N-Bromosaccharin (NBSac)

Introduction

N-Bromosaccharin (NBSac) is a strong oxidizing and chlorinating agent. It is a white powder, easy to handle, with its melting point at 160-170 °C. It is soluble in organic solvents, for example in alcohols, acetonitrile, tetrachloromethane, ethyl acetate, trichloromethane, acetone, and 1,4-dioxane. N-Bromosaccharin has been proven to be a useful and alternative reagent for diverse organic transformations, such as halogenation of aromatic compounds, co-halogenation of alkenes, oxidation of alcohols, halogenation of benzylic and carbonylic positions, etc. N-Bromosaccharin [1] can easily be prepared by bromination of the sodium salt of saccharin which is commonly available, non-corrosive, and non-toxic.

Figure 1

References

• 1 de Souza SPL. da Silva JFM. de Mattos MCS. Synth. Commun.  2003,  33:  935 
• 2 Iranpoor N. Firouzabadi H. Azadi R. Ebrahimzadeh F. Can. J. Chem.  2006,  84:  69 
• 3 Firouzabadi H. Iranpoor N. Ebrahimzadeh F. Tetrahedron Lett.  2006,  47:  1771 
• 4 Urankar D. Rutar I. Modec B. Dolenc D. Eur. J. Org. Chem.  2005,  2349 
• 5 Khazaei A. Rostami A. Aminimanesh A. J. Chin. Chem. Soc.  2006,  53:  437 
• 6 de Souza SPL. da Silva JFM. de Mattos MCS. Heterocycl. Commun.  2003,  9:  31 
• 7 Khazaei A. Aminimanesh A. Rostami A. Phosphorus Sulfur Relat. Elem.  2004,  179:  2483 
• 8 de Souza SPL. da Silva JFM. de Mattos MCS.
  J. Braz. Chem. Soc.  2003,  14:  832