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CS-W001157 4
Total: USD 88.00

4-Fluoro-3-iodobenzaldehyde

  • CAS No. 227609-88-3

  • Cat. No. CS-0312191
  • Molecule weight250.01
  • Purity≥98%
  • MDL No.None

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

4-Fluoro-3-iodobenzaldehyde|CS-0312191

Structure of 227609-88-3

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General Information

  • CAS No. 227609-88-3
  • Cat. No. CS-0312191
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄FIO
  • Molecular Weight 250.01
  • Synonym(s) 4-fluoro-3-iodobenzenecarbaldehyde
  • SMILES O=CC1=CC=C(C(I)=C1)F

Description

4-Fluoro-3-iodobenzaldehyde features a fluorinated aromatic ring bearing strategically positioned iodide and aldehyde functionalities. This combination enables direct incorporation into cross-coupling reactions, particularly Suzuki-Miyaura and Negishi transformations, where the iodide acts as a high-reactivity handle. The electron-withdrawing fluorine substituent modulates reactivity and enhances metabolic stability in bioactive molecule synthesis.

Application

4-Fluoro-3-iodobenzaldehyde serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling efficient access to substituted biaryl scaffolds. The ortho-iodo and para-fluoro groups offer orthogonal reactivity for sequential functionalization, while the aldehyde functionality permits facile derivatization via condensation or reduction. Bench-stable and compatible with standard reaction conditions, it facilitates streamlined synthesis of complex heterocycles and pharmaceutical intermediates.

Synthesis

  • Route1

    References

    • Xin, Zhili; Liu, Gang; Pei, Zhonghua; Szczepankiewicz, Bruce G.; Serby, Michael D.; Zhao, Hongyu Patent: US2004/214870 A1, 2004 ; Location in patent: Page 22 ; US 20040214870 A1
  • Route2
    • p-Fluorobenzenecarboxaldehyde Atorvastatin calcium|CS-0214005
      459-57-4
    • ~57%
    • In-stock
      4-Fluoro-3-iodobenzaldehyde|CS-0312191
      227609-88-3

    References

    • Kraszkiewicz, Lukasz; Sosnowski, Maciej; Skulski, Lech Synthesis, 2006 , # 7 p. 1195 - 1199
  • Route3
    • (4-Fluoro-3-iodophenyl)methanol|CS-0378751
      227609-87-2
    • ~%
    • In-stock
      4-Fluoro-3-iodobenzaldehyde|CS-0312191
      227609-88-3

    References

    • Carroll, William A.; Altenbach, Robert J.; Bai, Hao; Brioni, Jorge D.; Brune, Michael E.; Buckner, Steven A.; Cassidy, Christopher; Chen, Yiyuan; Coghlan, Michael J.; Daza, Anthony V.; Drizin, Irene; Fey, Thomas A.; Fitzgerald, Michael; Gopalakrishnan, Murali; Gregg, Robert J.; Henry, Rodger F.; Holladay, Mark W.; King, Linda L.; Kort, Michael E.; Kym, Philip R.; Milicic, Ivan; Tang, Rui; Turner, Sean C.; Whiteaker, Kristi L.; Yi, Lin; Zhang, Henry; Sullivan, James P. Journal of Medicinal Chemistry, 2004 , vol. 47, # 12 p. 3163 - 3179

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   17.07
  • LogP   2.2428
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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