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Methyl 3-iodo-2-methylbenzoate

  • CAS No. 52570-33-9

  • Cat. No. CS-0036226
  • Purity≥97%
  • MDL No.MFCD12923250

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

Methyl 3-iodo-2-methylbenzoate|CS-0036226

Structure of 52570-33-9

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General Information

  • CAS No. 52570-33-9
  • Cat. No. CS-0036226
  • Purity ≥97%
  • MDL No. MFCD12923250
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₉IO₂
  • Molecular Weight 276.07
  • Synonym(s) None
  • SMILES CC1=C(C=CC=C1C(=O)OC)I

Description

Methyl 3-iodo-2-methylbenzoate is a bench-stable, electron-deficient aromatic ester featuring a strategically positioned iodine atom at the meta position relative to the methyl ester group. This configuration enables direct coupling in palladium-catalyzed cross-coupling reactions without requiring additional protecting groups. The ortho-methyl substituent enhances regioselectivity and provides steric guidance during transformation.

Application

Methyl 3-iodo-2-methylbenzoate serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling efficient access to substituted biaryl and heteroaryl architectures. The iodide group facilitates reliable Suzuki, Stille, and Negishi couplings, while the methyl and ester functionalities provide orthogonal handles for further derivatization. Bench-stable and readily purified by flash chromatography, it supports scalable synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Bressy, Cyril; Alberico, Dino; Lautens, Mark Journal of the American Chemical Society, 2005 , vol. 127, # 38 p. 13148 - 13149
  • Route2
    • null|null
      67-56-1
    • In-stock
      3-Iodo-2-methylbenzoic acid|CS-0015727
      133232-56-1
    • ~89%
    • In-stock
      Methyl 3-iodo-2-methylbenzoate|CS-0036226
      52570-33-9

    References

    • PFIZER INC. Patent: WO2006/117669 A1, 2006 ; Location in patent: Page/Page column 41; 108 ;
  • Route3
    • null|null
      67-56-1
    • null|null
      52107-91-2
    • ~%
    • In-stock
      Methyl 3-iodo-2-methylbenzoate|CS-0036226
      52570-33-9

    References

    • TAKEDA PHARMACEUTICAL COMPANY LIMITED Patent: WO2008/16184 A1, 2008 ; Location in patent: Page/Page column 120-121 ;

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   26.3
  • LogP   2.38622
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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