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(2-Iodo-ethyl)-carbamic acid benzyl ester

  • CAS No. 68373-12-6

  • Cat. No. CS-0208775
  • Purity≥97%
  • MDL No.MFCD09951822

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

(2-Iodo-ethyl)-carbamic acid benzyl ester|CS-0208775

Structure of 68373-12-6

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General Information

  • CAS No. 68373-12-6
  • Cat. No. CS-0208775
  • Purity ≥97%
  • MDL No. MFCD09951822
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₂INO₂
  • Molecular Weight 305.11
  • Synonym(s) BENZYL 2-IODOETHYLCARBAMATE
  • SMILES ICCNC(OCC1=CC=CC=C1)=O

Description

This boronate ester features a reactive iodoethyl group paired with a carbamic acid benzyl ester moiety, enabling efficient coupling in C–N bond formation. The pendant benzyl carbamate offers controlled release and enhanced solubility, while the iodide facilitates palladium-catalyzed transformations under standard conditions.

Application

(2-Iodoethyl)carbamic acid benzyl ester serves as a versatile alkylating agent in synthetic organic chemistry, enabling efficient introduction of the (2-iodoethyl)carbamate moiety. Its stability under standard bench conditions and compatibility with nucleophilic substitution reactions facilitate straightforward incorporation into peptide derivatives, heterocyclic scaffolds, and bioconjugation workflows. The benzyl ester group provides convenient orthogonal protection and facilitates purification via chromatography or crystallization.

Synthesis

  • Route1

    References

    • Van Staveren, Dave R.; Mundwiler, Stefan; Hoffmanns, Ulrich; Pak, Jae Kyoung; Spingler, Bernhard; Metzler-Nolte, Nils; Alberto, Roger Organic and Biomolecular Chemistry, 2004 , vol. 2, # 18 p. 2593 - 2603
  • Route2
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      501-53-1
    • ~%
    • In-stock
      (2-Iodo-ethyl)-carbamic acid benzyl ester|CS-0208775
      68373-12-6

    References

    • Lindley Australian Journal of Chemistry, 1959 , vol. 12, p. 296
  • Route3
    • 2-Iodoethan-1-amine|CS-0286771
      52689-15-3
    • null|null
      501-53-1
    • ~%
    • In-stock
      (2-Iodo-ethyl)-carbamic acid benzyl ester|CS-0208775
      68373-12-6

    References

    • Katchalski; Ben-Ishai Journal of Organic Chemistry, 1950 , vol. 15, p. 1067,1071

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-H332-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   38.33
  • LogP   2.3478
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   4

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