo-5-methoxybenzoic acid

  • CAS No. 54413-93-3

  • Cat. No. CS-W005683
  • Purity≥95%
  • MDL No.None

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

2-Iodo-5-methoxybenzoic acid|CS-W005683

Structure of 54413-93-3

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General Information

  • CAS No. 54413-93-3
  • Cat. No. CS-W005683
  • Purity ≥95%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇IO₃
  • Molecular Weight 278.04
  • Synonym(s) None
  • SMILES O=C(O)C1=CC(OC)=CC=C1I

Description

2-Iodo-5-methoxybenzoic acid features a strategically positioned iodine atom and methoxy group on the aromatic ring, enabling efficient cross-coupling reactions. The carboxylic acid functionality provides direct handle for peptide conjugation or derivatization. This bench-stable compound integrates readily into synthetic sequences requiring halogen-directed functionalization.

Application

2-Iodo-5-methoxybenzoic acid serves as a versatile building block for Suzuki-Miyaura and other palladium-catalyzed cross-coupling reactions, enabling efficient access to substituted biaryls and functionalized heterocycles. The iodide group provides high reactivity under standard coupling conditions, while the methoxy and carboxylic acid functionalities offer orthogonal handles for further derivatization. Bench-stable and readily purified by recrystallization, it functions effectively in both academic and industrial synthetic workflows.

Synthesis

  • Route1

    References

    • Wu, Liang; Aliev, Abil E.; Caddick, Stephen; Fitzmaurice, Richard J.; Tocher, Derek A.; King, Frank D. Chemical Communications, 2010 , vol. 46, # 2 p. 318 - 320
  • Route2

    References

    • Hamamoto, Hiromi; Hattori, Sho; Takemaru, Kaori; Miki, Yasuyoshi Synlett, 2011 , # 11 p. 1563 - 1566
  • Route3
    • Ethyl 2-iodo-5-methoxybenzoate|CS-0376250
      104807-65-0
    • ~70%
    • In-stock
      2-Iodo-5-methoxybenzoic acid|CS-W005683
      54413-93-3

    References

    • Moss, Robert A.; Chatterjee, Swati; Wilk, Boguslawa Journal of Organic Chemistry, 1986 , vol. 51, # 22 p. 4303 - 4307

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   46.53
  • LogP   1.998
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   2

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