Thionyl bromide

Thionyl bromide
Names
IUPAC name
Thionyl bromide
Other names
Sulfur oxy dibromide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.332
Properties
SOBr2
Molar mass 207.87 g/mol
Appearance colorless liquid
Density 2.688 g/mL, liquid
Melting point −52 °C (−62 °F; 221 K)
Boiling point 68 °C (154 °F; 341 K) at 40 mmHg
decomposes
Solubility reacts in HBr, acetone, and alcohol
soluble in benzene, toluene, ether
Structure
trigonal pyramidal
Hazards
Main hazards sensitive to water
source of bromine, HBr
Safety data sheet "External MSDS"
R-phrases (outdated) R14 R20/21/22 R29[1] R34
S-phrases (outdated) (S1/2) S8[1] S26 S30 S36/37/39 S45
Flash point Non-flammable
Related compounds
Related compounds
 SOCl2, SeOCl2;

PBr3, Br2

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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, a characteristic reaction where a stronger acid is converted to a weaker acid:

SOCl2 + 2HBr → SOBr2 + 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:

SOBr2 + H2O → SO2 + 2HBr

Safety

SOBr2 hydrolyzes readily to release dangerous HBr and acts as a lachrymator.

References

  1. 1 2 http://fscimage.fishersci.com/msds/12624.htm

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

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