Thionyl bromide

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Description:
Thionyl bromide is the chemical compound SOBr<sub>2</sub>. It is less stable and less widely used than its chloride analogue, thionyl chloride. It is prepared by the action of hydrogen bromide on thionyl chloride, a characteristic reaction where a stronger acid is converted to a weaker acid:

SOCl<sub>2</sub> + 2HBr → SOBr<sub>2</sub> + 2HCl


Thionyl bromide is used for some brominations of certain α,β-unsaturated carbonyls, and it also converts alcohols to alkyl bromides. Otherwise it hydrolyzes readily to release sulfur dioxide:
SOBr<sub>2</sub> + H<sub>2</sub>O → SO<sub>2</sub> + 2HBr


Safety

SOBr<sub>2</sub> hydrolyzes readily to release dangerous HBr. It also reacts with acetone to give a hazardous lacrymator.

References

Mundy, B. P. "Thionyl Bromide" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York.








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