Thionyl bromide
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Names | |||
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IUPAC name
Thionyl bromide | |||
Other names
Sulfur oxy dibromide | |||
Identifiers | |||
3D model (JSmol) |
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ChemSpider | |||
ECHA InfoCard | 100.007.332 | ||
PubChem CID |
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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R-phrases (outdated) | R14 R20/21/22 R29[1] R34 | ||
S-phrases (outdated) | (S1/2) S8[1] S26 S30 S36/37/39 S45 | ||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; | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
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 will convert alcohols to alkyl bromides and can be used for brominations of certain α,β-unsaturated carbonyls,
Safety
SOBr2 hydrolyzes readily to release dangerous HBr and acts as a lachrymator:
- SOBr2 + H2O → SO2 + 2HBr
References
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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