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CS-W001157 4
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2-Hydroxy-4-iodobenzoic acid

  • CAS No. 16870-28-3

  • Cat. No. CS-0103689
  • Purity≥98%
  • MDL No.MFCD00061127

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

2-Hydroxy-4-iodobenzoic acid|CS-0103689

Structure of 16870-28-3

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General Information

  • CAS No. 16870-28-3
  • Cat. No. CS-0103689
  • Purity ≥98%
  • MDL No. MFCD00061127
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅IO₃
  • Molecular Weight 264.02
  • Synonym(s) 4-iodosalicylic acid
  • SMILES O=C(O)C1=CC=C(I)C=C1O

Description

2-Hydroxy-4-iodobenzoic acid features a hydroxyl group ortho to the carboxylic acid and an iodine substituent at the para position, enabling selective functionalization in cross-coupling reactions. The electron-withdrawing iodide enhances reactivity while the adjacent hydroxyl supports hydrogen bonding and solubility in polar solvents. This combination delivers robust performance in synthetic intermediates for pharmaceuticals and advanced materials.

Application

2-Hydroxy-4-iodobenzoic acid serves as a versatile building block for palladium-catalyzed cross-coupling reactions, enabling efficient access to biaryl and heteroaryl architectures. The ortho-hydroxyl group provides enhanced solubility and facilitates directed metalation, while the iodide acts as a reliable coupling handle under standard Suzuki, Stille, or Negishi conditions. Bench-stable and readily purified by recrystallization, it functions effectively in late-stage functionalization workflows and synthetic routes to pharmaceutical intermediates.

Synthesis

  • Route1
    • 4-Aminosalicylic acid Mesalazine  Impurity|CS-0229166
      65-49-6
    • ~85%
    • In-stock
      2-Hydroxy-4-iodobenzoic acid|CS-0103689
      16870-28-3

    References

    • PTC THERAPEUTICS, INC.; HWANG, Peter Seongwoo; TAKASUGI, James; REN, Hongyu; WILDE, Richard Gerald; TURPOFF, Anthony; AREFOLOV, Alexander; KARP, Gary Mitchell; CHEN, Guangming; CAMPBELL, Jeffrey Allen Patent: WO2006/19831 A1, 2006 ; Location in patent: Page/Page column 445 ;
  • Route2

    References

    • Galderma Research and Development S.N.C. Patent: US6689922 B1, 2004 ; Location in patent: Page column 30 ;
  • Route3

    References

    • Kuroda, Chiaki; Ochi, Atsushi; Nakane, Noritoshi; Umeyama, Takashi; Muto, Nobuko; Niimura, Nami; Teramoto, Yoshiki; Nogami, Hiroyuki; Reddy, Guvvala N. Bulletin of the Chemical Society of Japan, 2000 , vol. 73, # 2 p. 417 - 422

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H318-H412
Precautionary Statements : P264-P270-P273-P280-P330-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   57.53
  • LogP   1.695
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   1

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