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

  • CAS No. 52415-00-6

  • Cat. No. CS-0098648
  • Purity≥97%
  • MDL No.None

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

4-Iodo-2-methyl-1-nitrobenzene|CS-0098648

Structure of 52415-00-6

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General Information

  • CAS No. 52415-00-6
  • Cat. No. CS-0098648
  • Purity ≥97%
  • MDL No. None
  • 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-2-nitrotoluene
  • SMILES O=[N+]([O-])C1=CC=C(C=C1C)I

Description

4-Iodo-2-methyl-1-nitrobenzene features a nitro group at the para position relative to iodine, creating a strongly electron-deficient aromatic system ideal for palladium-catalyzed cross-coupling reactions. The methyl substituent enhances regioselectivity in subsequent functionalization steps. This bench-stable compound integrates readily into complex molecular architectures under standard conditions.

Application

4-Iodo-2-methyl-1-nitrobenzene serves as a versatile building block in cross-coupling chemistry, enabling efficient Suzuki and Stille reactions due to the ortho-methyl group’s steric and electronic influence. The iodide functionality provides high reactivity under mild conditions, while the nitro group offers stability and compatibility with standard synthetic workflows. Its bench-stable nature and predictable regioselectivity facilitate reliable construction of substituted aromatic scaffolds for medicinal chemistry and materials applications.

Synthesis

  • Route1

    References

    • Bao, Chunyan; Jin, Ming; Li, Bo; Xu, Yaodong; Jin, Jingyan; Zhu, Linyong Organic and Biomolecular Chemistry, 2012 , vol. 10, # 27 p. 5238 - 5244
  • Route2
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      108-44-1
    • ~%
    • In-stock
      4-Iodo-2-methyl-1-nitrobenzene|CS-0098648
      52415-00-6

    References

    • Bao, Chunyan; Jin, Ming; Li, Bo; Xu, Yaodong; Jin, Jingyan; Zhu, Linyong Organic and Biomolecular Chemistry, 2012 , vol. 10, # 27 p. 5238 - 5244
  • Route3
    • null|null
      636-98-6
    • ~%
    • In-stock
      4-Iodo-2-methyl-1-nitrobenzene|CS-0098648
      52415-00-6

    References

    • Bartoli, G.; Bosco, M.; Dalpozzo, R. Tetrahedron Letters, 1985 , vol. 26, # 1 p. 115 - 118

Safety Information

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GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H311-H331
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P361-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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