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CS-W001157 4
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Methyl 3-iodo-4-methylbenzoate

  • CAS No. 90347-66-3

  • Cat. No. CS-0007663
  • Purity≥98%
  • MDL No.MFCD00230583

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

Methyl 3-iodo-4-methylbenzoate|CS-0007663

Structure of 90347-66-3

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General Information

  • CAS No. 90347-66-3
  • Cat. No. CS-0007663
  • Purity ≥98%
  • MDL No. MFCD00230583
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₉IO₂
  • Molecular Weight 276.07
  • Synonym(s) Methyl 3-iodo-p-toluate
  • SMILES O=C(OC)C1=CC=C(C)C(I)=C1

Description

Methyl 3-iodo-4-methylbenzoate features a para-methyl group and a meta-iodo substituent on the aromatic ring, delivering enhanced electrophilic reactivity for palladium-catalyzed cross-coupling reactions. The ester functionality provides solubility in common organic solvents and stability under standard bench conditions, enabling efficient incorporation into complex molecular architectures.

Application

Methyl 3-iodo-4-methylbenzoate serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling efficient construction of biaryl and heteroaryl architectures. The iodide group facilitates reliable Suzuki, Stille, and Negishi couplings under standard conditions, while the methyl and ester functionalities provide orthogonal handles for further functionalization. Bench-stable and readily purified by column chromatography, it is well-suited for iterative synthesis workflows in medicinal chemistry and process development.

Synthesis

  • Route1
    • null|null
      67-56-1
    • In-stock
      3-Iodo-4-methylbenzoic acid|CS-W020661
      82998-57-0
    • ~97%
    • In-stock
      Methyl 3-iodo-4-methylbenzoate|CS-0007663
      90347-66-3

    References

    • 3-V BIOSCIENCES, INC.; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W. Patent: WO2014/8197 A1, 2014 ; Location in patent: Page/Page column 71 ;
  • Route2
    • Methyl 3-amino-4-methylbenzoate Nilotinib Impurity|CS-0229205
      18595-18-1
    • ~%
    • In-stock
      Methyl 3-iodo-4-methylbenzoate|CS-0007663
      90347-66-3

    References

    • US2008/182837 A1, ; Page/Page column 30 ;
  • Route3

    References

    • US2010/197659 A1, ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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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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