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Methyl 2-iodo-3-nitrobenzoate

  • CAS No. 93415-79-3

  • Cat. No. CS-0105549
  • Purity≥97%
  • MDL No.MFCD00114906

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

Methyl 2-iodo-3-nitrobenzoate|CS-0105549

Structure of 93415-79-3

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General Information

  • CAS No. 93415-79-3
  • Cat. No. CS-0105549
  • Purity ≥97%
  • MDL No. MFCD00114906
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆INO₄
  • Molecular Weight 307.04
  • Synonym(s) SPECS AI-942/25034494
  • SMILES O=C(OC)C1=CC=CC([N+]([O-])=O)=C1I

Description

Methyl 2-iodo-3-nitrobenzoate features a strategically positioned iodine and nitro group on a methyl benzoate scaffold, enabling direct functionalization in cross-coupling reactions. The electron-deficient aromatic ring enhances reactivity in palladium-catalyzed transformations, while the ester moiety offers stability and solubility under standard conditions.

Application

Methyl 2-iodo-3-nitrobenzoate serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling efficient C–C bond formation at the iodine site. The ortho-nitro group enhances reactivity and directs regioselective functionalization, while the ester moiety provides stability and ease of purification. This compound facilitates access to substituted aromatic scaffolds relevant in medicinal chemistry and materials science.

Synthesis

  • Route1
    • null|null
      67-56-1
    • In-stock
      2-Iodo-3-nitrobenzoic acid|CS-B1198
      5398-69-6
    • ~93%
    • In-stock
      Methyl 2-iodo-3-nitrobenzoate|CS-0105549
      93415-79-3

    References

    • Takeda Pharmaceutical Company Limited Patent: EP2141150 A1, 2010 ; Location in patent: Page/Page column 103-104 ;
  • Route2

    References

    • US6495541 B1, ;
  • Route3

    References

    • Tetrahedron, , vol. 62, # 20 p. 4829 - 4837

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
Precautionary Statements : P264-P270-P330

Quality Control

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Computational Chemistry Data

  • TPSA   69.44
  • LogP   1.986
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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