Thionyl bromide
5199120
183989750
2008-01-13T05:47:52Z
Rifleman 82
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{{Chembox new
| Name = Thionyl bromide
| ImageFile = Thionyl-bromide.png
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| ImageName = Structure of the thionyl bromide molecule
| ImageFile1 = Thionyl-bromide-3D-space-filling.png
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| ImageName1 = 3D model of a thionyl bromide molecule
| IUPACName = Thionyl bromide
| OtherNames = Sulfur oxy dibromide
| Section1 = {{Chembox Identifiers
| SMILES = O=S(Br)Br
| CASNo = 507-16-4
| RTECS =
}}
| Section2 = {{Chembox Properties
| Formula = SOBr<sub>2</sub>
| MolarMass = 207.87 g/mol
| Appearance = colorless liquid
| Density = 2.688 g/mL, liquid
| Solubility = decomposes violently
| MeltingPt = –52 °C
| BoilingPt = 68 °C/40 mmHg
| Viscosity =
}}
| Section3 = {{Chembox Structure
| MolShape = trigonal pyramidal
| Dipole =
}}
| Section7 = {{Chembox Hazards
| ExternalMSDS =
| MainHazards = dangerously sensitive to water<br />source of bromine, HBr
| FlashPt = nonflammable
| RPhrases = 14-20/21-34
| SPhrases = 26-36/37/39-45
}}
| Section8 = {{Chembox Other
| OtherCpds =[[Thionyl chloride|SOCl<sub>2</sub>]], [[Selenium oxydichloride|SeOCl<sub>2</sub>]];
PBr<sub>3</sub>, Br<sub>2</sub>}}
}}
'''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 [[alcohol]]s 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 [[Hydrogen bromide|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.
[[Category:Inorganic sulfur compounds]]
[[Category:Bromides]]
[[Category:Thionyl compounds]]
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