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tert-Butyl nitrite is employed as a reagent for diazotization and nitrosation of alcohols, thiols, amines and cycloalkanes. It plays an important role in photocatalyzed conversion of aryl and heteroarylamines to selenides. It finds application in the preparation of aryl azides from aryl amines. It is also useful for radical multifunctionalization reactions of aliphatic alkenes and source of nitric oxide.
Aromatic amines have been converted in good yields to aryl halides in the presence of the Cu(II) halide: J. Org. Chem., 42, 2426 (1977); 45, 2570 (1980).
Zhao, J.; Li, P.; Xia, C.; Li, F. Metal-free regioselective C-3 nitration of quinoline N-oxides with tert-butyl nitrite. RSC Adv. 2015, 5 (41), 32835-32838.
Monir, K.; Ghosh, M.; Jana, S.; Mondal, P.; Majee, A.; Hajra, A. Regioselective synthesis of nitrosoimidazoheterocycles using tert-butyl nitrite. Org. Biomol. Chem. 2015, 13 (32), 8717-8722.
Hazard Statements: H225-H302-H332
Highly flammable liquid and vapour. Harmful if swallowed. Harmful if inhaled.
Precautionary Statements: P210-P262-P301-P315-P310a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not get in eyes, on skin, or on clothing. IF SWALLOWED: Get immediate medical advice/attention.