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CS-W001157 4
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6-Iodo-2,3-dihydrobenzo[b][1,4]dioxine

  • CAS No. 57744-67-9

  • Cat. No. CS-0063836
  • Purity≥97%
  • MDL No.MFCD00221460

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

6-Iodo-2,3-dihydrobenzo[b][1,4]dioxine|CS-0063836

Structure of 57744-67-9

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General Information

  • CAS No. 57744-67-9
  • Cat. No. CS-0063836
  • Purity ≥97%
  • MDL No. MFCD00221460
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇IO₂
  • Molecular Weight 262.04
  • Synonym(s) 6-Iodo-2,3-dihydro-1,4-benzodioxine
  • SMILES IC1=CC=C(OCCO2)C2=C1

Description

6-Iodo-2,3-dihydrobenzo[b][1,4]dioxine offers a reactive iodine handle positioned within a stable, electron-rich heterocyclic framework. This moiety enables efficient coupling in palladium-catalyzed cross-coupling reactions, facilitating the construction of complex biaryl architectures. The molecule's bench-stable nature and compatibility with standard reaction conditions streamline integration into synthetic workflows.

Application

6-Iodo-2,3-dihydrobenzo[b][1,4]dioxine serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its stable iodide functionality. The dihydrobenzodioxine core provides rigidity and metabolic stability, while the iodine substituent facilitates efficient C–C bond formation under standard conditions. Its bench-stable nature and compatibility with diverse functional groups make it ideal for constructing complex heterocyclic scaffolds in API development.

Synthesis

  • Route1

    References

    • SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; CHIOSIS, Gabriela; TALDONE, Tony; SUN, Weilin Patent: WO2011/44394 A1, 2011 ; Location in patent: Page/Page column 110 ;
  • Route2

    References

    • Sosnowski, Maciej; Skulski, Lech Molecules, 2005 , vol. 10, # 2 p. 401 - 406
  • Route3

    References

    • Tetrahedron Letters, , vol. 37, # 14 p. 2441 - 2444

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05
Signal Word : Danger
UN#: 1760
Class : 8
Packing Group : Ⅱ
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P280-P302+P352

Quality Control

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Computational Chemistry Data

  • TPSA   18.46
  • LogP   2.0624
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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