Thionyl bromide

Thionyl bromide
Structure of the thionyl bromide molecule
Structure of the thionyl bromide molecule
3D model of a thionyl bromide molecule
3D model of a thionyl bromide molecule
Molecular arrangement in solid SOBr2 (note that this is dramatically different from the crystal structure of its chloride analogue)
Names
IUPAC name
Thionyl bromide
Other names
Sulfur oxy dibromide
Identifiers
CAS Number
  • 507-16-4 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 61483 checkY
ECHA InfoCard 100.007.332 Edit this at Wikidata
EC Number
  • 208-064-3
PubChem CID
  • 68176
UNII
  • N6CU78B13T checkY
CompTox Dashboard (EPA)
  • DTXSID0060143 Edit this at Wikidata
InChI
  • InChI=1S/Br2OS/c1-4(2)3 checkY
    Key: HFRXJVQOXRXOPP-UHFFFAOYSA-N checkY
  • InChI=1/Br2OS/c1-4(2)3
    Key: HFRXJVQOXRXOPP-UHFFFAOYAY
  • 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[1]
Occupational safety and health (OHS/OSH):
Main hazards
 Readily decomposes in air to toxic gases
GHS labelling:
Pictograms
 GHS05: CorrosiveGHS07: Exclamation mark
Danger
H312, H314, H332
P280, P305+P351+P338, P310
Flash point Non-flammable
Safety data sheet (SDS) "External MSDS"
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).
☒N verify (what is checkY☒N ?)
Infobox references
Chemical compound

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.

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Sulfides and
disulfides
  • Al2S3
  • As2S2
  • As2S3
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Sulfur halides
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Sulfur oxides
and oxyhalides
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Sulfites
  • CdSO3
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Sulfates
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  • Cs2SO4
  • Er2(SO4)3
  • Eu2(SO4)3
  • HgSO4
  • K2SO4
  • KAl(SO4)2
  • NaAl(SO4)2
  • RaSO4
  • SnSO4
  • SrSO4
  • Ti(SO4)2
  • Tm2(SO4)3
  • Yb2(SO4)3
  • Zr(SO4)2
Thiocyanates
Organic compounds
  • C2H4S
  • C2H6S3
  • C4H4S
  • C32H66S2
  • CHCl3S
  • C2H3SN
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