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3-Iodo-2-methylbenzoic acid

  • CAS No. 133232-56-1

  • Cat. No. CS-0015727
  • Purity≥95%
  • MDL No.MFCD00270112

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

3-Iodo-2-methylbenzoic acid|CS-0015727

Structure of 133232-56-1

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General Information

  • CAS No. 133232-56-1
  • Cat. No. CS-0015727
  • Purity ≥95%
  • MDL No. MFCD00270112
  • Storage RT, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇IO₂
  • Molecular Weight 262.04
  • Synonym(s) 3-iodo-2-methylbenzoate
  • SMILES O=C(O)C1=CC=CC(I)=C1C

Description

3-Iodo-2-methylbenzoic acid features a sterically hindered ortho-iodo substituent flanking a methyl group and carboxylic acid moiety, enabling direct functionalization in late-stage diversification. This bench-stable derivative integrates readily into cross-coupling protocols, delivering access to complex aromatic scaffolds with minimal purification overhead.

Application

3-Iodo-2-methylbenzoic acid serves as a versatile building block for the synthesis of functionalized aromatic scaffolds, particularly in Suzuki-Miyaura and Stille coupling reactions. Its ortho-methyl group enhances regioselectivity in electrophilic substitutions, while the carboxylic acid facilitates derivatization via amide or ester formation. The iodine substituent provides high reactivity in cross-coupling protocols, enabling efficient access to biaryl architectures. Bench-stable and readily purified by recrystallization, it functions as a reliable intermediate in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Kung, Pei-Pei; Funk, Lee; Meng, Jerry; Collins, Michael; Zhou, Joe Zhongxiang; Catherine Johnson; Ekker, Anne; Wang, Jeff; Mehta, Pramod; Yin, Min-Jean; Rodgers, Caroline; Davies II, Jay F.; Bayman, Eileen; Smeal, Tod; Maegley, Karen A.; Gehring, Michael R. Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 23 p. 6273 - 6278
  • Route2
    • o-Toluic acid Tolvaptan  Impurity|CS-0229343
      118-90-1
    • ~1%
    • In-stock
      3-Iodo-2-methylbenzoic acid|CS-0015727
      133232-56-1
    • In-stock
      5-Iodo-2-methylbenzoic acid|CS-D1105
      54811-38-0

    References

    • EP1642881 A1, ; Page/Page column 6 ;
  • Route3

    References

    • EP1595862 A1, ; Page/Page column 11-12 ;

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

Quality Control

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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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