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CS-W001157 4
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Benzyl 3-iodoazetidine-1-carboxylate

  • CAS No. 939759-26-9

  • Cat. No. CS-0045527
  • Purity≥95%
  • MDL No.MFCD09026510

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

Benzyl 3-iodoazetidine-1-carboxylate|CS-0045527

Structure of 939759-26-9

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General Information

  • CAS No. 939759-26-9
  • Cat. No. CS-0045527
  • Purity ≥95%
  • MDL No. MFCD09026510
  • Storage RT, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₂INO₂
  • Molecular Weight 317.12
  • Synonym(s) 1-Cbz-3-iodo-azetidine
  • SMILES IC1CN(C1)C(=O)OCC1=CC=CC=C1

Description

Benzyl 3-iodoazetidine-1-carboxylate is a sterically constrained, bench-stable heterocyclic building block featuring a reactive iodide at the 3-position of the azetidine ring. This electrophilic handle enables efficient late-stage functionalization via cross-coupling reactions, facilitating rapid access to diverse nitrogen-containing scaffolds in medicinal chemistry and chemical biology applications.

Application

Benzyl 3-iodoazetidine-1-carboxylate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to azetidine-containing scaffolds via palladium-catalyzed cross-coupling reactions. The iodide group facilitates reliable functionalization under standard coupling conditions, while the benzyl ester offers convenient deprotection and stability under routine reaction protocols. Its compact strained ring system enhances reactivity in cyclization and fragment coupling processes, making it valuable for medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • Yi, Jun; Lu, Xi; Sun, Yan-Yan; Xiao, Bin; Liu, Lei Angewandte Chemie - International Edition, 2013 , vol. 52, # 47 p. 12409 - 12413 Angew. Chem., 2013 , vol. 125, # 47 p. 12635 - 12639,5
  • Route2
    • null|null
      1379079-64-7
    • ~89%
    • In-stock
      Benzyl 3-iodoazetidine-1-carboxylate|CS-0045527
      939759-26-9

    References

    • Davis, Tyler A.; Danneman, Michael W.; Johnston, Jeffrey N. Chemical Communications, 2012 , vol. 48, # 45 p. 5578 - 5580
  • Route3
    • Benzyl 3-((methylsulfonyl)oxy)azetidine-1-carboxylate|CS-0484022
      1315368-95-6
    • ~%
    • In-stock
      Benzyl 3-iodoazetidine-1-carboxylate|CS-0045527
      939759-26-9

    References

    • Cheung, Chi Wai; Ren, Peng; Hu, Xile Organic Letters, 2014 , vol. 16, # 9 p. 2566 - 2569

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-P280-P302+P352

Quality Control

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Computational Chemistry Data

  • TPSA   29.54
  • LogP   2.4424
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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