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5-Fluoro-2-iodobenzaldehyde

  • CAS No. 877264-44-3

  • Cat. No. CS-0038109
  • Purity≥98%
  • MDL No.None

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

5-Fluoro-2-iodobenzaldehyde|CS-0038109

Structure of 877264-44-3

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General Information

  • CAS No. 877264-44-3
  • Cat. No. CS-0038109
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄FIO
  • Molecular Weight 250.01
  • Synonym(s) benzaldehyde, 5-fluoro-2-iodo-
  • SMILES C1=C(C=C(C=O)C(=C1)I)F

Description

5-Fluoro-2-iodobenzaldehyde is a halogenated aromatic aldehyde featuring fluorine and iodine substituents at meta and ortho positions relative to the aldehyde group. This electron-deficient scaffold enables direct functionalization in cross-coupling reactions, offering enhanced reactivity and selectivity in transition metal-catalyzed transformations. The molecule exhibits bench-stable handling characteristics and compatibility with diverse reaction conditions.

Application

5-Fluoro-2-iodobenzaldehyde serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling efficient construction of biaryl and heteroaryl scaffolds. The ortho-iodo group facilitates palladium-catalyzed coupling with boronic acids, esters, and amines, while the aldehyde functionality permits further derivatization via reductive amination or nucleophilic addition. Its bench-stable nature and compatibility with diverse functional groups make it well-suited for modular synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • PFIZER INC.; BAILEY, Simon; BURKE, Benjamin, Joseph; COLLINS, Michael, Raymond; CUI, Jingrong, Jean; DEAL, Judith, Gail; HOFFMAN, Robert, Louis; HUANG, Qinhua; JOHNSON, Ted, William; KANIA, Robert, Steven; KATH, John, Charles; LE, Phuong, Thi, Quy; MCTIGUE, Michele, Ann; PALMER, Cynthia, Louise; RICHARDSON, Paul, Francis; SACH, Neal, William Patent: WO2013/132376 A1, 2013 ; Location in patent: Page/Page column 152 ;
  • Route2

    References

    • Chemical Communications, , vol. 49, # 31 p. 3254 - 3256
  • Route3

    References

    • Chemical Communications, , vol. 49, # 31 p. 3254 - 3256

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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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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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