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((2-Iodoethoxy)methyl)benzene

  • CAS No. 54555-84-9

  • Cat. No. CS-0146879
  • Purity≥98%
  • MDL No.MFCD10574996

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

((2-Iodoethoxy)methyl)benzene|CS-0146879

Structure of 54555-84-9

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General Information

  • CAS No. 54555-84-9
  • Cat. No. CS-0146879
  • Purity ≥98%
  • MDL No. MFCD10574996
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₁IO
  • Molecular Weight 262.09
  • Synonym(s) None
  • SMILES ICCOCC=1C=CC=CC1

Description

This iodomethyl ether features a benzyl-protected ether linkage enabling selective C–O bond formation. The iodo group facilitates efficient palladium-catalyzed coupling reactions under mild conditions, offering reliable functionalization in synthetic sequences. The bench-stable, moisture-tolerant structure simplifies handling during complex molecule assembly.

Application

((2-Iodoethoxy)methyl)benzene serves as a versatile bifunctional building block for C–C and C–heteroatom bond formation. The iodide moiety enables reliable Suzuki, Stille, and Negishi coupling reactions, while the benzyloxyether functionality offers orthogonal reactivity for selective transformations. Its bench-stable nature and compatibility with standard synthetic protocols make it ideal for constructing complex molecular architectures in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • King, Bryan W. Patent: US2004/266751 A1, 2004 ; Location in patent: Page/Page column 20 ;
  • Route2
    • Benzyl-PEG1-MS|CS-0147939
      58841-52-4
    • ~90%
    • In-stock
      ((2-Iodoethoxy)methyl)benzene|CS-0146879
      54555-84-9

    References

    • Mahboobi, Siavosh; Bernauer, Karl Helvetica Chimica Acta, 1988 , vol. 71, p. 2034 - 2041
  • Route3

    References

    • Zhao, Yingsheng; Chen, Gong Organic Letters, 2011 , vol. 13, # 18 p. 4850 - 4853

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2810
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301+H311+H331
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P361+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   9.23
  • LogP   2.6382
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   4

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