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CS-W001157 4
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Benzyl (2-bromoethyl)carbamate

  • CAS No. 53844-02-3

  • Cat. No. CS-W001870
  • Purity≥95%
  • MDL No.MFCD09909490

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

Benzyl (2-bromoethyl)carbamate|CS-W001870

Structure of 53844-02-3

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General Information

  • CAS No. 53844-02-3
  • Cat. No. CS-W001870
  • Purity ≥95%
  • MDL No. MFCD09909490
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₂BrNO₂
  • Molecular Weight 258.11
  • Synonym(s) N-Cbz-3-broMoethylaMine
  • SMILES BrCCNC(=O)OCc1ccccc1

Description

Benzyl (2-bromoethyl)carbamate delivers a reactive bromoethyl handle for nucleophilic substitution, enabling efficient conjugation in peptide synthesis and bioconjugation workflows. The benzyl carbamate moiety provides stability under standard conditions while the β-bromide facilitates rapid functionalization. This reagent combines synthetic versatility with reliable handling in air and moisture-sensitive applications.

Application

Benzyl (2-bromoethyl)carbamate serves as a versatile bifunctional building block in synthetic organic chemistry, enabling efficient introduction of both carbamate and bromoalkyl handles. It functions as a key intermediate in the synthesis of bioactive heterocycles and peptide mimetics, offering high stability under standard bench conditions. The bromoethyl moiety facilitates alkylation reactions with nucleophiles, while the benzyl carbamate group provides reliable protection for amines, supporting orthogonal functionalization strategies in complex molecule assembly.

Synthesis

  • Route1
    • In-stock
      2-Bromoethylammonium bromide|CS-W008659
      2576-47-8
    • null|null
      501-53-1
    • ~98%
    • In-stock
      Benzyl (2-bromoethyl)carbamate|CS-W001870
      53844-02-3

    References

    • Journal of Medicinal Chemistry, , vol. 24, # 4 p. 408 - 428
  • Route2
    • 2-(((Benzyloxy)carbonyl)amino)ethyl methanesulfonate|CS-0590456
      134307-72-5
    • ~99%
    • In-stock
      Benzyl (2-bromoethyl)carbamate|CS-W001870
      53844-02-3

    References

    • Advanced Synthesis and Catalysis, , vol. 354, # 8 p. 1519 - 1528
  • Route3
    • null|null
      107-09-5
    • null|null
      501-53-1
    • ~%
    • In-stock
      Benzyl (2-bromoethyl)carbamate|CS-W001870
      53844-02-3

    References

    • Journal of Organic Chemistry, , vol. 15, p. 1067,1071 Australian Journal of Chemistry, , vol. 12, p. 296

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-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   38.33
  • LogP   2.3077
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   4

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