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.
Gefahrenhinweise (EU): H225-H302-H332
Highly flammable liquid and vapour. Harmful if swallowed. Harmful if inhaled.
Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. Wear protective gloves/protective clothing/eye protection/face protection. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.