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1-Boc-3-iodoazetidine

  • CAS No. 254454-54-1

  • Cat. No. CS-D0674
  • Purity≥98%
  • MDL No.MFCD09752821

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

1-Boc-3-iodoazetidine|CS-D0674

Structure of 254454-54-1

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General Information

  • CAS No. 254454-54-1
  • Cat. No. CS-D0674
  • Purity ≥98%
  • MDL No. MFCD09752821
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₄INO₂
  • Molecular Weight 283.11
  • Synonym(s) None
  • SMILES O=C(N1CC(C1)I)OC(C)(C)C

Description

1-Boc-3-iodoazetidine is a bench-stable, moisture-tolerant azetidine derivative featuring a Boc-protected nitrogen and a reactive iodide at the adjacent carbon. This combination enables direct functionalization in late-stage diversification, particularly in palladium-catalyzed cross-coupling reactions. The strained three-membered ring imparts high reactivity, while the Boc group ensures compatibility with standard synthetic workflows.

Application

1-Boc-3-iodoazetidine serves as a versatile, bench-stable building block for the construction of bioactive azetidine-containing scaffolds. The Boc group provides orthogonal protection for nitrogen functionality, enabling selective deprotection and downstream functionalization. The iodine moiety facilitates efficient palladium-catalyzed cross-coupling reactions, including Suzuki, Stille, and Negishi couplings, allowing rapid diversification in medicinal chemistry and process development workflows. Its stability under standard handling conditions and compatibility with common synthetic protocols make it ideal for modular synthesis of complex heterocyclic systems.

Synthesis

  • Route1

    References

    • RAQUALIA PHARMA INC.; ANDO, Kazuo; IWATA, Yasuhiro Patent: WO2010/84767 A1, 2010 ; Location in patent: Page/Page column 47 ; WO 2010/084767 A1
  • Route2

    References

    • Claffey, Michelle M.; Helal, Christopher J.; Verhoest, Patrick R.; Kang, Zhijun; Fors, Kristina S.; Jung, Stanley; Zhong, Jiaying; Bundesmann, Mark W.; Hou, Xinjun; Lui, Shenping; Kleiman, Robin J.; Vanase-Frawley, Michelle; Schmidt, Anne W.; Menniti, Frank; Schmidt, Christopher J.; Hoffman, William E.; Hajos, Mihaly; McDowell, Laura; Oconnor, Rebecca E.; MacDougall-Murphy, Mary; Fonseca, Kari R.; Becker, Stacey L.; Nelson, Frederick R.; Liras, Spiros Journal of Medicinal Chemistry, 2012 , vol. 55, # 21 p. 9055 - 9068
  • Route3
    • tert-Butyl 3-(((trifluoromethyl)sulfonyl)oxy)azetidine-1-carboxylate|CS-1347034
      916899-83-7
    • ~%
    • In-stock
      1-Boc-3-iodoazetidine|CS-D0674
      254454-54-1

    References

    • WO2006/134487 A1, ; Page/Page column 41 ; WO 2006/134487 A1

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07,GHS09
Signal Word : Warning
UN#: 3082
Class : 9
Packing Group : Ⅲ
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   29.54
  • LogP   2.0407
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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