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CS-W001157 4
Total: USD 88.00

2-Iodo-4-methoxybenzoic acid

  • CAS No. 54435-09-5

  • Cat. No. CS-W005751
  • Purity≥95%
  • MDL No.MFCD09909619

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

2-Iodo-4-methoxybenzoic acid|CS-W005751

Structure of 54435-09-5

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General Information

  • CAS No. 54435-09-5
  • Cat. No. CS-W005751
  • Purity ≥95%
  • MDL No. MFCD09909619
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇IO₃
  • Molecular Weight 278.04
  • Synonym(s) Benzoic acid,2-iodo-4-methoxy
  • SMILES COC1=CC(I)=C(C=C1)C(O)=O

Description

2-Iodo-4-methoxybenzoic acid features a reactive iodine atom at the ortho position relative to a carboxylic acid group, paired with a para-methoxy substituent that enhances electron density. This combination enables efficient cross-coupling reactions in late-stage functionalization, particularly under palladium catalysis. The molecule exhibits good stability under standard bench conditions and facilitates direct incorporation into complex molecular architectures without requiring protective group manipulations.

Application

2-Iodo-4-methoxybenzoic acid serves as a versatile building block for Suzuki-Miyaura and Stille coupling reactions, enabling the construction of biaryl and heteroaryl scaffolds under standard catalytic conditions. The iodide group exhibits high reactivity with palladium catalysts, while the carboxylic acid and methoxy functionalities provide orthogonal handles for further derivatization. Bench-stable and readily purified by recrystallization, it facilitates efficient access to functionalized aromatic systems in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Koizumi,J. et al. Chemical and Pharmaceutical Bulletin, 1964 , vol. 12, # 6 p. 696 - 705
  • Route2

    References

    • Liang, Pi-Hui; Hsin, Ling-Wei; Pong, Sung-Ling; Hsu, Chia-Huei; Cheng, Chen-Yu Journal of the Chinese Chemical Society, 2003 , vol. 50, # 3 A p. 449 - 456
  • Route3
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      7664-93-9
    • In-stock
      2-Amino-4-methoxybenzoic acid|CS-B0778
      4294-95-5
    • ~%
    • In-stock
      2-Iodo-4-methoxybenzoic acid|CS-W005751
      54435-09-5

    References

    • Sterling Winthrop Inc. Patent: US5614530 A1, 1997 ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 3439
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H302+H312-H315-H319-H331-H335
Precautionary Statements : P264-P270-P330-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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