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CS-W001157 4
Total: USD 88.00

2-Iodo-1-methyl-4-nitrobenzene

  • CAS No. 7745-92-8

  • Cat. No. CS-W012471
  • Purity≥95%
  • MDL No.MFCD00024329

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

2-Iodo-1-methyl-4-nitrobenzene|CS-W012471

Structure of 7745-92-8

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General Information

  • CAS No. 7745-92-8
  • Cat. No. CS-W012471
  • Purity ≥95%
  • MDL No. MFCD00024329
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆INO₂
  • Molecular Weight 263.03
  • Synonym(s) 2-Iodo-4-nitrotoluene
  • SMILES O=[N+](C1=CC=C(C)C(I)=C1)[O-]

Description

2-Iodo-1-methyl-4-nitrobenzene features a sterically accessible iodine atom paired with a para-nitro group, enabling efficient cross-coupling reactions under mild conditions. The methyl substitution enhances solubility and stability in organic solvents, while the electron-deficient aryl ring facilitates palladium-catalyzed transformations. This compound serves as a key building block for functionalized arenes in medicinal chemistry and materials science.

Application

2-Iodo-1-methyl-4-nitrobenzene serves as a versatile building block in cross-coupling chemistry, enabling efficient Suzuki, Stille, and Negishi reactions due to its well-defined reactivity profile. The iodine moiety facilitates reliable coupling under mild conditions, while the methyl and nitro groups provide orthogonal functionalization sites. This compound exhibits excellent bench stability and is readily purified by recrystallization, making it ideal for iterative synthesis of complex aromatic scaffolds and functionalized heterocycles in medicinal and process chemistry workflows.

Synthesis

  • Route1
    • null|null
      99-99-0
    • ~88%
    • In-stock
      2-Iodo-1-methyl-4-nitrobenzene|CS-W012471
      7745-92-8

    References

    • Azarifar, Davood; Khosravi, Kaveh; Najminejad, Zohreh; Soleimani, Khadijeh Journal of the Iranian Chemical Society, 2012 , vol. 9, # 3 p. 321 - 326
  • Route2

    References

    • Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), , p. 1281 - 1286
  • Route3

    References

    • Chemische Berichte, , vol. 30, p. 3000 Chemische Berichte, , vol. 41, p. 2077

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07,GHS09
Signal Word : Warning
UN#: 3077
Class : 9
Packing Group : Ⅲ
Hazard Statements : H302-H312-H332-H401-H411
Precautionary Statements : P261-P264-P270-P271-P273-P280-P363-P391-P501

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Computational Chemistry Data

  • TPSA   43.14
  • LogP   2.50782
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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