Thionyl bromide is the chemical compound SOBr2. 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,[2] a characteristic reaction where a stronger acid is converted to a weaker acid:[citation needed]

SOCl2 + 2 HBr → SOBr2 + 2 HCl

Thionyl bromide will convert alcohols to alkyl bromides and can be used for brominations of certain α,β-unsaturated carbonyl compounds.[3] It may occasionally be used as a solvent.[4][5]

Safety

SOBr2 hydrolyzes readily in air to release dangerous fumes of sulfur dioxide and hydrogen bromide.

SOBr2 + H2O → SO2 + 2 HBr

References

  1. ^ "Thionyl bromide". Sigma Aldrich.
  2. ^ Booth, Harold Simmons (1939). Inorganic syntheses. Volume 1. New York. p. 113. ISBN 978-0-470-13264-7. OCLC 86223179.{{cite book}}: CS1 maint: location missing publisher (link)
  3. ^ Saraf, S. D. (1 August 1969). "Reaction of thionyl bromide with tropolone and phenol". Canadian Journal of Chemistry. 47 (15): 2803–2804. doi:10.1139/v69-465.
  4. ^ Furlani, C.; Zinato, E. (May 1967). "Hexahalogenoniobates(V), Oxopentahalogenoniobates(V) and their electronic spectra". Zeitschrift für anorganische und allgemeine Chemie. 351 (3–4): 210–218. doi:10.1002/zaac.19673510311.
  5. ^ The chemistry of the actinide and transactinide elements. Volumes 1-6 (4th ed.). Dordrecht: Springer. 2010. p. 526. ISBN 978-94-007-0211-0.

Mundy, B. P. (2004). "Thionyl Bromide". In Paquette, E. (ed.). Encyclopedia of Reagents for Organic Synthesis. New York: J. Wiley & Sons. doi:10.1002/047084289X.rt098. ISBN 0471936235.