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

  • CAS No. 755027-21-5

  • Cat. No. CS-0059279
  • Molecule weight268.48
  • Purity≥96%
  • MDL No.MFCD09753735

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

4-Chloro-1-iodo-2-methoxybenzene|CS-0059279

Structure of 755027-21-5

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General Information

  • CAS No. 755027-21-5
  • Cat. No. CS-0059279
  • Purity ≥96%
  • MDL No. MFCD09753735
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆ClIO
  • Molecular Weight 268.48
  • Synonym(s) 5-Chloro-2-iodoanisole
  • SMILES COC1=CC(Cl)=CC=C1I

Description

4-Chloro-1-iodo-2-methoxybenzene features a strategically positioned iodine atom enabling efficient palladium-catalyzed cross-coupling reactions. The ortho-methoxy group enhances solubility and stabilizes reaction intermediates, while the chloro substituent offers orthogonal reactivity. This dual-functional aryl halide integrates readily into complex molecular architectures under standard conditions.

Application

4-Chloro-1-iodo-2-methoxybenzene serves as a versatile diaryl building block in cross-coupling chemistry, enabling palladium-catalyzed reactions such as Suzuki-Miyaura and Stille couplings. The ortho-iodo and para-chloro groups provide complementary reactivity for sequential functionalization, while the methoxy group enhances solubility and modulates electronic properties. Bench-stable and amenable to standard purification methods, it facilitates efficient synthesis of complex aryl scaffolds relevant to pharmaceutical and agrochemical development.

Synthesis

  • Route1

    References

    • Jakab, Gergely; Hosseini, Abolfazl; Hausmann, Heike; Schreiner, Peter R. Synthesis (Germany), 2013 , vol. 45, # 12 art. no. SS-2013-C0157-ST, p. 1635 - 1640
  • Route2

    References

    • Hanford; Adams Journal of the American Chemical Society, 1935 , vol. 57, p. 1592,1594
  • Route3

    References

    • Hubig, S. M.; Jung, W.; Kochi, J. K. Journal of Organic Chemistry, 1994 , vol. 59, # 21 p. 6233 - 6244

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

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Computational Chemistry Data

  • TPSA   9.23
  • LogP   2.9532
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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