Synlett 2008(10): 1579-1580  
DOI: 10.1055/s-2008-1072785
© Georg Thieme Verlag Stuttgart · New York

1,2-Dibromoethane - A Versatile Reagent in Organic Synthesis

Bhaskar Reddy Aluri*
Institut für Biochemie/Anorganische Chemie, Ernst-Moritz-Arndt-Universität Greifswald, Felix-Hausdorff Str. 4, 17487 Greifswald, Germany
e-Mail: [email protected];
Further Information

Publication History

Publication Date:
07 May 2008 (online)


1,2-Dibromoethane (ethylene dibromide) is commonly used as an ‘entrainment reagent’ to chemically activate magnesium in Grignard reagents. It reacts with magnesium to expose a clean, reactive surface capable of converting otherwise unreactive halides into Grignard reagents. [1] It has many advantages over other entrainment agents. It reacts with magnesium to give MgBr2 and ethylene as byproducts and hence does not introduce a second Grignard reagent to the system. 1,2-Dibromoethane is also a useful reagent for activating zinc. [2] [3] This reagent can be used as a source of electrophilic bromine for bromination of carbanions, [4] and also acts as an alkylating agent with many enolates. [5] 1,2-Dibromoethane is a precursor to numerous 1,2-disubstituted ethane derivatives, for example 1,2-ethanedithiol. [6] In addition, it acts as a sacrificial reductant in the conversion of thiocarbonyl compounds to carbonyl compounds, [7] and as an excellent oxidizer in domino carbopalladation-cyclization processes. [8] It was used as a scavenger of lead antiknock agents in gasoline and as a soil fumigant for fumigation of grains and fruits until the early 1980s. It is a useful intermediate in the synthesis of dyes and pharmaceuticals.


  • 1 Pearson DE. Cowan D. Beckler JD. J. Org Chem.  1959,  24:  504 
  • 2 Carsten S. Daniel R. Wolfgang W. Chem. Eur. J.  2006,  12:  9186 
  • 3 Aerssens MHPJ. van der Heiden R. Heus M. Brandsma L. Synth. Commun.  1990,  20:  3421 
  • 4a Greene AE. Muller J.-C. Ourisson G. Tetrahedron Lett.  1972,  24:  2489 
  • 4b Greene AE. Muller J.-C. Ourisson G. J. Org. Chem.  1974,  39:  186 
  • 5 Newman MS. DeVries V. Darlak R. J. Org. Chem.  1966,  31:  2171 
  • 6 Kooyman JGA. Hendriks HPG. Montijn PP. Brandsma L. Arens JF. Recl. Trav. Chim. Pays-Bas  1968,  87:  69 
  • 7a Ley SV. Meerholz CA. Barton DHR. Tetrahedron  1981,  37:  213 
  • 7b Ley SV. Meerholz CA. Barton DHR. Tetrahedron Lett.  1980,  21:  1785 
  • 8 Dong CG. Yeung P. Hu QS. Org. Lett.  2007,  9:  363 
  • 9 Lesot P. Merlet D. Sarfati M. Courtieu J. Zimmermann H. Luz Z. J. Am. Chem. Soc.  2002,  124:  10071 
  • 10 Fieser LF. Fieser M. Reagents for Organic Synthesis   Vol. 1:  Wiley-VCH; New York: 1967.  p.657 
  • 11 Ito S. Hashino S. Morita N. Yoshifuji M. Hirose D. Takahashi M. Kawazoe Y. Tetrahedron  2007,  63:  10246 
  • 12 Ortega-Alfaro MC. Alcantara O. Orrala M. López-Cortés JG. Toscano RA. Alvarez-Toledano C. Organometallics  2007,  26:  1895 
  • 13 Cappello V. Baumgartner J. Dransfeld A. Hassler K. Eur. J. Inorg. Chem.  2006,  4589