Free-radical halogenation distribution". For propane and higher alkanes, the hydrogen atoms which form part of CH (or CH) groups are preferentially replaced. The reactivity of the different halogens varies considerably. The relative rates are: fluorine (108) > chlorine (1) > bromine (7 × 10) > iodine (2 × 10). Hence, the reaction of alkanes with fluorine is difficult to control, that with chlorine is moderate to fast, that with bromine is slow and requires high levels of UV irradiation while the reaction with iodine is practically nonexistent and thermodynamically unfavorable. A common method in organic synthesis employing is the Wohl–Ziegler reaction, which
Bromine vigorous fluorinating agent, although chlorine trifluoride is still more violent. Bromine pentafluoride explodes on reaction with water and fluorinates silicates at 450 °C. Although dibromine is a strong oxidising agent with a high first ionisation energy, very strong oxidisers such as peroxydisulfuryl fluoride (SOF) can oxidise it to form the cherry-red cation. A few other bromine cations are known, namely the brown and dark brown . The tribromide anion, , has also been characterised; it is analogous to triiodide. Bromine oxides are not as well-characterised as chlorine oxides or iodine oxides, as they are all fairly unstable: it was once