Thionyl bromide

Thionyl bromide
Names
	IUPAC name Thionyl bromide
	Other names Sulfur oxy dibromide
Identifiers
CAS Number	507-16-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	61483 ;
ECHA InfoCard	100.007.332
EC Number	208-064-3;
PubChem CID	68176;
UNII	N6CU78B13T ;
CompTox Dashboard (EPA)	DTXSID0060143 ;
	InChI InChI=1S/Br2OS/c1-4(2)3 Key: HFRXJVQOXRXOPP-UHFFFAOYSA-N ; InChI=1/Br2OS/c1-4(2)3 Key: HFRXJVQOXRXOPP-UHFFFAOYAY;
	SMILES BrS(Br)=O;
Properties
Chemical formula	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
Solubility in water	decomposes
Solubility	reacts in HBr, acetone, and alcohol; soluble in benzene, toluene, ether
Structure
Molecular shape	trigonal pyramidal
Hazards
Main hazards	Readily decomposes in air to toxic gases
Safety data sheet (SDS)	"External MSDS"
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H312, H314, H332
Precautionary statements	P280, P305+P351+P338, P310
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).
	(what is ?)
	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 + 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.^[2] It may occasionally be used as a solvent.^[3]^[4]

Safety[]

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

SOBr₂ + H₂O → SO₂ + 2 HBr

References[]

^ "Thionyl bromide". Sigma Aldrich.
^ 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.
^ 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.
^ 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.

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[1] "Thionyl bromide". Sigma Aldrich.

[2] 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.

[3] 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.

[4] The chemistry of the actinide and transactinide elements. Volumes 1-6 (4th ed.). Dordrecht: Springer. 2010. p. 526. ISBN 978-94-007-0211-0.

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