Nitration of Aromatic Compounds Using N-bromosuccinimide, Sodium Nitrite and Wet SiO2 as a Mild and Selective System

Document Type : Research Article


Chemistry Department, College of Science, Shahid Chamran University of Ahvaz, P.O. Box 61357-43169 Ahvaz, I.R. IRAN


The nitration of aromatic compounds is one of the most important industrial processes and is the subject of a large body of literature. In this study, the use of N-bromosuccinimide in the presence of NaNO2 and wet SiO2 as a mild and safe method was studied for the nitration of aromatic compounds. These reactions occur under mild, neutral and heterogenic conditions. This system can be applied to a wide range of acid-sensitive substrates in comparison to traditional methods.


Main Subjects

[1] San Ju K., Parales R., Nitroaromatic Compounds, from Synthesis to Biodegradation, Microbiol.Mol. Biol .Rev., 74(2): 250-272 (2010).
[2] Niknam K., Zolfigol M.A., Madrakian E., Ghaemi E., Tribromoisocyanuric Acid/NaNO: A New Reagent for Mononitration of Phenols under Mild and Heterogeneous Conditions, S. Afr. J. Chem., 60: 109-112 (2007).
[3] Mellor J.M., Mittoo S., Parkes R., Millar R., Improved Nitrations Using Metal Nitrate–Sulfuric Acid Systems, Tetrahedron, 56(40): 8019-8024 (2000).
[5] Iranpoor N., Firouzabadi H., Nowrouzi N., Firouzabadi D., Highly Chemoselective Nitration of Aromatic Amines Using the Ph3P/Br2/AgNO3 System, Tetrahedron Lett., 47: 6879-6881 (2006).
[8] Zolfigol M.A., Khazaei A., Moosavi-Zare A., Zare A., Kruger H.G., Asgari Z., Khakyzadehad V., Rostami M.K., Design of Ionic Liquid 3-Methyl-1-Sulfonic Acid Imidazolium Nitrate as Reagent for the Nitration of Aromatic Compounds by in Situ Generation of NO2 in Acidic Media, J. Org. Chem., 77(7): 3640-3645 (2012).
[10] Wąsińska M., Korczewska A., Giurg M., Skarżewski J., Improved Protocol for Mononitration of Phenols with Bismuth(III) and Iron(III) NitratesSynth. Commun., 45: 143-150 (2015). 
[11] Nowrouzi N., Mehranpoor A.M., Bashiri E., Shayan Z., Aromatic Nitration Under Neutral Conditions Using N-Bromosuccinimide/Silver(I) Nitrate, Tetrahedron Lett., 53: 4841-4842 (2012).