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CS-W001157 4
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1-Iodo-2-methyl-3-nitrobenzene

  • CAS No. 41252-98-6

  • Cat. No. CS-0041327
  • Purity≥98%
  • MDL No.MFCD08272202

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

1-Iodo-2-methyl-3-nitrobenzene|CS-0041327

Structure of 41252-98-6

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General Information

  • CAS No. 41252-98-6
  • Cat. No. CS-0041327
  • Purity ≥98%
  • MDL No. MFCD08272202
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆INO₂
  • Molecular Weight 263.03
  • Synonym(s) 5-IODO-6-METHYL-1-NITROBENZENE
  • SMILES CC1=C(I)C=CC=C1[N+]([O-])=O

Description

1-Iodo-2-methyl-3-nitrobenzene features a strategically positioned iodine atom flanked by a methyl group and a nitro substituent, enabling selective cross-coupling reactions. The electron-deficient aromatic ring enhances reactivity in palladium-catalyzed transformations, while the bench-stable, moisture-tolerant structure simplifies handling in synthetic workflows.

Application

1-Iodo-2-methyl-3-nitrobenzene 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 palladium-catalyzed coupling under standard conditions, while the ortho-methyl and meta-nitro substituents provide steric and electronic control, enhancing regioselectivity. This compound exhibits good bench stability and is amenable to purification via flash chromatography, making it well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Somei, Masanori; Amari, Hirokuni; Makita, Yoshihiko Chemical & Pharmaceutical Bulletin, 1986 , vol. 34, # 9 p. 3971 - 3973
  • Route2
    • null|null
      88-72-2
    • ~77%
    • In-stock
      4-Iodo-2-nitrotoluene|CS-W002239
      41252-97-5
    • In-stock
      1-Iodo-2-methyl-3-nitrobenzene|CS-0041327
      41252-98-6

    References

    • Chaikovskii; Filimonov; Funk Russian Journal of Organic Chemistry, 2009 , vol. 45, # 9 p. 1349 - 1352
  • Route3
    • null|null
      88-72-2
    • ~65%
    • In-stock
      4-Iodo-2-nitrotoluene|CS-W002239
      41252-97-5
    • null|null
      10388-22-4
    • In-stock
      1-Iodo-2-methyl-3-nitrobenzene|CS-0041327
      41252-98-6

    References

    • Chaikovskii; Filimonov; Funk Russian Journal of Organic Chemistry, 2009 , vol. 45, # 9 p. 1349 - 1352

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

Quality Control

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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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