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CS-W001157 4
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5-Fluoro-2-iodobenzoic acid

  • CAS No. 52548-63-7

  • Cat. No. CS-W008430
  • Purity≥98%
  • MDL No.MFCD00837316

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

5-Fluoro-2-iodobenzoic acid|CS-W008430

Structure of 52548-63-7

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General Information

  • CAS No. 52548-63-7
  • Cat. No. CS-W008430
  • Purity ≥98%
  • MDL No. MFCD00837316
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄FIO₂
  • Molecular Weight 266.01
  • Synonym(s) benzoic acid, 5-fluoro-2-iodo-
  • SMILES FC1=CC(=C(C=C1)I)C(=O)O

Description

5-Fluoro-2-iodobenzoic acid features a strategically positioned iodine atom flanked by electron-withdrawing fluorine and carboxylic acid groups, enabling efficient cross-coupling transformations. This ortho-iodinated scaffold integrates readily into complex molecular architectures under standard palladium-catalyzed conditions.

Application

5-Fluoro-2-iodobenzoic acid serves as a versatile building block for palladium-catalyzed cross-coupling reactions, enabling efficient access to substituted biaryls and functionalized heterocycles. The ortho-iodo group exhibits high reactivity in Suzuki, Stille, and Negishi couplings, while the meta-fluoro and carboxylic acid functionalities provide orthogonal handles for further derivatization. Its bench-stable crystalline form facilitates handling and purification, making it well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • PFIZER INC.; BAILEY, Simon; BURKE, Benjamin, Joseph; COLLINS, Michael, Raymond; CUI, Jingrong, Jean; DEAL, Judith, Gail; HOFFMAN, Robert, Louis; HUANG, Qinhua; JOHNSON, Ted, William; KANIA, Robert, Steven; KATH, John, Charles; LE, Phuong, Thi, Quy; MCTIGUE, Michele, Ann; PALMER, Cynthia, Louise; RICHARDSON, Paul, Francis; SACH, Neal, William Patent: WO2013/132376 A1, 2013 ; Location in patent: Page/Page column 151 ;
  • Route2
    • null|null
      52548-59-1
    • 2-Amino-5-fluorobenzoic acid hydrochloride|CS-0666759
      52548-62-6
    • In-stock
      Maleic acid|CS-0015079
      110-16-7
    • ~%
    • In-stock
      5-Fluoro-2-iodobenzoic acid|CS-W008430
      52548-63-7

    References

    • Hoffmann-La Roche Inc. Patent: US4006144 A1, 1977 ;
  • Route3

    References

    • Rajsner; Metysova; Svatek; et al. Collection of Czechoslovak Chemical Communications, 1975 , vol. 40, # 3 p. 719 - 737

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   37.3
  • LogP   2.1285
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   1

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