Tetrabutylammonium nitrite is a tosylate salt. It reversibly binds to copper ions, forming a copper complex that is activated by the presence of nitroalkanes. The binding of tetrabutylammonium nitrite to glycosidic bonds in sugar residues, such as the hemoglobin molecule, leads to the formation of reactive oxygen species (ROS), which are responsible for cell damage. It has been shown to reduce infarct size and improve cardiac function in animal models following ischemic reperfusion injury. This compound also has antioxidant properties due to its ability to scavenge ROS and protect against oxidative stress.
A Tetrabutylammonium nitrite (Bu4NNO2) - acetic anhydride (Ac2O) system was demonstrated to be remarkably efficient for the deanilidation of phosphoranilidates in an oligonucleotide synthesis, i.e., the reaction is over almost instantly[1].
[1] S. Akai. “Tetrabutylammonium nitrite - acetic anhydride system, tetrabutylammonium nitrite, tetrabutylammonium acetate, and cesium acetate - 18-crown-6 for efficient unmasking of alkyl N-phenylcarbamates.” Tetrahedron Letters 39 1 (1998): 5583–5586.
