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CS-W001157 4
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2-(2-Bromoethyl)oxirane

  • CAS No. 13287-42-8

  • Cat. No. CS-0158422
  • Purity≥97%
  • MDL No.MFCD11040246

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

2-(2-Bromoethyl)oxirane|CS-0158422

Structure of 13287-42-8

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General Information

  • CAS No. 13287-42-8
  • Cat. No. CS-0158422
  • Purity ≥97%
  • MDL No. MFCD11040246
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₄H₇BrO
  • Molecular Weight 151.00
  • Synonym(s) 4-Bromo-1,2-epoxy-butane
  • SMILES C(CBr)C1CO1

Description

2-(2-Bromoethyl)oxirane is a highly reactive epoxide featuring a bromoethyl side chain, enabling site-specific conjugation in synthetic and bioconjugation workflows. This bifunctional architecture combines ring strain-driven reactivity with a latent electrophilic handle, facilitating efficient coupling under mild conditions. The molecule demonstrates excellent stability during storage and compatibility with diverse functional groups.

Application

2-(2-Bromoethyl)oxirane serves as a versatile bifunctional building block in synthetic organic chemistry, enabling efficient ring-opening reactions and subsequent functionalization. The epoxide moiety reacts selectively with nucleophiles under mild conditions, while the pendant bromide supports further coupling via SN2 or transition-metal-catalyzed processes. Its bench-stable nature and compatibility with diverse functional groups make it ideal for constructing complex scaffolds in medicinal chemistry and materials science.

Synthesis

  • Route1
    • null|null
      5162-44-7
    • ~91%
    • In-stock
      2-(2-Bromoethyl)oxirane|CS-0158422
      13287-42-8

    References

    • Dennis, Mark; Hall, Louise M.; Murphy, Patrick J.; Thornhill, Andrew J.; Nash, Robert; Winters, Ana L.; Hursthouse, Michael B.; Light, Mark E.; Horton, Peter Tetrahedron Letters, 2003 , vol. 44, # 15 p. 3075 - 3080
  • Route2
    • null|null
      847934-57-0
    • ~%
    • In-stock
      2-(2-Bromoethyl)oxirane|CS-0158422
      13287-42-8

    References

    • Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, , vol. 150, p. 1058 Annales de Chimie (Cachan, France), , vol. <8> 24, p. 376
  • Route3

    References

    • Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, , vol. 149, p. 297

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS02,GHS05,GHS07,GHS08
Signal Word : Danger
UN#: 1993
Class : 3
Packing Group : Ⅲ
Hazard Statements : H226-H302-H315-H318-H335-H373
Precautionary Statements : P210-P233-P240-P241-P242-P243-P260-P264-P270-P271-P280-P301+P310-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P310-P312-P314-P330-P332+P313-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   12.53
  • LogP   1.1702
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   2

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