#bromination

Some succinimide precitipated after a bromination of a toluene derivative using NBS (N-bromosuccinimide).

N-Bromosuccinimide or NBS is a chemical reagent used in radical substitution and electrophilic addition reactions in organic chemistry. NBS can be a convenient source of Br•, the bromine radical.

Bromination using elemental bromine as a bromine source on a relative larger, 0.5 mol scale. On the third gif the product is stirred in the bromine containing reaction mixture and luckily it precipitated, so we only need to filter it. 

Interesting fact from Bromine:  In 1825 bromine had been isolated from sea water by Justus von Liebig who mistakenly thought it was a compound of iodine and chlorine, since it had similar chemical and physical properties to these already discovered elements. Only a year later, in 1826 by the French chemist Antoine-Jérôme Balard described bromine as a new element. He obtained bromine from the manufacture of sea salt at Montpellier by passing chlorine through an aqueous solution of the residues, which contained magnesium bromide. Distillation of the material with manganese dioxide and sulfuric acid produced red vapors, which condensed to a dark liquid.

Bromination using elemental bromine. 

Did you know that bromine is transparent in the infrared region? (above 700 nm) 

Bromination with elemental bromine in acetic acid. 

During bromination with elemental bromine, sometimes a bromine adduct, probably Br2xAcOH or HBr3 crystallizes out what looks adorable, as seen on the above photo. It redissolves/liquefies when the concentration of the acetic acid increases in the vapor (last gif), but it looks great.