Science of Synthesis

Collier, S. J.; Xiang, W., Science of Synthesis, (2010) 41, 669.

Dibromoamines are much less well-explored than the corresponding difluoro and dichloro derivatives. However, there are a number of compounds reported in the literature, with some reliable synthetic approaches available. The isolation and handling of dibromoamines should be performed with extreme caution, as they are often highly unstable to light and heat (even at ambient temperatures). For example, 2-(dibromoamino)-2-methylpropanenitrile self-ignites when left exposed to light on a moist filter paper[‌118‌] and there is a report that N,N-dibromo-2,4,4-trimethylpentan-2-amine decomposes violently.[‌119‌] N,N,N′,N′-Tetrabromoethylenediamine is reported to melt at 62°C, but when heated only a few degrees higher it can explode with a very violent detonation.[‌102‌] As one would expect, tert-alkyldibromoamines exhibit greater stability than less sterically protected derivatives,[‌118‌] and it is recommended that dibromoamines be kept in solution when employed in synthesis.[‌118‌] Interestingly, it has been reported that monobromoamines exist in equilibrium with the corresponding amines and dibromoamines.[‌120‌]

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