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CS-W001157 4
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2-Iodo-6-methylbenzoic acid

  • CAS No. 54811-50-6

  • Cat. No. CS-0131360
  • Purity≥97%
  • MDL No.MFCD01310823

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

2-Iodo-6-methylbenzoic acid|CS-0131360

Structure of 54811-50-6

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General Information

  • CAS No. 54811-50-6
  • Cat. No. CS-0131360
  • Purity ≥97%
  • MDL No. MFCD01310823
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇IO₂
  • Molecular Weight 262.04
  • Synonym(s) 6-Iodo-o-toluic acid, 2-Carboxy-3-iodotoluene
  • SMILES O=C(O)C1=C(C)C=CC=C1I

Description

2-Iodo-6-methylbenzoic acid features a sterically hindered aromatic core with complementary iodine and methyl substituents positioned ortho to the carboxylic acid group. This arrangement enables efficient cross-coupling reactions while maintaining stability under standard conditions. The electron-deficient aryl iodide integrates readily into complex molecular architectures, offering a reliable handle for C–C bond formation in synthetic workflows.

Application

2-Iodo-6-methylbenzoic acid serves as a versatile building block for palladium-catalyzed cross-coupling reactions, enabling efficient C–C bond formation in the synthesis of substituted biaryls and functionalized aromatic systems. The iodo group exhibits high reactivity under standard Suzuki, Stille, and Negishi conditions, while the carboxylic acid and methyl groups provide orthogonal handles for further derivatization. Bench-stable and readily purified by recrystallization, it functions reliably in multi-step synthetic sequences targeting complex pharmaceutical intermediates and agrochemical scaffolds.

Synthesis

  • Route1
    • o-Toluic acid Tolvaptan  Impurity|CS-0229343
      118-90-1
    • ~98%
    • In-stock
      2-Iodo-6-methylbenzoic acid|CS-0131360
      54811-50-6

    References

    • Pospisil, Jiri; Mueller, Christoph; Fuerstner, Alois Chemistry - A European Journal, 2009 , vol. 15, # 24 p. 5956 - 5968
  • Route2

    References

    • INTELLIKINE, INC. Patent: WO2009/88986 A1, 2009 ; Location in patent: Page/Page column 78-79 ; WO 2009/088986 A1
  • Route3
    • null|null
      17264-71-0
    • ~85%
    • In-stock
      2-Iodo-6-methylbenzoic acid|CS-0131360
      54811-50-6

    References

    • Mei, Tian-Sheng; Giri, Ramesh; Maugel, Nathan; Yu, Jin-Quan Angewandte Chemie - International Edition, 2008 , vol. 47, # 28 p. 5215 - 5219

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   37.3
  • LogP   2.29782
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   1

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