Tetramethylammonium nitrate is an organic compound with the chemical formula [N(CH3)4]NO3. It is a white crystalline solid. It is a quaternary ammonium salt. Tetramethylammonium nitrate consists of tetramethylammonium cations [N(CH3)4]+ and nitrate anions NO−3.
Uses Tetramethylammonium nitrate is used as a glycolate oxidase inhibitor. It is also used, together with trifluoromethanesulfonic anhydride, to selectively and rapidly nitrate cyclic (number of atoms in the ring is 5 or 6), aromatic and heteroaromatic compounds in dichloromethane as a solvent. An advantage is the removal of undesired byproducts. This very mild nitration is used for large-scale syntheses and gives high product yields that often require no further purification.
Reactions At high temperatures, tetramethylammonium nitrate decomposes to trimethylamine and methyl nitrate.
[N(CH3)4]NO3 → N(CH3)3 + CH3NO3
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