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CS-W001157 4
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4-Chloro-2-iodo-1-methylbenzene

  • CAS No. 33184-48-4

  • Cat. No. CS-0134652
  • Purity≥98%
  • MDL No.MFCD00060661

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

4-Chloro-2-iodo-1-methylbenzene|CS-0134652

Structure of 33184-48-4

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General Information

  • CAS No. 33184-48-4
  • Cat. No. CS-0134652
  • Purity ≥98%
  • MDL No. MFCD00060661
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆ClI
  • Molecular Weight None
  • Synonym(s) 4-CHLORO-2-IODOTOLUENE
  • SMILES CC1=CC=C(Cl)C=C1I

Description

4-Chloro-2-iodo-1-methylbenzene features a strategically positioned iodine atom enabling efficient cross-coupling reactions, while the chloro and methyl groups provide orthogonal reactivity and steric modulation. This trifunctional aromatic scaffold integrates seamlessly into complex molecular architectures under standard conditions.

Application

4-Chloro-2-iodo-1-methylbenzene serves as a versatile biaryl building block in cross-coupling chemistry, enabling efficient Pd-catalyzed transformations such as Suzuki-Miyaura and Stille reactions. The ortho-iodo group exhibits high reactivity, while the meta-chloro and para-methyl substituents provide orthogonal functionalization potential and enhanced stability under standard reaction conditions. This compound facilitates the construction of complex substituted arenes with predictable regiochemistry and is well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • null|null
      95-79-4
    • ~68%
    • In-stock
      4-Chloro-2-iodo-1-methylbenzene|CS-0134652
      33184-48-4

    References

    • Lautens, Mark; Paquin, Jean-Francois; Piguel, Sandrine; Dahlmann, Marc Journal of Organic Chemistry, 2001 , vol. 66, # 24 p. 8127 - 8134
  • Route2
    • null|null
      106-43-4
    • ~%
    • In-stock
      4-Chloro-2-iodo-1-methylbenzene|CS-0134652
      33184-48-4
    • In-stock
      4-Chloro-3-iodotoluene|CS-0194930
      2401-22-1

    References

    • Journal of Organic Chemistry USSR (English Translation), , vol. 24, # 11 p. 2029 - 2035 Zhurnal Organicheskoi Khimii, , vol. 24, # 11 p. 2251 - 2258

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-H335
Precautionary Statements : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   0
  • LogP   3.25302
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   0

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