Sodium Nitrite (NaNO₂): An Impressive and Efficient Nitrating/Nitrosating Reagent in Organic Synthesis

Abstract

This graphical review provides a concise overview of the key organic reactions reported in the literature that use sodium nitrite (NaNO₂) as a nitrating or nitrosating agent. It summarizes the diverse reactivity of this reagent with various substrates, leading to the functionalization and synthesis of a wide variety of useful organic molecules.

Key words

sodium nitrite - nitrating - nitrosating - functionalization - synthesis - catalytic reactions

Biosketches

Lamark Carlos I graduated in chemistry from the Federal University of Rio Grande do Norte in 2019. Currently, he is studying for an M.Sc. in pharmaceutical sciences at the same institute under the supervision of Prof. Dr. A. K. Jordão and Prof. Dr. E. G. Barbosa. His work involves the synthesis and antimalarial evaluation of new 1H-1,2,3-triazoles derived from melatonin and tryptamine.

Euzebio Guimarães Barbosa received his Ph.D. in chemistry from Campinas University (UNICAMP) in 2011 under the supervision of Prof. Dr. Marcia Miguel Castro Ferreira. Currently he is a professor at the Federal University of Rio Grande do Norte. His research interests focus on medicinal chemistry and computer-aided drug design.

Alessandro Kappel Jordão received his Ph.D. in chemistry from Fluminense Federal University (UFF) in 2010 under the supervision of Prof. Vitor Francisco Ferreira and Prof. Anna Claudia. Currently, he is a professor at the Federal University of Rio Grande do Norte. His research interests focus on the synthesis of heterocyclic compounds.

Sodium nitrite (NaNO₂) is a hygroscopic and crystalline inorganic salt that slowly oxidizes in air. It is highly soluble in water and slightly soluble in diethyl ether, methanol, and ethanol. Industrially, it is the most important salt produced from nitrous acid. It is obtained on large scale by the reaction between a mixture of nitrogen oxides and an alkaline solution of sodium hydroxide or sodium carbonate.[1a] [b] Sodium nitrite finds extensive use in the chemical and pharmaceutical industries for the production of nitroso and isonitroso compounds, and is utilized in diazotization reactions (especially for dyes) and the synthesis of pharmaceutical products (e.g., caffeine) and agricultural pesticides (e.g., pyramin). In the food industry, sodium nitrite is used as a preservative for cured meat products. It contributes to flavor enhancement, prevents discoloration, and protects against the growth and toxin production of Clostridium botulinum.[1h–k]

The applications of sodium nitrite in organic synthesis have been widely studied. NaNO₂, in mixtures with mineral or organic acids, results in the formation of unstable nitrous acid (HNO₂), a reactive species that readily participates in several reactions. Polyatomic species generated in situ, such as nitrosonium (NO⁺) and nitronium (NO₂ ⁺) ions, are capable of acting on several organic substrates.[1l] An important example is the reaction with primary aromatic amines to form aryl diazonium salts, which are widely used in modern organic synthesis. This reaction is exemplified by classic procedures such as those of Sandmeyer,[1`] [f] [g] Gomberg and Bachmann, and Balz and Schiemann, as well as the more robust methodologies developed by Heck and Matsuda.[1m,n]

The objective of this graphical review is to present methodologies that use sodium nitrite with different types of substrates for the synthesis of organic molecules, without involving the formation of aryl diazonium salt intermediates. NaNO₂, as a source of nitrite ions, has been used in various reactions as a nitrating and nitrosating agent. Examples include the direct nitration of arenes,[2] the nitrosation of secondary amines,[3] the synthesis of nitriles[6] and oximes,[7] the functionalization and formation of heterocycles,[8a] and catalytic reactions involving the cleavage and formation of C–C bonds.[9] [10] Additionally, sodium nitrite plays a role in oxidation and halogenation reactions, acting as a catalyst or co-catalyst for the synthesis of organic compounds, specifically carbonyl and halogenated aromatic compounds.[4,5,11]

This graphical review explores pioneering studies and contemporary synthetic methodologies that encompass a variety of synthesized molecules, reaction yields, mechanistic aspects of reactions, and future prospects. All the figures are presented in color, highlighting the main reagents, and provide a logical and concise sequence of the key studies discussed.

Figure 1 The use of NaNO₂ in organic synthesis[1`] [b] [c] [d] [e] [f] [g] [h] [i] [j] [k] [l] [m] [n]

Figure 2 Direct nitration (C–H) promoted by NaNO₂, part 1[2`] [b] [c] [d] [e] [f] [g] [h] [i] [j] [k] [l] [m] [n]

Figure 3 Direct nitration (C–H) promoted by NaNO₂, part 2[2`] [p] [q] [r] [s] [t] [u] [v] [w] [x]

Figure 4 Direct nitration (C–H) promoted by NaNO₂, part 3[2y–ad]

Figure 5 Direct nitration (C–H) promoted by NaNO₂, part 4[2ae–an]

Figure 6 Direct ipso-nitration (C–H) promoted by NaNO₂, part 5[2ao–aw]

Figure 7 NaNO₂-mediated nitrosation of secondary amines[3`] [b] [c] [d] [e] [f] [g] [h] [i] [j] [k] [l] [m] [n] [o] [p]

Figure 8 NaNO₂-mediated Nef reactions[4`] [b] [c] [d] [e] [f] [g] [h] [i]

Figure 9 NaNO₂-mediated oxidation reactions, part 1[5`] [b] [c] [d] [e] [f] [g] [h] [i] [j] [k] [l] [m]

Figure 10 NaNO₂-mediated oxidation reactions, part 2[5n–ac]

Figure 11 NaNO₂-mediated synthesis of nitriles[6`] [b] [c] [d] [e] [f] [g] [h]

Figure 12 NaNO₂-mediated oximation reactions[7`] [b] [c] [d] [e] [f] [g] [h] [i] [j] [k] [l] [m] [n]

Figure 13 NaNO₂-mediated heterocycle formation, part 1[8`] [b] [c] [d] [e]

Figure 14 NaNO₂-mediated heterocycle formation, part 2[8`] [g] [h] [i] [j] [k] [l] [m] [n] [o] [p]

Figure 15 NaNO₂-catalyzed/mediated C–C bond formation[9`] [b] [c] [d] [e] [f] [g]

Figure 16 NaNO₂-mediated ring-opening/contraction reactions[10`] [b] [c] [d]

Figure 17 NaNO₂-mediated halogenation reactions[11`] [b] [c] [d] [e] [f] [g] [h] [i] [j]

Conflict of Interest

The authors declare no conflict of interest.

Acknowledgment

The authors are grateful for the postgraduate program in pharmaceutical sciences at the Federal University of Rio Grande do Norte and acknowledge the collaborating members of the pharmaceutical chemistry laboratory of the pharmacy department.

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Publication History

Received: 08 August 2024

Accepted after revision: 09 December 2024

Accepted Manuscript online:
13 December 2024

Article published online:
03 March 2025